Writing Craft, Vol. VIII: Rob Wilson and Jason Kypros of Plan B (Part One)

Jason Kypros and Rob Wilson of Plan B sketch comedy and improv.

NORFOLK, Va. — I recently sat down with Jason Kypros and Rob Wilson of the Hampton Roads sketch comedy and improv group Plan B to talk about writing, handling sensitive topics with humor, and the group’s forays into videos — most recently a 10-minute homage to silent film.

Kypros, 33, is a Norfolk native and Wilson, 29, was raised in Chesapeake and Norfolk after his family moved here from Queens, N.Y. Both are writers and actors with Plan B, and both also perform standup comedy.

This conversation was recorded at Kerouac Cafe before Plan B’s recent The Big Show at the Naro Expanded Cinema. It has been edited for length and clarity. There is some adult language below.

Q: Had you wanted to perform when you were kids? How did that develop?

Kypros: I can remember being really little and I just liked to dance all the time. Whenever anything came on, I would just dance. Which is funny because when I was older, you’re an adolescent and you know, I would never dance, but inside I was like, ‘Fuck, I want to dance.’ (Laughs.) But I did a play in first grade, because my dad was teaching where I went to school. Ever since I did that play, I always was kind of doing that stuff.

Q: And at some point, comedy hit you.

Kypros: Yeah. I always loved comedy. … I went to Thoroughgood Inn (Comedy Club in Virginia Beach) before it shut down. I remember going to see a show and being like, ‘I can totally do that.’ But I just didn’t have the nerve to do it. So I moved to L.A. because I got a role in a film. … After a year and a half in L.A., I finally did stand up. I was probably around 23.

Q: What was the film?

Kypros: Mickey. … It was a John Grisham film. I was eligible for my SAG card after the film, and I met a producer and I started working for him. I moved to L.A. and found out intern meant work for free. … I started doing comedy and then started taking courses at The Groundlings.

Q: How about you, Rob?

Wilson: My first play, I can’t remember the name of the play, but I was probably in the first grade. I remember that I played an exclamation point. (Laughter.)

Kypros: I bet you were so good at that.

Wilson: I was. (Laughter.) Like, the play’s almost over and I come busting in. And I say, I’m like, ‘Bam!’ And then after I say my line the (Bel Biv Devoe) song ‘Poison’ comes on. And we all did the dance. (Singing.) ‘It’s driving me out of my mind.’ We all did that dance and I remember I was always do plays in church, and if there was time to speak, I would be doing it. It probably wasn’t until I was 13 or 14 years old, there was this girl, —– ——, and she was like, ‘I love poetry and plays.’ And I was like, ‘Shit, I do too.’ (Laughs.)

Kypros: —– ——, if you’re out there …

Wilson: Thank you. … I eventually started hating her guts. (Laughter.) But like the acting and the poems, that kept up. I decided in high school, that’s what I was going to do. I thought that was all that I was good at, and I’d been doing it since I was 14.

Q: You applied to Old Dominion University?

Wilson: Yeah. I went to (Tidewater Community College) for a minute, and I did some plays over there. I got into ODU. It was like being new all over again. I realized how much I sucked. (Laughs.) When you’re in high school you think you’re great. Then you get to college and you think you suck, and then you get kind of better at it. And then you think you’re great again, and you get back out into the real world, and you think you suck again. It’s kind of this perpetual thing of thinking you suck. I didn’t start doing comedy until I auditioned for The Pushers. And that was six, seven years ago. … (Following a pilot show for The Pushers) I did the very first real show. I was doing a play at the time, Hole In the Sky.

Q: The 9/11 play.

Wilson: Yeah. And – too soon, first. It was like 2003, maybe 2003, 2004. It felt too soon. … I was doing that, so I couldn’t do (The Pushers). So Brad (McMurran of The Pushers) and another dude came to the play and I was giving a heart-wrenching speech to the audience, and they found a way to sit right directly in my eye line, and Brad’s making faces. People were like crying in the audience, and I’ve got to try not to break character. That’s when I decided comedy might be fun to do.

Q: Did you go to school locally?

Kypros: I went to Norfolk Academy for 12 years. My dad taught there at the time, and then I went to college at Virginia Tech. It was pretty much right after college that I got that movie. That’s when I went out to Los Angeles. I lived in Los Angeles for about six years.

Q: What did you study at Tech?

Kypros: I was an interdisciplinary studies major.

Q: What does that mean?

Kypros: It’s almost like a choose your own adventure major. You take your minors and you turn them into an interdisciplinary studies major. My minors were theater, communications and the humanities. I didn’t get accepted for the engineering curriculum but I took engineering for the first year and half … and I was like I don’t want to do this anymore. … The theater minor happened because I was doing so much production. I was in a lot of plays, and you kept getting like a credit every time you did a play. I was like, ‘Shoot, I might as well take a couple classes and get the minor, you know?’

Q: What kind of plays? Was it comedy?

Kypros: No. Actually, I love musical theater. We did some cool stuff, man. We did some experimental stuff based upon a Kurt Vonnegut novel. Comedy always ended up coming up. You’ve got to know when to hit those beats. When you’re performing live, it becomes something you can feel. It’s not always the same thing. You know it from seeing things that make you laugh. It’s like, if that would have been a second sooner, I wouldn’t have laughed that hard. Timing is –

Wilson: Is everything.

Kypros: Is everything. Timing and life are both a bitch. (Laughter.) Timing is a bitch.

Q: So how did you do with standup?

Kypros: The first time I got up, I said to myself, ‘I’m going to do the edgiest stuff I have.’ I got up there, and it was some pretty decent stuff. I have joke about my mom being adopted. Some of the jokes I still tell today.

Q: What’s the joke about your mom being adopted?

Kypros: It’s just like people , when they get on stage, they want to say, ‘Well, I can say this because my mom was this or I can say that because my mom was that.’ You know, but my mom was adopted so I don’t know what she brings to the table. You know, the only way I’m going to find out is if I run for office or something. So I’ve had to look at my life and see if there’s any clues to show me what it is that she brings to the table. I realized that ever since I was 13 I’ve always had a job, so maybe I’m white. But at every job I’ve ever had they’ve always complimented me on my fantastic work ethic so I could be Mexican. I get my check and I don’t want to spend it so I might be Jewish. And I love white women so I must be black. And that was the joke. … The first time I got up and told these jokes, people laughed and this guy asked me if I wanted to do this show at this place that was down on West Pico Boulevard, the Comedy Union next to the Roscoe’s House of Chicken ‘n Waffles in L.A. It was like a bringer show. (The comic has to bring friends to fill the audience, and there’s often a drink minimum.) But it was cool. It was one of those moments where you got up, you did it, it was great, and then the guys says, ‘Hey, I run the show. You want to do this thing?’ You know, so that was neat. That worked out pretty good.

Q: How hard is it to fill the bringer shows? Did you have willing victims?

Kypros: Yeah. You have some friends. It’s always something like bring five friends or eight friends. But the thing was always, it’s a $10 cover and a two drink minimum. So it was hard to constantly hit your friends up, and they hear you telling the same jokes a lot. … After a while, you realize I can’t keep doing bringer shows. As a hungry comic, you want to do all the work you can do, but then you get to be a little wiser in your craft and you start to see what it is. You start to see the benefit of the open mics and then you say, ‘Well, maybe I only need to do one bringer show every three months and really bring ‘em out.’ … You almost inadvertently get a schooling in self promotion.

Q: You’re writing your own stuff.

Kypros: Yeah. Absolutely. My brothers and I have a great relationship and so every now and then they’ll call me up and have a funny idea, you know what I mean? There’s some jokes that I have that are certainly thanks to my brothers and there are jokes in there that are thanks to my friends too. You know, as comics you’ll sit around and go, ‘Oh, here’s a tag. In that joke what if you said this?’

Wilson: We were just having a conversation last night on the way to the show and somebody said pee-pee.

Kypros: I said pee-pee.

Wilson: And I said please don’t – there’s nothing sexy about referring to my penis as pee-pee, and we just spit-balled for like, what, twenty minutes on the way to this show. When we got to show, it killed.

Kypros: Yeah, I got up and started doing this bit and it worked. That’s how you write, I think. That’s how I write. The way I write the best. Riding in my car, thinking about something. You know, riding in my car by myself, it’s almost like I’m working. My head’s running, I’m thinking about stuff, and I’m putting stuff together. There’s nothing better than having a buddy there you can bounce stuff off of.

Wilson: Yeah. That’s a good thing. That’s actually the best stuff ever.

Kypros: Road tripping is good times.

Q: When did you start writing?

Wilson: I started in poetry and spoken word. … I started writing probably my senior year of high school for real. My buddy and I thought we were filmmakers and (laughs) we would do just horrible stop-motion effects and stuff like that … I was 22 before I wrote anything good. Everything was terrible up until that point – writing this hugely emotional, what we thought was avant-garde crap for years. But when I started writing comedy, started writing sketches all the time, that gets you to train that muscle to start thinking in that way.

Q: And for comedy to work, it’s got to have a shape.

Wilson: Right.

Q: You got to have the assumption, you’ve got to deflate the assumption and build toward the final turn. I know I’m not using the terminology.

Kypros: I don’t know what the terminology is.

Wilson: My favorite thing is incongruity. I learned this back in high school. One of these things doesn’t belong here. One of these things doesn’t work. You know what I mean? And then under that same kind of notion, what if something is completely out of place and no one acknowledges it?

Kypros: You put normal people in a strange situation or –

Wilson: Or you put strange people in a normal situation.

Kypros: You play with levels and all sorts of stuff.

Wilson: Truth’s the best thing, though – stuff that really tells the truth. That’s what I liked about the “Light Rail.” I didn’t even thing it was so funny. It was funny because it was so true.

Kypros: To me, that’s the whole reason I wanted to do comedy anyway. I grew up listening to Eddie Murphy, Robin Williams and George Carlin, but George Carlin was the one I really liked the most, I think, because I thought he was hilarious and he dealt with issues. He dealt with the way people thought about things. Everybody’s dealing with the way people think about things because it’s comedy, it’s the juxtaposition, but I just thought it was so cool. It was like, ‘Many a truth is told in jest.’ How many times has someone been, ‘Hey, you’re an asshole. Ha ha. Just kidding, man.’ Man, you mean it. (Laughter.) I like to say that standup comedy is the last bastion of free speech, or it should be. Which is why I tell that joke about my mom, because to me it’s ridiculous. We’re sitting here laughing and it’s like so what, I get to say this thing or that thing or this word or that word or I can say this scenario just because I have this card to say it? You know, if you’re going to say it, say it. The thing about it too is it’s what makes you laugh. You’ve got to hit that thing. Again, with the light rail, they’re thinking that. They’re already thinking it. And you’re saying it.

Wilson: We gave them a voice.

Q: How did this group start?

Kypros: I had done The Groundlings and I was back in Norfolk and I had always wanted to do – I felt like when I came back I wanted to do some sketch comedy. … I got to meet Rob and Brad (McMurran) and all those guys (through The Pushers), and Sean (Devereux) and everybody … Well, we kind of were buddies before I saw (Wilson) perform. I thought it was really awesome what they were doing everything and we all became friends and were hanging out and all that kind of stuff. … I had always kind of wanted to do something, but I didn’t know what it was. I ended up going back to L.A. after I came back (to Norfolk) to finish the class at The Groundlings, finish this last whatever. Now I’m a level four Groundling. It’s like a role-playing game or something. That was the one where they really taught me how to write. That was the one where the whole idea was look at all this improv training you’ve done – use it to write the sketch. Use it to fill in the blanks in the sketch. Which is really like we were doing already, where we’re riding in the car, BS-ing in the car, and suddenly I’m up on stage telling a joke, only it’s written, you know?

Wilson: Right.

Q: But if you want to go long form, and I think it’s the same as a story, there’s a shape. It’s got to go somewhere. We’ll (discuss) that with “Light Rail,” but how do you get to that place? The inspiration seems to be the improv, but at some point if you want it to be –

Wilson: With that sketch specifically, there was an idea. We were thinking, ‘Well, what’s on people’s minds?’ I think that’s where it started. And then we were –

Kypros: We were bullshitting about the light rail, is what it was. We were just talking about how stupid it was, and we started laughing, and … we just kind of looked at each other.

Wilson: Aha. That’s it.

Kypros: We had just started the group. I had come back and I’d done a couple plays at Little Theatre of Norfolk and Brendan Hoyle was the director there. He and I together were like, ‘Let’s start this thing. What do you want to call it?’ (Hoyle and Kypros then started Plan B.) Rob and I had talked about doing stuff together and it was the sort of thing where we were all talking about stuff but there was never the opportunity for us all to work together.

Q: So why did you leave The Pushers?

Wilson: I wanted to be a part of this group because Jason and I work together and we have a really great time. We have great chemistry. It’s fun. It’s like a little bromance. (Laughs.) And he’s like well we’re doing this thing, and we’re going to be shooting a lot of stuff, and it was always something I was really interested in. I thought a lot of subject matter was going to be different from what I was doing then. So I was like I want to do this thing, and (The Pushers) thought it would be a conflict of interest. (Though Wilson wanted to do both, he realized there was no way he could have split his time.)

Kypros: When we started Plan B, we had like eleven or twelve people. We had an audition. Thirty people came out. We didn’t expect that many and we had to choose 12 of them, and now … we’re down to nine. That’s how it goes. Cause it’s hard, man. No one’s making money.

Wilson: We’re doing it for the love.

Kypros: We knew that everybody had different levels of experience as far as what they’d done with improv. One of the things we talked about from the very beginning … we wanted improv to be the foundation of the whole group. The sketches would come out of that. It’s fun. You’re constantly creating. We’ve done a good job with it and we’ve tried to help each other along. Our rehearsals are like a class.

Wilson: Almost, yeah. Definitely.

Kypros: We have an agenda. Rob’s been making sure we stay on task with that.

Wilson: We all are on different levels. Jason’s gone all the way through The Groundlings. Lauren’s completely Second City trained. I’ve been doing it a while. I haven’t –

Kypros: You’ve had influences from all these different things.

Wilson: I’m like a ronin. I’ve learned a little bit from here, a little bit from there. All of us will tell you, every single rehearsal we go to, we learn something new.

Q: (Wilson and I) have talked personally about content. In my own writing this is something I’ve struggled with (in short fiction stories). One of the things we’ve had conversations about, is when you’re creating art or a sketch – and I think what you guys do is art – how do you deal with that issue of how you’re representing people in sketches?

Wilson: We did a racism sketch. Sometimes I think it’s what’s not said but how the characters themselves are portrayed. So in the racism sketch, I’m a black dude who has his own hang-ups and ideas and Brendan’s a white dude who has his own hang-ups and ideas. Both of the characters are coming from an intelligent place with an intelligent argument, even if their foundations are completely off base. What I’m saying is we’re not playing any one character in a way that –

Kypros: We characterize a specific point of view and the point of view points out the ridiculousness of the situation.

Wilson: Right, but I’m saying in the portrayal of the characters. Not just in the content. I think a lot of it has to do with the portrayal of the character.

Q: Both characters – and they say completely off-base things – but they both have power.

Wilson: Right.

Kypros: They believe what they’re saying.

Q: It’s a dialogue, it’s not –

Wilson: Right. It’s not, ‘You’re telling me how it is.’ And I’m just sitting here taking it or vice versa. It was honorable.

Kypros: It was an honorable dialogue.

Q: Until you got to Asians, but we’ll come back to that.

Wilson: Right.

Kypros: Right, but come on.

Wilson: (Kidding.) We don’t have any in the group, so they couldn’t speak up.

Kypros: Nah – Again, the point was to add to the ridiculousness of stereotypes and that sort of stuff.

Wilson: Right.

Kypros: That was the idea. Like for all those things, you’re talking about content and what we want to get across, I know for me – I have a production company. That’s how we started doing all these video things. I have a small production company, JLK Productions — there it is. That’s all the plug I’ll do. … But so basically, here I am, I know how to do this sketch stuff. The cool thing to me about the sketch stuff was, you know, this is what I was writing. I was coming out of The Groundlings writing all these sketches for stage and thinking, ‘Some of these would be good video sketches.’ To me, SNL and the stage and that whole concept – I really got a taste of that when I was doing that class. I mean, three months of that. So this was what I wanted to do. I knew I wanted to do Plan B and I knew we were going to have video influence from the beginning. … Keith Jackson started helping us out. He helped direct “Light Rail.” He and I directed it together, and he directed the racism PSA. … With the racism PSA, as far as content is concerned, we knew that – I knew that I wanted to keep it at a certain level. As a standup, I hate it when you go to work a room and they say, ‘You’ve got to keep it PG.’ I don’t know why. I feel we all live rated-R lives, and it’s ridiculous to pretend otherwise. You might stub your toe and say ‘shit.’ That’s the world we live in. So I’d rather be honest, but I don’t want to push it. But with the racism PSA, there definitely were some moments where we all as a group were like, ‘Well, how should we play that line?’

Wilson: I feel that when you’re talking about, especially, racial stuff or anything that’s kind of touchy, I go back to truth, man. Like, if it’s true, let’s play it from an honest place. That’s coming from an actor and a writer’s place, but, I guess, more as an actor because you want to play the honesty. We were cautious of certain things because you don’t want people to get the wrong idea. Because when you do something that’s touchy, when you do something that can go either way, there becomes a concern. (Comedian Dave) Chapelle was talking about it. He was talking about when he was doing his show … he did (a sketch about a family whose last name was a racial epithet) … He did the sketch and it was hilarious to him, but he would go to some backwater place and people would come up to him and be like, ‘Ha ha ha, (repeating the epithet) yeah!’ And it was like, ‘Why are you laughing?’

Q: That’s kind of what I’m getting at. Could someone watch that sketch (“The Folly of Racism”) and enjoy the fetishization of Asian women at the end of it?

Wilson: I think the point that it’s placed, it’s tongue-in-cheek enough – If they did, it’s a far reach.

Q: Right, but you think the sketch reads that, obviously, it’s satirizing both stereotypes and sometimes the ways we talk about stereotypes.

Kypros: Right. What Rob’s saying about truth and what we said about putting ridiculous people in real situations or vice versa is what you have there is you have two people who are characterized, and they themselves are playing stereotypes and they believe it’s their truth and it looks like a PSA. That’s how you get the funny in that sketch. It’s like (singing the NBC public service announcement theme) ‘The more you know … ’ So we have this real situation and we’re putting ridiculous people in it. So that’s why I don’t have a problem with the Asian joke because we’ve established that these two people are ridiculous. You know what I mean? So they say that joke and it’s like some place for them to – so the subtle way is it’s like bringing them together. You know what I mean?

Wilson: It’s like this common ground. And the thing I’ve realized is somebody dumb is gonna take whatever you say and feel whatever way they want to about it. But you know what you’re intention is. As long as you’re clear on your intention as an artist or as a group of artists –

Kypros: There you go.

Wilson: – then, I mean, you give it to them and it’s all subjective.

Kypros: You can’t make everyone happy, right? … Not everybody’s going to laugh at a comedy show the same way.

Wilson: The thing that gets weird is when you’re dealing with a group of artists and you don’t know the group’s intentions. You know what yours is. If you don’t know the group’s intentions, that’s where you get into a muddy place.

Kypros: We make sure, I make sure, Brendan makes sure that once we had everybody after the auditions we told everybody what our intention was.

Q: What is your intention?

Kypros: Our intention is just to be a really good sketch comedy group. Plain and simple.

Wilson: From top to bottom.

Kypros: We want to have solid stuff and we want to be able to appeal to a wide range of people. We’re not trying to go for one particular group. With my standup, it’s different. I go to do my standup and I want to say whatever I’m going to say and I want to do it however I want to do it. But with this stuff, I am more inclined to go, ‘Well, will the kids laugh at it?’ Like the silent film. (‘Follow That Fiend!’)

Wilson: We did the silent film at the Naro, and children were enjoying that. You know, it’s nice. Oh God, it’s so nice to be able to have something you can have your mother and children enjoy. You know I don’t have any kids yet – that I know of – but when I do I want them to be able to enjoy the things that I do. With my standup, my standup my kids are not going to enjoy. Until they’re 20. (Laughs.)

Kypros: You might not want them to hear it.

The next part of this talk is on the way.

Playing us out … a terrible song about an L.A. institution to which Kypros gave a shout out above. Enjoy the insincere dancing.

P.S. Plan B did not do this video.

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2 thoughts on “Writing Craft, Vol. VIII: Rob Wilson and Jason Kypros of Plan B (Part One)

  1. […] NORFOLK, Va. — I recently sat down with Jason Kypros and Rob Wilson of the Hampton Roads sketch comedy and improv group Plan B to talk about writing, handling sensitive topics with humor, and the group’s forays into videos. Here’s the second part of that talk. The first part is at this link. […]

  2. […] comedy. Wilson, of Chesapeake, recently was featured along with Plan B’s Jason Kypros in a discussion of comedy writing you can find at this link. Barnes, of Norfolk, is a veteran comic who I hope to speak with here again down the road. […]

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