Two decades into his comedy career, Leo Allen is both the host of one of New York’s most popular standup shows (Whiplash) and a busy writer who’s worked for shows like Saturday Night Live, Jon Benjamin Has a Van (which he co-created), Comedy Bang! Bang!, and most recently, Andy Daly’s Comedy Central series Review. Allen recently directed A Night at Whiplash, a concert movie version of his long-running standup showcase Whiplash, which was produced by Splitsider and features appearances from Janeane Garofalo, Eugene Mirman, Michael Che, and more. I recently interviewed Leo Allen about the right way to run a standup show, his stint on SNL, and the John McEnroe ‘80s comedy he’s writing with longtime partner Eric Slovin.
How did you start hosting Whiplash?
I started in the fall of 2008 because Aziz [Ansari] used to host it when it was called Crash Test. And then before that, I think the first [UCB New York] late night standup show was hosted by Sean Conroy and Eddie Pepitone. Maybe that was Wednesdays at first, but at the first UCB, the 22nd Street one. I think that evolved into Crash Test, and Aziz took over when those guys moved. Then, when Aziz was moving, I think [John] Mulaney was gonna do it maybe, but he got SNL and he was nervous about it. He just felt overwhelmed or whatever, so then they just called me and asked me if I would do it, and I said, “Okay.”
I didn’t really want to at first, but then I was like “I shouldn’t have such a bad attitude,” so I did it. I said, “I can’t do it if I have to book it” because I’ve done that so many times before. It’s brutal. I really have a hard time saying no to people and organizing people’s schedules. I knew Jeremy [Levenbach], so Jeremy and I said we’d work on it together.
Are there other shows that you modeled Whiplash after? Little things you’ve taken from different shows?
I think just from seeing a million standup shows and liking some things more than others with the way people ran their shows or the way people hosted… First of all, we didn’t have an audience at first. So I knew going into it that, if this show is starting at 11 pm, I didn’t want to be the kind of host who does five or 10 minutes in between every act. I wanted to keep it moving. Once it got going, I wanted it to really move because I feel like an audience – even an audience who’s ridiculous enough to come out [that late on a Monday], even they get tired. At around 12:30, they’re usually like, “Okay. We’re into this, but…” I think the latest we’ve ever gone is 1:30, but that’s a rarity. I just wanted to keep it moving so the comics have a good audience. Having been on so many shows that go on forever, you can tell the audience just wants to get the fuck out of there.
I never thought of myself as somebody who would be good at hosting or would enjoy it. So I would think of people I liked who host shows, like Mike Sweeney. He’s a Conan writer. He used to do standup all the time. He was such a great host because he would talk to the audience and it wouldn’t be hacky crowdwork. It was interesting.
As far as the show goes, when Luna Lounge started way back in the ‘90s, at first, the idea was you’re not supposed to do your act and people were pretty stringent about that. You could only do stuff you hadn’t done before. People would do stuff that was intentionally not funny; they would just try stuff that was interesting, and the audience knew that’s what it was gonna be. The audience trusted what the tone would be. I sort of wanted that, to be like, “These are people we really like, and they’re just gonna do whatever they want.” Sometimes, that might mean a tight standup set, but sometimes that might mean they’re trying something that they can’t try in a club where people are paying a lot of money and there are expectations. Just from watching Garofalo or Maron or anybody hosting or when I hosted Luna, it was just a fun place. It felt very intimate and conversational. So that was sort of my jumping-off point, although I’m sure I probably didn’t think about it that much.
Are there other things you like and dislike about standup shows you’ve performed at?
Now, I think things are better run than when I was starting. A lot of time, shows are way too long or there’s way too many comics and it sort of feels like an assault. There’s so much standup on TV. It’s almost like an endless supply at this point. I feel like the average person doesn’t understand how much better standup comedy is, in particular, when you see it live. There’s really no comparison. Like, even if you see somebody you love or somebody who’s undeniably great, like Bill Cosby, sure, you loved his special when you saw it on TV. But if you see him live, especially in a smaller setting, it’s gonna be 50 times better. It’s really a “you had to be there” kind of thing with standup, and I think that people don’t really think of it that way.
I feel like people should be the way people used to be with bands, like “I love this band that a small amount of people know about, so I’m gonna support them. I’m gonna go see them live.” I feel like people should do that more with comics. It’s not like Louis C.K. wasn’t unbelievably funny 10 or 15 years ago, or 20 years ago for that matter. It’s so different. It’s so good to see comics live.
Do you have a favorite moment from hosting the show for years?
One time, Moshe Kasher and Brent Weinbach did this bit where Brent would heckle Moshe in the bit from the audience. It was a planned bit, and they had done it a bunch. At our show, one woman in the audience thought that Brent was some guy in the audience, she didn’t recognize him. He was heckling Moshe. She lept to Moshe’s defense. She was like, “Shut the fuck up!” It was hilarious. To a point where they had to stop doing the bit. [Laughs] She was so nice because she was like, “Who are you to talk during this guy’s act? You’ve gotta shut up. he’s doing his thing. You don’t get it! You’re an idiot!” Like, what your fantasy is as a comic of what someone will do for you, this woman was doing for Moshe and ruined the bit. She actually completely ruined what they were trying to do, but in the nicest way.
Did you start doing comedy in New York originally?
Yeah, with the exception of, I probably did it like three times in college at the University of Michigan.
Was college when you first decided you wanted to do comedy, or did you know ahead of that?
I think I knew I wanted to be a comedy writer, but it literally did not seem like a thing that people did. It did not seem possible. I didn’t think of it as a thing to do even.
At what point did you start thinking of it as a thing you could do?
I lived in Israel for a while and then I moved back to the States. I had a couple friends who were gonna study acting. I was just like, “I’ll live with you guys.” I was interested in acting, but that really seemed impossible then, like a waste of time. I kind of backed myself into it. I was in New York and started to go watch shows and then I started to look around. All pre-internet it was very weird. You look in Backstage magazine to find open mics. I think it took me a year to get the guts up, and then I said, “Okay, I’ll go once a week, at least.”
What year was this?
Probably like ‘94 or something. ‘93 or ‘94. That was different. It was really only clubs, and there weren’t a lot of people doing it.
The comedy boom had just crashed at that point, right?
Yeah, it crashed and burned before I started. People who were already super great were Attell and Maron and Todd Barry and Dave Chappelle. Gaffigan was still an open mic-er when I started, he was kind of at the end of it.
Who else was around when you were getting started?
Ted Alexandro, Pete Correale, Dan Naturman. And probably a year after I started, maybe a little less, Zach Galifianakis, A.D. Miles, and Bobby Tisdale – those three kind of appeared together. They all kinda showed up outta nowhere. Oh, Lewis Schaffer. He was sort of a legend. Yeah, I think that’s most of it.
And from there it was, what, a couple years before the Luna Lounge scene started and UCB showed up?
Yeah, at first, Luna Lounge was at reBar on 16th Street, I think. UCB came around, I wanna ‘96 or something. And Matt Walsh actually was my roommate. We lived together for three years or something. And then, the first job where I quit my day job was writing for this internet thing. It was literally the first time I’d ever seen the internet. Literally, they showed us the internet at the job. It was gonna be a comedy website, basically, but the technology wasn’t quite there. The whole original UCB was on the staff – Amy, Ian, Matt, and Matt – myself and [Eric] Slovin, Todd Barry, this guy Mike Lee, this guy Danno Sullivan; we all wrote it.
And then, after about a year, they decided to do it as a live show at Catch a Rising Star. We would do a live show every week that was called whatever the website was called [Ed: The website was called “This Is Not a Test.”] Oh yeah, the guys who sort of ran it was this guy Jim Biederman, who still does a lot of stuff, and Nick McKinney, Mark McKinney’s little brother, and Vito Viscomi. They did a sketch group called The Vacant Lot. They were the head writers. It was their thing. It was with Microsoft or something.
Was it videos or was it text?
It was text, but it was kind of “choose your own adventure”-y. Video on the internet was years away. It was still dial-up. Then, when it became a live show, Maron was the host and that probably went on for about a year or two.
What did you do after that? You were still doing standup and sketch with Slovin, right?
We had some development deal, and we actually shot a pilot for FX in ‘99, I think. We wrote and shot and we were in a pilot, and that didn’t go anywhere, although we did hire Eva Longoria to be in our pilot before she was Eva Longoria.
What was the pilot about?
We were just two guys who lived together. Every episode, our jobs would be different. We reset like every episode, that was the idea. The pilot episode was Eric had gotten these self-help tapes. He wanted me to do them with him, and I thought they were stupid. My life became unbelievably good, and his life became an utter nightmare because of these self-help tapes.
There wasn’t a lot of sketch around New York when you and Slovin started doing it, right?
No, I guess Red Johnny and the Round Guy were a comedy duo. They weren’t really around. They had kind of stopped when we started. The State was really huge then. We started to know those guys, but they seemed famous. We were like, “How are these guys so famous? They have their own show.” And then the UCB came. They had written shows they would do. [A.D.] Miles and Bobby Tisdale would do these weird shows together. Yeah, people would do shows. Slovin and I were pretty consistent for 10 years or so there.
How’d you and Slovin end up working at SNL?
We had been around for whatever, nine years. There were auditions for SNL at the old UCB, which was only sat like 90. We get asked to be on this showcase and it started at midnight on a Tuesday. Our manager was like, “Do characters.” But we were like, “We don’t really do that. We’re terrible at it.” We just did the bits that we liked. It went really well, and it was exciting. Like, Lorne Michaels was there, and it’s cool. Some of the writers were really nice. They came over; they were nice.
We were friends with Horatio Sanz, who’s on the show. He had said that maybe they would be interested in us as writers. So we were like, “Yeah, we’d be interested. Having a job? Yeah, that would be great.” Then, we never heard anything. We were just like, “Oh well, whatever. That was fun.” I think it was like six months later. We were in Edinburgh, doing our show at the Fringe. Eric thought to check his answering machine. There was a message from our managers saying, “You guys got hired. You have to come back.”
Did they have you send in a packet, or did they just hire you off the audition?
No, we didn’t send in a packet. They just hired us off of that, I guess. We were smart enough just to shut up and not ask any questions. We were like, “Okay, let’s not bring that up.”
Were there any memorable characters or sketches you guys wrote on SNL that people might know?
We did “The Falconer” with [Will] Forte. That was our big recurring thing. We had this sketch “Time Traveling Scott Joplin” that I liked, with Maya [Rudolph] playing time traveling Scott Joplin. That was because our office was next to Jeff Richmond, Tina’s husband who did the music. He would have to wait around all night because people would come to him and get him to help them write songs. He was just in his office and he had a keyboard. He was playing ragtime nonstop right next to us. We were supposed to write this sketch that Slovin had pitched, a tennis idea that Lorne liked, and then we realized it was actually a terrible idea. So we had to write something about tennis. That assignment plus Jeff Richmond playing ragtime nonstop for hours turned into that sketch.
Our first week, we had a sketch on, which was lucky. We didn’t realize how lucky that was. It was Matt Damon meets [Chris] Parnell on a park bench, and Parnell’s character’s name is also Matt Damon. He’s a doctor and he’s mad at Matt Damon for stealing his thunder by also being named Matt Damon.
Are you working on the second season of Review currently?
I’m not sure. I think they’re still figuring out the budget and that stuff.
How’d you wind up working with Andy Daly on that show?
They just asked me. I talked to Andy and Jeff [Blitz] about it. Andy was another guy I knew when I started out. He was in New York. He was a fresh-faced young man. Oh, he was in a duo! Andy Daly and Andy Secunda, The Two Andys, they were hilarious. Slovin and I saw them, and we were like, “Wow, that’s great.” That’s when we became friends with those guys. So I guess just from knowing them for so long. They were staffing up, and I just thought it would be nice to have day job.
How is writing that show compared to other shows you’ve written for? It has a pretty intricate structure.
That show is more of a puzzle than other stuff. Jon and I, our show Jon Benjamin Has a Van, we just had to figure it out ourselves. It could kinda be whatever. Scott Aukerman’s show Comedy Bang! Bang! was what it was gonna be, and he had a very clear idea what that was gonna be.
On this show, there was that existing Australian version, so for making our own version, we had to figure out all the rules of the world. There were so many things we had to figure out, like why don’t people seem to know why he’s doing this crazy stuff? Hopefully, we figured out all the questions that you have to answer in a way that if you watch it, you don’t even really notice. We had to philosophically have these conversations about like, “Is there anything he won’t do?” We’d have these endless debates about what it all meant, what were the parameters. It was necessary for what it was. It’s so high concept, but we also want people to be able to just watch it and enjoy it without thinking about it. That was the trick, to find that happy medium where we had figured out what the world really was. If you were someone who didn’t give a shit and just wanted to watch it, you could just watch it.
Did you have a favorite episode from the first season?
Yeah, my favorite is the “Pancakes/Divorce” one. There is somewhere a very long cut of Jessica St. Clair’s breakdown that is one of the great dramatic performances that will never be seen because it was too brutal. Comedy Central – very rightfully, I think – were like, “You’ve gotta be kidding” because you’re just watching a woman have a breakdown. It was like a [John] Cassavetes film. Hopefully, what’s in there is sort of a happy medium. But there is a way longer, darker cut out there somewhere, which I found endlessly entertaining.
You and Eric Slovin had a script for a movie called Superbrat on The Black List last year. Can you talk a little bit about it and what else you’re working on movie-wise?
We’re working on another original idea just for the fun of it, and, hopefully, it gets made. And yeah, we’ve just been talking to a bunch of different people about potential projects to work on, and Superbrat hopefully will be made. That’s the fantasy. We have two unbelievably great producers working on it, a director. I just don’t want to jinx it, talk about it too much before it actually happens. Hopefully, it will be made. For Slovin and I, that would be the hugest, most exciting thing ever.
Can you explain the plot of the movie?
It’s the true story of what happened to John McEnroe at Wimbledon 1980. You’re probably a little too young, but we saw that live when it happened and it was one of the best sports things I’d ever seen. I’m not a huge sports guy anymore, but that was an amazing match, which McEnroe lost actually. But it was a four-hour final. [Björn] Borg was at the top of his game, McEnroe was at the top of his game. But very deadpan, we say this is what really happened: McEnroe gets caught in a compromising position, so the British police strong-arm him into helping with their undercover investigation. So he has to basically work for them while he’s playing.