36 min read

Stumble Into Brilliance (Rachael Mason)

Honesty, self-improvement, comedy, and surreal reality.

Rachael is a comedian and legendary Chicago performer and teacher from Chicago's The Second City and The Annoyance Theater.

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Simone Salis (host): Where are you originally from?

Rachael Mason (guest): I'm from New York.

Sim: You're from New York? So you're not too far from Miss Messing, who's originally from New Jersey.

R. Mason: She's from New Jersey.

Sim: I'm sorry.

R. Mason: She… I love her, but she's from New Jersey.

Sim: That's a foreigner thing. I would have never dared to offend you. Or anybody-

R. Mason: Although, she makes fun of me-

Sim: Why?

R. Mason: -because I'm from Long Island. Not Manhattan.

Sim: Oh, well. That's terribly good? Terrible…?

R. Mason: It sort of puts me on the… back on the same status as New Jersey.

Sim: Oh okay. Okay. That's why you're very good friends.

R. Mason: Yes, absolutely. Absolutely.

Sim: Long Island is the New Jersey of New Jers- no, what? What is… I'm not sure.

R. Mason: Yes. Yes.

Sim: So you're originally from there, but, When did you move to Chicago?

R. Mason: I moved to Chicago the day after I graduated from college.

Sim: You were waiting for it?

R. Mason: I was. My college improv troupe, the Ad-Liberal-Artists, shoutout Skidmore, go Thoroughbreds. my college improv troupe was founded by David Miner, and David Miner is the guy who produces, like, Brooklyn 99 and 30 Rock and Parks and Rec.

Sim: Oh.

R. Mason: So, needless to say, he was a very motivated dude. And he… He started the National College Comedy Festival. So I got to see, like, The Purple Crayon of Yale and, like, all these incredible improv- Mick and Del came in. And every time somebody great came in, I was like, "where… where did you come from?"

Sim: Is that? Yeah…

R. Mason: And they would always say, "Chicago." And, I had grown up on S. C. T. V., cause I have real cool parents, and once I joined my college improv troupe we all moved to Chicago together to sort of seek our fortune at the Second City.

Sim: Okay and you all mov- How many of you?

R. Mason: Fi- about five of us.

Sim: Five of you. Okay. All right. Did you guys start to live together, or….

R. Mason: We did. Ana and Lauren had already moved here…

Sim: Uh-huh [affirmative]

R. Mason: So me and Jed slept on the floor there. And then, I slept there until I found an apartment. Slept in an empty studio until I had enough money to buy a couch.

Sim: That's always good.

R. Mason: Slept on my couch until I had enough money to buy a bed. And then I had a friend from college come in to visit, and they bought me a kitchen table and chairs.

Sim: Nice! So, buy now you should be living in, like, a regal… Like, you have all the-

R. Mason: [laughs] A palace? Like Susan's house? I am not there yet.

Sim: [laughs] I've not been there, but… [laughs] nice. So you moved here because… Did you… Did you get to take classes with Del,

R. Mason: So, I say I moved here for Second City, and what I say is I moved here for… for improv. And, the person I was most interested in was Del Close. And long-form and Harold… Like, we taught ourselves Harold from a book. But then, getting here and, like, hearing it from the man who invented it was incredible. so I immediately started taking classes at all three places at the same time. Annoyance, Second City, and iO.

Sim: Wow.

R. Mason: All at the same time. While working a nine-to-five day job.

Sim: What was that?

R. Mason: I did all kinds of things. I was a bookkeeper, a bank teller, I worked at DeWitt Consulting, Chicago Shakespeare Theatre…

Sim: Mm-hmm [affirmative] Well, your degree, was… you were majoring in Shakespearian Theater, right?

R. Mason: Yes.

Sim: Yeah, so that… That makes sense. [laughs]

R. Mason: Yeah, but I was the bookkeeper at Chicago Shakespeare.

Sim: Okay. Okay. Well, okay. That's getting there. Like the couch, it needs upgrades.

R. Mason: Let me tell you, working on Navy Pier is the freaking best.

Sim: Huh.

R. Mason: I would, like, have a beer and a brat and ride the Ferris wheel at lunchtime. It was incredible.

Sim: I guess if you work there, it's true, but-

R. Mason: Yeah.

Sim: -if people visit, you're like, "Let's… let's not necessary…"

R. Mason: "We're not going to Navy Pier." "Yeah, it's beautiful. We're not going."

Sim: [laughs] "It's great. Let's not go there." But, Okay, so you started to do all of that and the classes at the same time.

R. Mason: Del was still alive. You had to work your way up to him.

Sim: Huh.

R. Mason: The Annoyance, there was no audition, I just started in… Pretty much in Level Two there. I got asked to do a show. I started Second City, made it through their first audition, made it through their second audition and then dropped out-

Sim: Ha ha, rebel.

R. Mason: -to go do a show at the Annoyance-

Sim: Uh-huh [affirmative]

R. Mason: -and then ended up doing, like, three shows at the Annoyance. And they got a little bit of attention, so then I got invited to the private Second City auditions.

Sim: Ah.

R. Mason: To the invite auditions, and I… Even though I'm head of three departments at Second City, I never graduated the conservatory.

Sim: [laughs] I want to high-five you from afar. Yeah. [laughs]

R. Mason: [laughs] Boom!

Sim: okay. So, you… Oh, my god. Such a rebel. You got here and dropped-

R. Mason: Well…

Sim: You know, there are expectations and… Including myself, partially, but… People get here to Chicago, and they go, like, "I'll do the whole Second City thing. I'll go on a boat, and I'll…" Well, not anymore, but… [laughs] Like, I'll stay off the…

R. Mason: There was talk of a murder mystery train contract with Amtrak. Isn't that the worst? That's the worst.

Sim: Ah, we're going all the way back to early '90s and Schaumburg tourists.

R. Mason: I can't.

Sim: we're going to talk later about who's going to manage that and… [laughs] how… But, Okay. I would go on that. No, I wouldn't. It's like Navy Pier. [laughs]

R. Mason: Well, actually, I did a cruise ship.

Sim: Oh, you did?

R. Mason: And I always thought to myself, having been on cruises when I was a kid… My family loved to do cruises, and you'd watch the entertainers, and I always thought to myself… Kill myself, kill me if I am ever an entertainer on a cruise ship.

Sim: Boom.

R. Mason: It was the best fucking job I ever had.

Sim: Of course.

R. Mason: It was so much fun, traveling all over the world, being a pirate… Meeting incredible people.

Sim: Nice.

R. Mason: I had-

Sim: So, you'd do that, like, for how long? For, like, a…

R. Mason: So I had a special contract. I was running iO.

Sim: Uh-huh [affirmative]

R. Mason: But also touring for the Second City.

Sim: Uh-huh [affirmative]

R. Mason: So, the normal contract is usually for months. But registration periods are two months long. So, Second City and Charna sort of went to, like… Like, had a little bidding war over me.

Sim: Did they?

R. Mason: And they decided… Oh, it was so, awesome. It was like, "Yeah! Yeah!" so… Second City agreed to put it in between two registrations…

Sim: Huh.

R. Mason: -which sucked for me. I left at my busiest time, and I got back to my busiest time. And, while I was on the boat, it was incredible.

Sim: Mm-hmm [affirmative]. But then, it was all of a sudden… [laughs]

R. Mason: Thrust back into it.

Sim: Hmm. How was… So, you're… you probably had expectations of what taking a class would be with Del? Or, it was something you wanted for yourself.

R. Mason: I knew that moving to Chicago would make it easier to go back to New York or L. A.

Sim: Ah.

R. Mason: And, frequently, when you're in Chicago… Like, they come to you.

Sim: Mm-hmm [affirmative]. That's weird. [laughs]

R. Mason: Lorne Michaels comes to the Main Stage twice a year.

Sim: Mm-hmm [affirmative]. Yeah. Well, Charna makes all the things of, like…

R. Mason: Charna has her showcase. Even… Even Nick's showcase at iO is killing it. Tons of people… Well, most of the Main Stage and maybe even the E. T. C. are Annoyance-trained.

Sim: Hmm. How do you see this thing of expectations… Like, at this point, there is thousands of… [laughs] improv students at the same time, probably. And, considering also who visits for intensives, and those kinds of things. And some of them might have the dream, which is perfectly healthy to have. I'm not sure, like… How healthy are expectations, because the numbers of making it in that way with Rush Showcase, with Learner's, those things…

R. Mason: Something like 3000 people audition for Tour Co and only two get it. Like, that's crazy.

Sim: Something like that.

R. Mason: Right? And out of this three Tour Cos, only two of them might get Main Stage?

Sim: Mm-hmm [affirmative] mm-hmm [affirmative]

R. Mason: And out of five Main Stage productions maybe three of them will go up to Saturday Night Live? You don't get all the parts you want.

Sim: No.

R. Mason: You don't get everything you audition for. You can't always perform with the people you want to perform with. But, the City of Process as opposed to City of Product.

Sim: Uh-huh [affirmative]

R. Mason: Like, people get good here.

Sim: Uh-huh [affirmative]

R. Mason: That's why they're great when they go to those other places. That's why those other places come here to look at us.

Sim: Chicago…

R. Mason: Although, now U. C. B… Like, why get on a plane to Chicago when the U. C. B. is right there in New York? Although… Cause they're all movie stars now, right?

Sim: [laughs] Yeah.

R. Mason: And they are moving even the Del Close Festival to L. A. Because that's where…

Sim: Easier for them.

R. Mason: Shoot movies, put up our T. V. shows. I always thought I was going to be a comedic Broadway actress.

Sim: Hmm

R. Mason: So, I loved musical comedy and performing and I did… Like, auditioned for Annie when I was a kid.

Sim: Huh.

R. Mason: And, when I got to Chicago, like, I was quickly, like, typecast as, like, you know… The pretty girl's best friend and the comedic roles. The old lady, the sassy lady next door.

Sim: The funny one.

R. Mason: Uh-huh [affirmative] Exactly. And, I was allowed to, via improvisation play everything I would never normally get cast as in real life. Right? I could play Abraham Lincoln, or a samurai, or a Somali pirate. And then, channel that into the roles that I would normally be cast in and give my characters depth.

Sim: So, you had the chance to explore more eventually than you would have had with conventional…

R. Mason: Yeah.

Sim: -routes and that.

R. Mason: Absolutely.

Sim: And you also created… Crafted the training programs at the iO.

R. Mason: Yeah.

Sim: So, especially when you started, which was mid '90s, something like that? Yeah. I would say that not a lot of, I wasn't there, but, you know… Not a… Not an excessive number of women are in advancing proposition right now, so I can only imagine…

R. Mason: Girl!

Sim: [laughs] How was that? I don't… I don't want to have the story, like, "Yes, it was terrible," but…

R. Mason: All right, I'm going to be a shit right now.

Sim: [laughs] do it.

R. Mason: So, I'm Italian.

Sim: Oh, are you, though? This isn't…

R. Mason: I'm half-Irish, half-Sicilian. My family is from Polizzi Generosa in Sicily. So, why I studied Shakespeare is… I realized that, like, there was an inherent misogyny to my culture. I mean, it's typical to the Mediterranean, quite honestly. So, my focus of study was Shakespeare's Rome. I was like, "Why is this place… Why is… Why are Italians the way they are?" And then I paid attention to, like, The Rape of Lucretia, The Rape of the Sabine Women, like… All of a sudden, I was like, "Rome was built on the backs of women." I realized that if I could make all these old Italian men playing sette e mezzo laugh-

Sim: Uh-huh [affirmative]

R. Mason: -I would not have to go to bed. My brother and sister would already be upstairs, and I would be doing, like, my Mae West. Or, like, telling jokes, or whatever. And… Like, everyone sort of… sort of, like, acknowledged that, like, "Rachel is entertaining this demographic that is very interesting." So, when I moved to Chicago, I was like, "Fuck you, old men." "I know exactly how to make you fuckin' assholes laugh," right? And I wasn't, like… It didn't bother me being the only woman in the room. I didn't know that it was supposed to be different because I liked to claim my space. The men in the room, however, have…

Sim: Heh.

R. Mason: Have different feelings about that. And, certainly when I started… Well, when Susan started she was the only woman. By the time I started, there was, like, a woman on each team. Each team had a woman.

Sim: Oh, it's the woman quota, like the gay quota. Or the black quota.

R. Mason: Mm-hmm [affirmative]. Uh-huh [affirmative] But then, because I… I like to say that my ability eventually caught up to the size of my balls. Because I had huge balls, I started getting on more and more teams, and better and better teams, and… Dave Pasquesi says, "If you're the best one on your team, you're on the wrong team," right? So, I kept moving up and learning and…

Sim: Great.

R. Mason: These great people were pulling me up, and I got to… Like, I got to watch Amy, Rachel, and Tina. And, like, that's a master's education right now. And they didn't give a fuck either. And Del Close, who is known as a misogynist and was, but I can forgive that as a product of his time. Tina Fey said this, "Del really wasn't a sexist, he just hated wusses. He hated anyone that didn't make a hard choice." And I was not afraid to make a hard choice. I'd be like, "Boom! I made a choice." And he was like, "What's your name?"

Sim: Recognizing that he was acknowledging that…

R. Mason: Everyone was afraid of him, but I was like, "Whatever, you're another gross old man." I'm a New Yorker. I'm Italian. Right?

Sim: Like, "Fuck everybody. I don't care."

R. Mason: Fuck everybody! Eat something, but fuck you.

Sim: Of course. Yeah. I'm going to do this, this…

R. Mason: Yes.

Sim: And, And I am doing it.

R. Mason: Yes.

Sim: And I'm doing it well, and you guys just enjoy it.

R. Mason: Yeah.

Sim: [laughs] good times.

R. Mason: And then I get on Baby Wants Candy, because they're like, "You can sing." And then I get invited to do a show, and then… I have this, like, philosophy that if you're the kind of person people want to work with they'll work with you. And if you do good work, you will get invited to do other good work. What I really had was commitment. I was going to go whole-hog, and back then… Like, there was a piano player named Dave Adler, and he was incredible. And whenever he saw me onstage, he'd, like, walk me right into the key I could belt in.

Sim: [laughs] He knew.

R. Mason: That's great.

Sim: He knew.

R. Mason: Lisa McQueen can do the same thing. She knows Jonathon Wagner. Knew exactly what key I could belt in. Steph McCullough.

Sim: Oh, yeah. Sure, sure. She used to… Well, is the M. C. L. still there? No? Okay, no…

R. Mason: Although they do run Mint out of the Annoyance now.

Sim: Nice. Nice. Okay. For whoever doesn't know, these are all improvised musical shows which are insanely hard and insanely beautiful with talented people to see. You can literally… I think I cried a few times at M. C. L., it's just… Is…

R. Mason: It's beautiful.

Sim: It's just beautiful.

R. Mason: I saw them improvise Sondheim there and fully wept.

Sim: It… That… That's exactly where I was just… I couldn't contain it anymore. I was just like, "I'm going to cry." It's a room full of talented musical directors and singers, they're making it up in the moment and working together. And it's just a lot. [laughs]

R. Mason: Well, I think that sense of ensemble… Like, the band is as important as the singers is as important as, like, the main character and, like, the backup characters… Like, in Chicago, we understand, like… It's the group making a thing. Not, "Look what I did to help make the thing." Which is why we are so successful when we go to other places. In writing rooms, on Broadway, directing… Like, we are able to understand all the sides of the die.

Sim: Mm-hmm [affirmative] That's such a hard thing to do. Like, I think when you start to improvise… As a person who has only started to improvise, but never, like… Did more, that… that's the hardest part, because at some point it's beautiful to get a glance of it. I don't say that I get it, but, like… To glance at it. And I think it's also beautiful to see… How is it for a teacher? Like, when you see people getting that… that…

R. Mason: Nothing turns me on more than watching somebody go, "Oh-oh." I'm like, "Yes!" Not, like, sexually. But, like… It's like, Art can save the world!" But… Like, what we know in improv is it won't always be good. It'll be interesting, but it won't always be good, which is why when we see great improv, we're like, "Holy shit." And even in great improv, like, it's not laughs per minute. They stumble into the moments where, like, the audience empathizes, sympathizes, or gets educated, and then they laugh. Release the tension. When a team stumbles into a moment of, like, brilliance. Here is the laugh. We're like, "Yay," and younger teams see that and are like, "Laughs per minute. Laughs per minute. Everything must be funny." Instead of, like… The laugh is the exciting thing that we're chasing. And, like, the more you reach for it, the further it moves away from you. The more you stay where you are… Like, it comes to you, right? Like, everyone thinks every line has to be funny, and I do not think that is true of improvisation. I think things have to be specific and emotional, and that will always produce funny.

Sim: Hmm. Inevitably, you think… It's almost… If… If you're truthful and honest, you… eventually through emotion you will… It… the fun will come out of it, like, maybe in a more profound way…

R. Mason: This is a really weird example. Susan and I are doing this show… Like, it's fine. Like, we're doing good. And we're in a scene where we're fighting each other. And, we're in a kitchen and I go to slam the drawer, and Susan goes, "Self-closing drawers."

Sim: [laughs] What?

R. Mason: And the audience started laughing for, like, five fucking minutes.

Sim: [laughs] Yeah.

R. Mason: And Susan and I look at each other like… "Self-closing drawers the thing that-" "like, brought down the house?" And what we found out is there was a group of women in the house who had just come from some lady's kitchen where she had self-closing drawers. And they were all like, "Tee hee! Oh my god!" And their reaction is so big it made everybody else laugh. Right?

Sim: It was contagious.

R. Mason: Like, who knew?

Sim: Audience is a stupid thing, like self-closing… It's just like…

R. Mason: Well, they do suck in an argument. You cannot slam them.

Sim: Yeah, you… Yeah, that's true. It's like, "All right! Fine!" And it makes no noise. Which is great with improv because I'm sure your objective was great, but hopefully you were not making the noise of a drawer, like…

R. Mason: No, it doesn't make a noise, right?

Sim: It's self-closing. Like that?
How much do you think, you know… This learning about… That it's all our work together and it doesn't matter to chase the laugh was in Del's teaching because…

R. Mason: Del didn't care about funny. Del cared about truth. He said the whole reason we took a suggestion was to learn a… So the audience would learn a truth about it, and that we the team would learn a truth about each other in the pursuit of that thing. So, remember. He started at Second City. Satire is about the truth. Why is it the way it is? Skepticism. So, even Harold was a way to, like, roll a suggestion like a die. What does it mean? First suggestion is war, we're going to explore peace. I'm going to play chess, not be a soldier, right? To sort of, like, see what war means and deconstruct it. He was at… He knew from Second City that the byproduct of improvisation will never not be laughter. Comedic or dramatic, because you are never not fucking with expectation. You're making it up. You're always fucking with expectation, so laughter will be a byproduct of that.

Sim: And touching truth.

R. Mason: Yes. Right? Oh, yeah. I recognize that, or I get that reference, or I've been through it… I've been through that, sister. Right?

Sim: I… I'm so fascinated by this approach, because on one side, if you get that part and get to live that part even just once out of six years, seven years, whatever… it is a beautiful moment. It's a beautiful feeling, getting… You have this feeling of creating an understanding with other family members, almost, out of that. And that is what I love about Chicago, is like… It is… this is what, like, it's a magnet. I came here the first time and I kept coming back and I kept coming back and I kept coming back and I kept-

R. Mason: [laughs] I know.

Sim: Fine. I'll be here. And eventually… Will not do improv, but that is a beautiful thing.

R. Mason: But… But I bet improv affects your life outside.

Sim: Oh,

R. Mason: Every day.

Sim: 200%. 200%. And, I… I'm really not worried… I'm really observant how there is a tiny part of me that goes, like… There is a danger that we might turn the word improv in the moment to… into something you just say, like, mindfulness of meditation, that kind of stuff…

R. Mason: [sighs]

Sim: The mantra of that, because what you're talking about…

R. Mason: I don't think you're wrong.

Sim: Oh. Okay.

R. Mason: Lots of people think improv is a cult already, and Del was a weird, psychotic…

Sim: Well, the stories about… Yeah… Well, like…

R. Mason: Ruler.

Sim: Ru- yeah, whatever, it… I… Yes. I don't know how much of that is built to sound like that so you can-

R. Mason: To mythologize it.

Sim: -sell it. Yeah, to make the myth. Like, the Steven Jobs of Improvisation. That kind of, like, thing of making Apple a church and improv a church- And selling more… Yeah. But, I recognize-

R. Mason: We make art. We make art.

Sim: Okay. Okay.

R. Mason: That's what we do. Satire tells the truth. Comedy turns trauma into laughs, right? Like, our pain is other people's, like, release of tension.

Sim: Hmm. Hmm. Common threads, stories that we recognize and parents like that. So, okay. Del was not… Well, he was insane, but he wasn't a cult leader.

R. Mason: He was totally fucking crazy.

Sim: Okay, he was?

R. Mason: But not a cult leader. He didn't fucking care. Like, he would separate a class into, like, thirds. And… Not thirds. There would be two people, usually men, that he'd be like, "You're incredible."

Sim: Hmm. Mm-hmm [affirmative]

R. Mason: And then there'd be another group that was like, good but, like, whatever. Like… you're good, who cares. And then there was the third group of, like, "You suck." "you are terrible and you should not be here."

Sim: He was up front about this.

R. Mason: He would literally turn his back on two thirds of the class and turn to those people and be like, "You can do anything," and all of these other people fell into two camps. "I don't need him to tell me I'm good, I'm going to learn," and, "What about me?" And, like, fuck them anyway. I got lucky, even though I'm a woman, to be one of those people that he was like, "You can do anything." "You can take over the world." And when you think about who was sitting there… Amy, Rachel, Tina… The U. C. B… Like, they did take over the world. Like, they run entertainment right now. Adam McKay, you know… All those early Harold teams… They are running this business.

Sim: Hmm. Yeah. And… Yeah. So, the thing is that he mostly didn't care about… He didn't want to waste time with bullshit.

R. Mason: Correct.

Sim: That's the thing.

R. Mason: Correct.

Sim: That's the thing.

R. Mason: Although he was known to wax philosophical. Like… When I had him, it was towards the end. We were his last… We were his first 5B team, and his last full class. He would cough for 20 minutes. He would talk about the Cuban Missile Crisis for 20 minutes. And then he'd go, "Two people up." And you'd be like, "What the fuck does he want?" And I'd be like, "Cuban Missile Crisis, communism, group mind, fascism. He's equating communism… fascism, to group mind." So I got up on stage and I did a scene, like, "All right, Privates. Line up." And, like, after the scene was over, he goes, "Exactly!" And I go back to my chair like, "What the fuck?" Right? And people would be like, "He talks so much! And he…" And I'd be like, "Listen to him. Listen to him. And listen to what he's not saying. Listen to what he's trying to trigger in you to think about." At Second City, they cared about showing off if they were, like, smart.

Sim: Hmm. Yeah.

R. Mason: Not if they were funny. Right? And smart doesn't mean, like… The capital of Bulgaria is Sofia.

Sim: So that…

R. Mason: Which it is.

Sim: Good job! You're smart!

R. Mason: Thank you. It means I know what I know.
And I am unafraid to share that. So, Del loved when people played to the height of their intelligence.

Sim: Mm-hmm [affirmative]. I remember, like, reading… Or even somebody saying that about, like, kids or… or crazy peo- if you play a kid, play the kid at the top of their intelligence of the character-

R. Mason: The kid's smart, the kid knows everything you know.

Sim: [laughs] Yeah.

R. Mason: Here, I'll be a regular kid. Ask me a question.

Sim: What… What do you think of death?

R. Mason: that's… I want my Mom! You're… That's horrible!
Okay, now ask me that same question again.

Sim: What do you think about death?

R. Mason: Well, karmically speaking, If you behave in this life then in the next life, you might reincarnated as, like a butterfly because you were a good person in your last life. Although, I… you know, I… I… Existentialists believe there is no afterlife, but that's still believing in something. See what I mean? Like, all of a sudden, like… That other kid can't follow the action of a scene. This kid can.

Sim: Mm-hmm [affirmative]. Yeah, you-

R. Mason: If I want to play an old person, I'm not going to be like, "But I don't know who you are?" And, "I shit my pants!" That is the most dramatic part about being old. There is nothing funny about that. So, my old person is going to be like, "Well, I don't know. I… I just don't think that Jennifer Lopez and A-Rod are good together."

Sim: [laughs] Great, yeah. Yeah. You know, of course. Do… Giving the dignity of… and humanity to anybody.

R. Mason: What I realized Del meant is playing to the height of your intelligence means your characters know everything you know. You just get to chose whether they share that or not.

Sim: Hmm. And in which way?

R. Mason: Uh-huh [affirmative] So, Del loved this. I loved to play to the height of my intelligence, I think I've told you this story before. It's a scene where I'm onstage with a girl and she's actually a doctor. And, I was thinking to myself, like, "Oh, shit. She's a doctor. She's going to kill this scene, because our suggestion was 'hospital.'" And then I was like, "Oh, fuck." I am not a doctor. I'm going to look like an idiot standing next to her. What am I an expert in? Teddy Roosevelt? Great. So, she goes, "The bullet went in through the brain, right through the cerebral cortex. We have to be very careful here. Center of speech and movement." So I say, "Ah, yes. Panama Canal. Dig with extreme caution." And she goes, "But it exited here, through the medulla oblongata. We still don't know what it does, we can be a little more careful there." And I go, "Ah, yes. San Juan Hill. Charge away."

Sim: [laughs] Wow.

R. Mason: And the audience wasn't like, "Doctors don't talk like that," the audience was like, "Those doctors fucking rule," right?

Sim: Yeah. Nice.

R. Mason: And, because my scene partner wasn't like, "What's wrong with you, Teddy Roosevelt?" They were like, "Yes! Absolutely, we can dig here." Yeah.

Sim: There you go, digging-

R. Mason: So, like, I'm not a doctor, but I could use my expertise in something else to still be an expert doctor. That's what I think playing to the height of your intelligence means. I think that's what Del meant.

Sim: [sighs] Wow. Okay. That's hard to do, but eventually… you know…

R. Mason: Have confidence in your skill set?

Sim: Yeah, if you're confident… Yeah.

R. Mason: All right. So…

Sim: No, don't do that!

R. Mason: So.

Sim: Don't do that!

R. Mason: Our art form was literally invented for children to be successful at. Children lack a filter that adults have. Fear is a learned behavior. Fear is a learned behavior. Like, kids are going to fail. So, when Viola Spolin's son was like, "What are we…" Like, "Let these adult people… Let's try and play these games," they slammed into that brick wall of fear and judgment. And realized that they had to try to play as fearlessly as kids but simply bring to it their adult intellect, their reference level, their emotional depth. Play like a kid, but with all the bullshit you've learned as an adult is an incredible way to think about this art form. I think it's very freeing.

Sim: It is… it is, and it's incredibly hard to do after you grew in a system and in a society that structures you for 20 years between education and social situations with that and it's beautiful, but it-

R. Mason: It's why a certain tribe is drawn to this work, right? A certain tribe is drawn to this work. Charna says it's not checkers, you don't just smash pieces around. It's chess. There is strategory, not a word, strategory in, like… If you make a move, I can do this, or I can do this. Right? Which is why we, like, try to agree right away, so then we can just have a conversation. We can have discourse. We don't have to talk about being little kids, we can talk about the fiscal cliff being imaginary, and all of a sudden our scene is satire without even trying. Because you and I can talk about the financial crisis as adults, and then our kids look as though they are parroting their parents behavior. Look at what they learned from their parents. Which makes that scene literally satire without trying, for out of the mouths of babes comes great wisdom.

Sim: How many years have you been doing this?

R. Mason: Two.

Sim: Two! [laughs] Sorry, I didn't mean to laugh. Are you still, like… Thinking you still love it like if it is the first 10 minutes…

R. Mason: Yeah, you bet I fucking do. You moved halfway across the world. I moved halfway across the country cause I believe in this art form. This work started in giving voice to the voiceless, helping children to understand this new world around them, to acculturate without assimilating, and for that work, Jane Addams became known as the Mother of Social Work. The second Neva Boyd and Viola Spolin came in… Like, the art form blew up. It… It let children make art about the world, and when the adults tried to do it… They realized that play had to be re-learned, which is why Second City is, like, "Let's just play, don't worry about being funny. Show me what you know and how you feel about the world."

Sim: How do you make people understand that? Hey, you got closer with the microphone.

R. Mason: I scream it at them.

Sim: You scream it [laughs] Are they intimidated?

R. Mason: Yes. [laughs]

Sim: Good.

R. Mason: Which is why I don't teach Level A, right?

Sim: You need to…

R. Mason: I need to not teach Level A.

Sim: You need to filter people so they're ready for getting screamed…

R. Mason: That's why I created the Dramatic Improv program. So I could do serious work. It's why I created… Like, the Scenic Improv program is about reps and point of view. I like that higher-level stuff. Not that I don't love seeing people learn…

Sim: Yeah, yeah.

R. Mason: That agreement, and "we're a team," and "make a choice." Now I'm very interested in, "Make best choices." Choices that lean into social and political satire.

Sim: So, what do… So, for best choices, you mean in a constructive way for a Second…

R. Mason: For Second City.

Sim: Yes. Correct.

R. Mason: Because the goal of Second City is creating…

Sim: Improv to Sketch.

R. Mason: Improv to Sketch. iO is stand-alone improv that will never be seen again. And Annoyance is like, "We do whatever the fuck we want."

Sim: Okay. And, did you… Did you keep in mind this difference when you created, like, the program at iO first and then you moved to the Second City and started…

R. Mason: Because I created the iO curriculum, I could not, like, rip myself off. And realize that iO is impermanent improv, the kind of improv we're doing at Second City, we're trying to see if it can stick around. So, while they all start in the same place, truth and grounded character, eventually they go off to very different purposes. So, like, already there… I couldn't teach long-form the same way at Second City that I did at iO. Like, this long-form will never be seen again. This long-form, how do we harvest this scene, right? How do we do this scene over again?

Sim: Uh-huh [affirmative]

R. Mason: Long-form for generative purposes, as opposed to, like, funny 30 minute show. I have been doing this since 1996. That's not including college, which I learn… College doesn't count. I'm sorry. Like, it just doesn't… College teams don't count. You get here and you're like, "Oh ho! Okay." So, '96… what is it, what… 2000… I've been doing this for twenty… Ahem, mah-mah years.

Sim: Mah-hur-hah?

R. Mason: Uh-huh [affirmative]. You're making me happy, cause I am… I do still love it, like, when I…

Sim: You literally do.

R. Mason: When I first saw it.

Sim: I think… Susan Messing says a thing… We're turning improv into rocket science…

R. Mason: It's not!

Sim: It's fucking not.

R. Mason: It's not.

Sim: I mean… If you want, but…

R. Mason: It's "Listen to your friend." All these rules, rules, rules! It is "Listen to your friend." That is the only improv rule that is important.

Sim: [sighs] Not exact… It's how I'm feeling for myself, and now… Just, you know… Just studies about behavioral change that happens with improv and all those things-

R. Mason: It helps autism. Anxiety. We just did a study with the University of Chicago, it's helping Alzheimer's and Parkinson's patients. Like, it's actually re-wiring their brains. It just got very dramatic in here.

Sim: Just getting background.

R. Mason: I love it.

Sim: So… So how did you… Dramatic Improv. I wanted to take that with you, you dared to get sick when I signed up, how dare you…

R. Mason: Don't fuck with me, I got really sick, okay?

Sim: I… I'm going to respect that, but one day I might have to take the… And, no offense for whoever was your sub or anything, but I was like, "I… I'm going to come back when Rachel…" But, again, they were totally amazing, but I was like, eh, let me know when Rachel is back." [laughs]

R. Mason: I created the program. Of course you want to take it with me. So, what I perceived was a hole. I perceived a hole that the majority of expectations on our improv was that it had to be comedic. So, I wanted to create a space free of comedic expectation. Just improv. Just good scenes.

Sim: Uh-huh [affirmative]. How relaxing is that, without the pressure of comedy?

R. Mason: And they were still fucking funny. Right? The release of tension, right? Good drama has trag- a good drama has comedy, and good comedy has tragedy, right? It's… Like, you need them, like an oil painting, to make depth. So, this is interesting. Like, getting kids to, like, pull back from scratching for comedy and just being, like, a mother and son. Can… Like… Can we just do that, please? Susan and I went to Sweden to teach a workshop there. And we're like, "Comedy, comedy, comedy!" And we start watching their scenes, and I realize that, like… When their scene skews dramatic, they didn't care. They went that way.

Sim: Huh.

R. Mason: And I was like, "Yes!"

Sim: Bless you!

R. Mason: "This is heaven! This is heaven!" Like, not clawing for the comedy, but seeing what the scene really is… A simple, sweet relationship scene between a father and son, and that can be funny enough. So, when I came back, I started looking at satire differently. I started looking at scene work differently. And I thought that… Like, a Second City running order, like, can't be the same three and a half minute, laughs per minute, scene. You need long and short and dark and light and fast and slow.

Sim: Right, right.

R. Mason: You need… Like, you need a sad scene, cause that dick punch scene right after? Like, they… It makes them both better, right?

Sim: Yeah, you…

R. Mason: Dick punch.

Sim: The dick punch! no… I don't know… The work that, improv is often associated with comedy any… In mass culture…

R. Mason: Besser would say…

Sim: Ha, yeah.

R. Mason: Like, it must… It should be funny. That is the point.

Sim: It has to be funny.

R. Mason: He loves shitting on Chicago improv.

Sim: I don't… Good for Matt.

R. Mason: He came from here! Shut up. I love you, Matt.

Sim: [laughs] I, How is that macaron? Good?

R. Mason: Ifs-immuh-fun.

Sim: [laughs] I'm glad. I'm going to have one too, fuck it. Well, the work that you do and Susan does and you guys do together… It was so great to see Susan back onstage together with the… I keep laughing and eating lemon macaron. Enjoy that, Just talking and eat it.

R. Mason: Yum.

Sim: Oh, what the hell?

R. Mason: Why did you pick such a sticky food for this?

Sim: I don't know. Up until today this show wanted to be something corny and N. P. R.ish sound, but now… I'm just eating macarons in the mic. Stop it!

R. Mason: These macarons are amazing.

Sim: Stop it. I don't know what I was talking about anymore. Thank you very much. Yeah, the voice. You make it worse. What do you make worse, everything…

R. Mason: Susan has this terrible example, and it's not P. C. and totally horrible.

Sim: Fine.

R. Mason: So, not only am I breaking up with you, but it's raining and your parents are there. And you have Down's Syndrome, and you're on death row.

Sim: Ew.

R. Mason: I know, I told you, it's terrible. It… So, like, that is how… Like, worse… We could still make it worse than that.

Sim: I… Please do. Just one or two levels of worse. Do it for me, I just want to…

R. Mason: This is where it's on death row, and, the person who beat you up in high school is the executioner.

Sim: Oh, no.

R. Mason: Right? And, at the same time you're getting electrocuted, Lighting hits you in the dick.

Sim: In the balls [laughs]

R. Mason: [laughs] cause it was raining.

Sim: Right, it was raining. Yes.
All right. Fine. They're both… you definitely made it worse, or worsester…

R. Mason: It's like, "How's your husband?" "I don't know, how is he?" Like… Oh, you just told me I'm fucking your husband. Great. Cool. Let's make it worse.

Sim: I love that usually in your shows… the first time that I saw Susan in Messing With a Friend… At some point, you were in it… In, like, a version at iO. She wasn't doing it at the Annoyance. And then there was, like, a special edition at the iO for some reason… I love those… Politically uncorrect, it was… I do, because I think that you need to look at the intention of the people, and the goal.

R. Mason: Uh-huh [affirmative].

Sim: I don't think that being politically correct is necessarily good. I think…

R. Mason: To do a scene about racism, you might have to play a racist character.

Sim: That's… That's the thing. And it's not that you are racist.

R. Mason: Nope.

Sim: You're just portraying somebody-

R. Mason: I am sending up racism. I am not trying to do a racist scene.

Sim: So, the end of the day you're punching up.

R. Mason: Yes.

Sim: As we say, you're literally, like, showing what bad there is… Politically, socially, something.

R. Mason: Yeah. Yes.

Sim: Not always on purpose. Sometimes you just got a… get a hunch of that you need to play along with it… of course, if you're enjoying that you're having a great time because you can't be a racist openly during the day, well, fuck that. But, [laughs] But, you know, you need to…

R. Mason: It's going to take a lot for a racist to change their point of view, you know?

Sim: Yeah, exactly. But, yeah. And that is… I think sometimes there is the danger of… I think some… some things would be considered… Considered, like, politically not correct now, and that was not the intention-

R. Mason: It was a different time. Even the Annoyance, the grittiest place in the world, doesn't run Co-ed Prison Sluts anymore. I mean, everything about that show is… Like, the worst, Worst-est-est-ist.

Sim: Well, yeah, Susan also talks about it, and… [laughs]

R. Mason: Right? I mean, they did a… They… I mean, nothing was taboo there. And, very recently they did a show, and I can't remember… Something… We would consider very benign, Mick had to apologize for. And he was like, "Ooh, even in this place where everyone knows there's no rules, there are new rules." Like, Around pronouns and gender and race and communication, like… Like, this is… This is a… This is a… Again, a not-P. C. and very bad example-

Sim: Yeah

R. Mason: -of it, but, like, in the back… Back in the day, everyone used to be like, "Oh my god, that's so retarded," or "Oh my god that's so gay," And what they meant was like, "That's stupid," or, like "that's weird." and now that is simply unacceptable to say. And when you play those characters like, all of a sudden is it… like, the theater responsible for your hate speech?

Sim: Right.

R. Mason: Or, can audience really see that the characters are assholes and those assholes talk like that.

Sim: Here's the thing. The… the… If you just use that during the day to go and offend people about who they are, that is… that is… that is just despicable… Like, I… I am gay. When I was in high school and somebody yelled, "Faggot," I was like, "Hmm, no." The first few times I was offended by, and then it was like, "I… I… I don't think you can do that."

R. Mason: No.

Sim: I think can… It's my prior… but, But…

R. Mason: It's like how I feel when I get called a honey in a meeting.

Sim: Uh-huh [affirmative]. Yeah. You are a honey, you can say honey, but… Who calls you a honey in the middle… Does that happen?

R. Mason: Yeah, it still does.

Sim: It still does?

R. Mason: Fuckin' old white men.

Sim: That is most of corporate America, but… Yeah, but if it… Like, you know, if you completely eliminate these kinds of characters and talking about the things that-

R. Mason: You can't do satire anymore.

Sim: You can't do satire, and you risk empower… Empowering this thing that's making them more powerful.

R. Mason: Absolutely.

Sim: I think… because you're…

R. Mason: I totally agree.

Sim: It's just, like, not how it is… You… you were eating a macaron, but you're not anymore, so I'm going to put your microphone back…

R. Mason: Hello.

Sim: [laughs] Back there. so, you have one child. How politically correct are you around your child? How old are you child?

R. Mason: He's nine. All right, I'm going to tell you something. I can't believe I'm telling you this.

Sim: Yeah, do it.

R. Mason: So, Susan got me a gift. It's one of those pop socket things that goes on the back of your phone so you can, like, hold your phone.

Sim: Oh, yeah. Yeah, yeah.

R. Mason: Right? And it says, "Fuck Trump" on it.

Sim: Cool. I guess, for you…

R. Mason: Right? I forget, and I put it down because I'm doing something and my son picks up my phone, and he goes, "Mommy, what does this spell?" "F-U-C-K" and then I hear my husband from the other room go, "You know what it spells." And my son looks at me, he goes, "Can I say it?" And I was like, "All right. Once. At the same time. And we have to high-five when say it."

Sim: What the heck…

R. Mason: So me and my kid both go, "Fuck Trump!" And then… and then I was like, "And we can never do that again, not outside the house," Right? Like… Like, I get… I love that you get it, kid. But also, you are a child. And I have no desire to, like, impose my political will on you.

Sim: Right. Good. [laughs]

R. Mason: We… So, I was raised by somebody who did not think language was taboo. Like, you could swear in our house as long as you used it right.

Sim: What do you mean by used it right? How do you discern…

R. Mason: You couldn't be like… Like, "This is a real fucking mess," as opposed to, like "What the fuck are we going to do today?" Right? Like, my father, he was a Marine so he, you know… he used to say things like, "Shitbirds, drop your cocks and grab your socks, it's time for breakfast."

Sim: Oh, great.

R. Mason: He still calls my son a shitbird, and… He… My son is like, "Grandpa, yay!" I… We tend to keep the news off when he's awake. if he asks us a question about the world I try to answer him honestly. Without scaring him.

Sim: Very hard.

R. Mason: It is. It is very hard.

Sim: Only because most of what the news that goes around and you can see on T. V. or anything… it's centered around the fear of those…

R. Mason: I mean, well, he sees something that's like, "A Race War Is Going To Begin," or like, "Trump Fans…" and he's like, "Mommy, is there really going to be a war?"

Sim: That's exactly how you start the war. You convince people that there is going to be a social war.

R. Mason: Right? We're, like, nine steps into fascism right now. "So, there have been lots of war through history. Remember, we learned about the American Revolution?" "And sometimes we need to change things. Mommy thinks we can do things via discourse. Mommy thinks we can talk things out. Mommy's ready to fight…" "But Mommy thinks that… Like, we can figure this out politically."

Sim: Mm-hmm [affirmative] "Mommy thinks that improv is fun," [laughs] And doing nice things on stage [laughs]

R. Mason: Oh, my god. Oh, my god. Susan and I did a scene once about the end of the world where we were two ladies in a bunker… And, like, the… We could see the bomb coming at us, and as the first time that something like this happened- Susan stayed inside the bunker and I opened the door and I faced it.

Sim: Accepting the inevitable.

R. Mason: Yep. Yeah.

Sim: Here, gigantic tsunami! Take me with you! [laughs]

R. Mason: We should be lucky for it to be that painless. Instead of some zombie epidemic.

Sim: Beautiful sight. [laughs] There might be, you know… I don't want to go too dark, but if we keep, like, melting ice some ancient virus might just pop out… [laughs]

R. Mason: I just read an article about that.

Sim: Yeah, it's…

R. Mason: That flora and fauna that haven't been seen for millions of years are now coming out into the environment. And we have no idea what they will do to us.

Sim: [laughs] Maybe they'll say "Hi." They'll start to talk.

R. Mason: Or they could get in their little planes and be like, "Bye."

Sim: Bye!

R. Mason: "You can keep this shitty planet."

Sim: They're like, "See ya!"

R. Mason: Uh-huh [affirmative]. So long and thanks for all the fish.

Sim: Right. [laughs] It… what…

R. Mason: So in the same way that I said I wo- always wanted to tell my child the truth without scaring them, I say that I always wanted to teach what Del taught, but not how he taught it. He was merciless and mean. I think this art form is meaningful. I do believe that, while I can't teach you to be funny, I can teach you to do a better scene and that will produce funny. I think that this is an art form that was invented to give voice to the voiceless and to engender teamwork. And, like… I'm sorry, our world needs that right now. I think satire is very important. Anyone who thinks they know it all is a liar. Because the art form itself is changing, the art form itself is evolving. As language evolves, as society evolves, this art form is different… Noah says this, Noah Gregoropoulos, he's like, "I'm older than this art form." I was like, "Ah ha ha, you're old. Ha ha, you're old."

Sim: But it's true, also…

R. Mason: But it's true, right? This started off as short-form competitive games, and now we have everything from short-form to long-form, dramatic, scenic, like… This art form will continue to fucking change. And we have to change with it.

Sim: Comedians that you like growing up and now, forms of comedies, sketch, something that you like and you bring with… Like, whatever you take… I don't know what that reference, but…

R. Mason: I had super cool parents, as I said.

Sim: Uh-huh [affirmative]. That's

R. Mason: So I got to listen to S… I got to watch S. C. T. V., I got to watch Monty Python. I got to listen to Redd Foxx and Richard Pryor.

Sim: Oh, man.

R. Mason: Records… I got to listen to Lenny Bruce records. Beyond the Fringe, like… They were so cool They were like, "Here are these great things." I remember… I mean, Bill Cosby was… used to be a thing. I remember having a Bill Cosby album, a Father Guido Sarducci album, I had every George Carlin album. And then, when it comes to movies, like I'm… I'm basically, like, Brooks-ean by default. Mel Brooks is my hero and king and I bow down to him. Do you know that Blazing Saddles and Young Frankenstein were made in the same year?

Sim: I did not know that.

R. Mason: Isn't that fucking amazing?

Sim: [laughs] I'm not surprised you like so much the truth and the… and the chari… the caricature like between the…

R. Mason: Well…

Sim: Monty Python and Lenny Bruce and Mel Brooks.

R. Mason: Monty Python sat… Monty Python's satire. Lenny Bruce wrote for Paul Krassner's satirical magazine.

Sim: Speaking of which… The old iO… yes, and, At the old iO, I remember when I first came here in 2011 I walked into the Del Close Theater, and there was a poster of Paul Krassner and Del Close doing a show together.

R. Mason: Yep.

Sim: And from Italy, I was like… I thought I was the only person knowing Paul Krassner… And I come here and it's, like, there, like I'm in the right place.

R. Mason: Yes. Yaaas, queen.

Sim: From Italy. okay. Gross things.

R. Mason: Gross things?

Sim: I… Yeah.

R. Mason: Okay, so this happened very recently. My son is talking to me, and while he's talking to me he casually picks his nose. And he's standing in a doorway, and he casually, like, wipes-

Sim: No!

R. Mason: -his hand… booger down the wall.

Sim: Just casual.

R. Mason: And I'm like, "Dude, that's so gross." And I look at the wall, and I notice there are, like, six more.

Sim: Oh, no! No!

R. Mason: And I was like, "Oh, no. I'm gross. I didn't notice that this is my son's booger wall?"

Sim: [laughs] no…

R. Mason: It was so fucking gross.

Sim: What happened, Rachel? How did…

R. Mason: Cause little kids are disgusting. Little boys are gross.

Sim: I know.

R. Mason: Now he eats them, and you catch him eating them…

Sim: He eats them?

R. Mason: And he's like, "What?"

Sim: All right. All right. Too gross.

R. Mason: Ha!

Sim: I can't take that. I can't take that. That's cause you're here. What do you do? You have regular classes at the Second City, too? You teach, well, Dramatic Improv. Which people need to have a little bit of experience… Not too much.

R. Mason: Hmm-mm [negative]

Sim: No? Zero? Just go and be real.

R. Mason: Yeah. It'll be easier.

Sim: It'll be easy.

R. Mason: Cause you're not a bullshit actor, you're real.

Sim: You're like, "I'm going to be funny and please my ego and the audience at the same time today." [laughs] Sorry. That's me, by the way. It's not anybody else's. Miss Mason, today with macarons and real life. A trip. Thank you so much for being here today.

R. Mason: Thanks for having me.

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