From The Comic's Comic

How the man who wrote “How To Be The Greatest Improviser On Earth” found his way into improv in the first place

Will Hines was a seemingly mild-mannered computer programmer at the turn of the century when his Y2K bug for comedy kicked in — he took classes at the Upright Citizens Brigade Theatre in New York City when the UCB was still young and impressionable itself. Two decades later, Hines not only has become a dignified character actor in sitcoms and late-night TV — his credits have included Brooklyn Nine-Nine, Kenan, Broad City, Search Party, Inside Amy Schumer, Unbreakable Kimmy Schmidt, Adam Ruins Everything, Crazy Ex-Girlfriend, Community, Conan, and Jimmy Kimmel Live. He’s also a well-respected improv teacher in his own right, turning his Tumblr into a book on the subject, “How to be The Greatest Improvisor in the World,” and teaching workshops such as “Find The Fool.”

When I caught up with Hines earlier this month, he was preparing to perform stand-up and teach a workshop called “Fool vs. Voice of Reason” at the North Coast Comedy Festival in NYC.

Here is an edited and slightly condensed transcript of my conversation with Will Hines !

Sean L. McCarthy: What would the UConn student version of Will Hines think of this version of you in your 50s, doing stand-up comedy and teaching improv workshops?

Will Hines: Oh yeah. Man, what a nice question. I think he’d be really impressed and happy to see it, probably also terrified for me. I was so far away from it when I was in college I was basically like a journalist. I mean, I was a journalism student, and like very scared of that. In college, I jumped around. I was a chemical engineering major and an economics major and a math education major and then I backed into journalism in my senior year. Because I was interested in it, but also just like my credits kind of added up that way. So I was very directionless. To see that I had gone into any kind of performing at all would have shocked me. I didn’t get on stage until I was 30. So when I graduated from UConn, I was still nine years away from stepping onstage.

I mean I’m sad as a journalist, that we lost you to comedy. But seeing what you’ve done in the last 20 years I’m grateful that you chose comedy.

I was adding nothing.

Who started improv first, you or your brothers?

Me. I started first. I was the oldest so they would kind of copy me a lot, and then vary it up from there. So our mother died when we were kids, or I was 16, they were 11 and nine. We got very tight because of that and so, I do think they imprinted on me more than younger brothers imprint on older brothers, usually, like I’m a huge Beatles fan there Beatles fans. I’m a Red Sox fan, though we were in Yankees territory, they sort of copied that. They’re quite different than me now, but I do think when they were younger, they sort of copied me and then made variations as needed.

So did they also take to either journalism or computer programming?

My next youngest brother, Kevin, when he first moved to New York City I got him a job at my company. He came to my improv theater and took classes and then eventually took my job at the improv theater.

So he’s done the best job of being imprinted.

Yes, yes, I mean they are quite quite different now. But I want that credit because sometimes they get grouchy with me and I’m kind of like, “Hey jerks!” You came along behind me, and I’m grateful for it, too. I really like that we have shared experiences but as I get older, sometimes I want credit. I’m surprised to find the things I want credit for. I don’t necessarily want more career success but I want my brothers to acknowledge that they’ve copied me when we were younger, at least.

Here’s a short film profiling Will and Kevin, uploaded in 2012!

Well isn’t that always the way it is with pioneers? I knock the door down so you can follow me!

That’s right.

Take me back to that moment, then: What was it like for you in New York City and say 1998, early 1999?

I was a computer programmer at a five-person company and we did like consulting for big financial firms like Goldman Sachs. We would go into these companies and like, write little their intranet things, little utilities. The web was sort of new, still in the middle of the Silicon Alley boom, so there was lots of computer programming work. And I had lived in New York City for a couple of years, and I was quite lonely. I didn’t like know a lot of people in New York. I felt extremely behind. I didn’t have much of a life or direction. And I kind of aimlessly just started doing funny things. I started going to open mics, and telling jokes very timidly, auditing improv classes and I was honestly just like bored. I just wanted creative things in my life and I wasn’t like sure how to do it. So I kind of bumped around. I would look in The New York Press and the Village Voice and see what like shows were listed in the comedy section and just kind of try them, whether it was a stand-up show or some kind of weird Off-Broadway thing in the Lower East Side at the Collective Unconscious stage. That was the name of the stage down on Ludlow. I was doing stand-up, but when I took an improv class at the then brand new UCB Theater. I really enjoyed it. I really liked the whole group hug, you-are-important aspect of improv. And I felt like it was really like good for my personality. I felt like it was sort of like making me work an emotional muscle that had atrophied. The whole acting part of improv, speak to the most important thing, get to the heart of the matter, be affected, be vulnerable. It all felt like kind of good advice.

What was that impulse though in you that made you even seek out comedy? Boredom could have expressed itself in very different ways.

I love that question. My family had been funny. My mother, who I mentioned before, had died when I was 16. She was quite funny and her sisters, my aunts, like being funny was just so important to the way everybody communicated and weirdly like being obsessed with comedy culture. Like tracking who was on SNL, certainly, our family was not alone in that. But we were sort of an who’s on SNL this season family, and what is Steve Martin doing and, you know, do we like this Eddie Murphy special. My mom talking about stuff happening in the late 80s, was kind of part of the culture so then when I got a computer programming job, nobody was funny. Everybody was so dry and factual and efficient, that I just kind of missed it. So, I think I was looking for my family again a little bit and my younger brother, too, even though they were, they were a lot younger than me. By the time I was in my 20s, I would see them and be like yes these guys get it like they’re quirky and strange and Canadian. We have Canadian heritage. And so I culturally missed people who liked being funny as part of their identity. Again, I really think it was more of a social urge. Tt was missing my mom and her sisters. Think that drove me that way.

And it was the Upright Citizens Brigade that made you feel that sense of community and home.

Like the very first class I took…I started going to their shows, before they had a theater when they were doing things at this place called Solo Arts on 18th Street. And, you know, shows were being listed in the New York Press and I don’t remember how I heard about it but I was going to enough comedy shows that I would just sort of catch wind of other stuff so I was seeing UCB shows early. Actually what happened was somebody broke up with me I was dating somebody and she dumped me when I was 29 and I was like well, I need to keep myself busy, so I took an improv class at UCB to fill my time. And my first class was Monday night, taught by Kevin Mullaney, and after the very first class which was from 7-10, somebody was like let’s go to McManus, which ended up being like the sort of unofficial pub of the UCB, and we all went out and stayed out for like three hours. And that’s what hooked me just like, oh, people want to hang out and then like some people were like, Oh, we’re gonna go see a show. Thursday night or whatever and I was like I’ll be there and it was like, I mean I had nothing but time, so I just started going to the UCB always.

Who was your first UCB friend?

His name is Mitch Magee, I’m still friends with them, we’re friends in LA and we both live there. I just went for a walk with him a couple weeks ago.

Mitch was an early internet video guy.

Yes! I think he’s a brilliant director and he did a lot of really artsy weirdo. funny videos online, as part of the Channel 101 community in New York.

Channel 101: That was the thing that Dan Harmon did?

Dan Harmon and Rob Schrab started Channel 101 in LA. It’s like an institution and phenomenon where it’d be a monthly video series, and before YouTube rose to prominence, it was especially big, and then in New York we copied it, and did our own little bastard version of it. And Mitch was like kind of a king of that New York colony.

NOTE: Channel 101 even begat a TV series, albeit briefly for VH1, called Acceptable.TV in the spring of 2007. Executive produced by Jack Black, it ran for eight episodes from March to May of 2007. From Wikipedia’s synopsis: “Each show was composed of several mini-episodes created by the Acceptable.TV staff, with one mini-episode that was submitted by a viewer. After each episode viewers would be able to vote online for their two favorites. The two that received the most votes will be continued in the following episode, and the remaining three would be cancelled and replaced by new mini-shows.”

By the time I moved to New York City in 2007 and started attending comedy shows in person, you were already part of The Stepfathers.

Yeah, I probably had just joined.

What was your experience like for those first seven years, before joining The Stepfathers? Was it a slog, trying to get on a Harold team? Or was that early enough in the UCB that it wasn’t so difficult?

When I got on a Harold team pretty early, it wasn’t as hard when I got on as it would become. Although yes, so like I started classes in ‘99 and I got on a team at the end of 2000 which is pretty fast. And that speaks more to that there was less people there, rather than me being good.

The theater didn’t have a reputation yet.

Oh yeah, nobody was at shows. Like Harold Night was half full, at best. ASSSSCAT would sell out, but almost nothing else would. In my memory. And it was really hit or miss whether there’d be any crowd there, which stunned me because in those early days of ECB and I’m talking like 1999 2000 2001, you know there’d be like, I mean it was very hit or miss, you could go to the UCB and see a very amateurish show from someone who hadn’t done that much. You could also see like Tina Fey trying out stuff, This is before she was like, on camera, so she wasn’t like famous but she’d be introduced as the head writer of SNL. Even if you had never heard of her you’d be like Jesus, that’s a pretty good bonafide right there. Todd Barry I remember did a show that Matt Besser directed. These shows were five bucks or free, so you could go to Gotham Comedy Club and pay like $10 for a ticket and $8 each for two drinks to watch 10 stand-ups talk about how everything sucked, or you could pay $5 at UCB, roll the dice and more than half the time you’d see somebody incredible. To me was like this really amazing hidden kingdom.

I couldn’t believe that like it wasn’t more popular, I mean it would become more popular. But in these early days like nobody was there and I was stunned. I would bring like my normal friends my quote unquote normal from computer programming, friends from high school who visited, I’d be like, you’ve got to come to UCB, and half the time they’d be like, I didn’t like it. Their impression was affected by just how dingy the theater was sort of, like how unprofessional the box office was. And I’d be like, yeah, but it was like Adam McKay was doing probably like, Who’s Adam McKay? Like you know, he’s a writer for SNL and he’s funny, they’d be like well, I hated it.

He’s a future Oscar winner!

Yeah, nobody gave a shit and I was like, I think I’m right, I think this place is Motown, in 1961, in terms of like burgeoning talent that the nation had yet to discover. And I think I was right.

You were right. Well, that’s one of the things I loved you have this website. I had to dig around a little bit to get there. I had no idea that this existed or that you are part of it, you have up there a video that you shot of Amy Winehouse. It reminds me very much of what you were just saying about UCB before it became huge you’re shooting this video of Amy Winehouse at AOL. For those of you who aren’t that old, it used to be the internet company. You’re working at AOL, you’re shooting video of this young singer who you do not know.

I did not know her. Yeah, in January of 2006 or something like that. Yeah, I worked at AOL as a video producer, which really just meant…it was a really like menial job but really good experience like I had to just like, hold cameras and, you know coil up cables and then like, do sort of fussy file management things that required some technical knowhow but mostly just being comfortable learning stuff as you went in a sort of digital film environment. AOL Music was a department where they would have different artists come in and perform, and they would put the video on AOL and so Amy Winehouse is there but like she — her songs were not yet big in America, like I think they were about to be released, I definitely had never heard of her — and they were like go film this British girl, you know, we’re recording her audio for a podcast but we might as well grab some video. And so I went down there with a camera and I didn’t know how to work it. If I had set the exposure to auto and done the white balance correctly that video would be so much better quality, but I didn’t know. I just pointed the camera at her, hit record, she opened up her mouth and started singing and I was like, Oh My, Who is this? This person’s incredible! They released the video then like I think like four months later she was like a huge star in America. I mean I met her, technically. You know dumb I was, she finished two of songs I put the camera down I was like oh my god you’re great! She was like, thanks love. What an idiot I sounded like. I think she knew she was great. She didn’t need Will Hines telling her she was great. I was just so blown away, it just fell out of my mouth.

Right. But actually she did need to hear it. Because just like you and your friends at the UCB, you needed people to understand the greatness that was there.

I think so. We didn’t meet Beyonce, but I was in the room with Beyonce when she sang stuff, and it was really fun, there’s a lot of cool folks that came through there.

But, but just like that a lot of cool folks came through UCB. What was it like from your perspective to to see people come in alongside you, who were, who nobody knew and then see them become superstars?

I mean it’s, it’s mostly exciting. What that question reminds me of is, you know, I would see friends of mine who I thought were amazing. They would do stuff in obscurity for a while and then sort of explode. It felt validating. It felt like, oh, we were right, this person is great. You know, The Stepfathers the team you mentioned that I got on in 2007, Zach Wood and Bobby Moynihan were on that team when I joined. Bobby got SNL, pretty much a year after that, I think. And Zach started doing stuff on The Office not too long after that, and then became a lot more famous. And it was validating because we knew that Bobby and Zach were terrific. We knew they were great so when Hollywood caught up, it just feels like oh yeah, we’re not idiots. We have good taste in people. It was like I was a bass player in a lot of great bands, you know, and so the lead singers would go and be famous. I’d be like: Yeah, I played bass for that guy. I kind of feel like a comedy session musician in a lot of ways,

Comedy session. Not the Paul McCartney. As a Beatles guy, I would’ve thought you’d consider yourself the Paul McCartney, go, I’m the Paul.

I can’t imagine having enough self-esteem to be like I see myself as the Paul McCartney in this group. I think I’m as valuable to this group as Paul McCartney was to The Beatles? I can’t imagine.

I spoke with Chris Gethard. Last time I spoke with him way back when he did that movie, Mike Birbiglia’s Don’t Think Twice. Which kind of deals with this concept of, you’re on a team and then you see people become stars in front of your eyes.

I love Birbiglia and I think he’s genius, and I love that he made that movie. There are certain aspects of improv he caught well but I don’t think that the fame jealousy was accurate to me. To me the premise of Don’t Think Twice is what a stand-up comedian thinks the improv world is like. Everybody is just jealous of each other, because I was on teams — that movie is about an improv team where somebody gets on SNL and becomes famous, and it like rips the team apart — but I was on The Stepfathers, Bobby Moynihan got SNL, we were incredibly psyched for Bobby. It meant we were good. We all gathered around and watched his first show and we were thrilled. That really never changed. I still get excited when I see my friends to do stuff. I mean I have jealousy and insecurities also but they’re not shaped like, I feel weirdly soothed when friends of mine get famous. I’m like oh, maybe I’ll get something. I’m standing right next this guy. Sometimes I have gotten some success. Also my expectations for myself were so low, like, when I started doing improv, it was beyond me that I would even be able to be good in a class. So, that I was able to hold people’s attention on a stage, you know, I was playing with house money already by the time Bobby got SNL.

Are you still dealing with any sort of self esteem issues?

Still. Yeah, I definitely have had confidence issues, and I still do. I mean I have a weird combination of confidence issues but also a willingness to just fling myself into situations that I don’t feel prepared for. So I sort of have audacity and confidence issues. This is gonna fail but I will do it anyway, It’s maybe a weird combination that I possess.

So how did you talk yourself into eventually making the move to LA?

It was all just later than you should do it, right? Like I moved to LA when I was 43. You know, I basically started becoming a professional actor when I was 43. That’s not really the ideal age to go to Hollywood, you know. That’s not the vision, that’s not the biography that people picture for themselves when they imagine hitting it big in Hollywood, you know, they’re like, well, I’ll wait till I’m 43 to move there. I started taking improv classes when I was 29, first started writing sketch shows when I was in my mid 30s. I always felt extremely old relative to the very young culture at UCB, so I had to wrestle with always feeling behind, which I then realized that everybody feels behind. Even the 25 year olds! They feel behind, they feel late, which is crazy but they do. Like they look at like Lena Dunham or I don’t know, you know someone who’s like making it. They just announced new SNL writers and three of them are a sketch team they’re in their early 20s And they’re writing for SNL! I mean I know two of them are children of SNL. But also they also are good, and if you’re 26 and you’re doing sketch in New York City, you look at them and you are behind. So I kind of realized that even though I felt behind and I was behind, that nursing that insecurity was pointless. I also realized that one of the keys is just to outlast everybody. Just like don’t quit, ever. So many people quit. Like your greatest competition will just give up if you wait a year. You know I remember people in 2000 at UCB taking classes and being like, well, when do I get something? Those people all left.

Here you are 20 years later.

Yeah, just wait another 20 years, baby. And you’ll do a half hour stand-up set on that very stage. I just started pursuing stand up like two years ago in LA, really just to try to get cast more. I was like, I think if I’m onstage in front of more people I’ll get cast. If I can like present my persona to more and more crowds.

Wow, even, even though you already had a recurring character on a network sitcom in Brooklyn Nine Nine.

Well, yeah, because like that character really, he’s got four appearances over seven years. That’s not really recurring right? I don’t support myself with acting money. There have been a couple of years where I have but mostly I don’t. So, I feel funnier than the prominence of my acting career, so it’s like well, maybe if I show people what I think my energy is they’ll put me in stuff. I think most people to get into stand-up to be like writers and, you know joke writers. I’m not a good enough joke writer, I’m too lazy, but I kind of use, stand-up to present my personality. I do write jokes and do bits. But I don’t think anybody would watch my stand-up and be like hire that guy to be a writer, but they might be like, hire that guy to be the sad teacher in our sitcom.

Although you’d do a great job as that sad teacher.

Yeah, I’m down for it.

But as you told me, just earlier in this podcast, it’s not as if when you started taking classes and going open mics, you did it with any grand ambitions. You were just bored with life as a computer programmer. You weren’t going into it like those kids who do the Harvard Lampoon and they’re like, I’m getting into the Harvard Lampoon and then I’m gonna get on The Simpsons and then I’m gonna do this by the time I’m 26.

I kind of wish I had. I would’ve done better professionally. Yeah, I didn’t have the vision of what that life would be like. When I was 28, and I was doing open mics in New York, not for too long, not too many, but a little bit, if you were like, ‘Hey do you want to be on television?’ I would have been like, How does that happen? I don’t even see how that happens. And if you can’t like visualize that it’s hard to do it. Does somebody come to an open mic and cast you? Like how does it even occur? 10 years later I’d be like, oh, you have to like do a lot of comedy and then you have a lot of friends and then one of them become successful and they recommend you and then you get to submit and that’s how it happens. So you have to like make 100 friends who are all trying to do it, but I didn’t know that. Even when I started UCB, it was just like, I was just interested in like healing myself emotionally. I mean it’s kind of boring and emo, but like my inner like struggle is like an emotional journey not like a professional one. Basically, I was super shy unconfident kid my mother died, my dad kind of retreated into a corner and stayed quietly drunk for 15 years, sweet guy but like not engaged. Me and my brothers were just sort of bored and alone, and doing everything after that was just trying to heal myself, just trying to make connections and be happy and be present. My mother died when she was 40, so I was like maybe I don’t how long am I gonna live? When I was 30 and I started doing stand up, I was like maybe I’ll be dead in 10 years like her, you know, maybe I’ll get cancer when I’m 37 and that’s it. So do I want to be in a cubicle? It was like, I want to be happy today. And if I walked into the UCB in level one, took that class and then we went to McManus. Today was, what a great day! Gotta have more days like this. And then within that I’d be like, Oh, I want to have a better time when I’m in class, how can I get better at class? And then I got put on a team and I’d be like, Oh, I’d like to be better on this team. How do I get better on this team? Maybe I’ll do this maybe I’ll take this acting class maybe I’ll go watch the show. And so I wasn’t ever really good at looking forward. I didn’t know how to visualize next steps. I really still maybe don’t too much.

Well, that leads me leads me into asking you about the book, because your improv book, How to be The greatest Improviser on Earth, started as a Tumblr. So when he started the Tumblr. Were you thinking at that point about?

No. I started the Tumblr because I was working for the UCB, running the school, sitting in the office, and I would hear people say opinions about improv in my classes or in the office and I would disagree with them and I wanted to argue with them. So I started an improv blog to express my opinions, because it felt like the polite way to do that. Like that way people could read them if they wanted, or ignore them, I wasn’t like obnoxiously being like, listen to me. And then it got popular. I got like 20,000 people subscribed to it. Way more than I ever thought would happen, at its peak, and then I started paying more attention to it. Then I saw the numbers start to drop a lot. And, you know, based on like how many people were liking it. And I was like, you know, this blog’s on the way out. I’m gonna make a book to make the good parts permanent. And so then I started doing that. Also I had just moved to LA and I was, I had all kinds of time in my hands, because it was the first time of my life I didn’t have a full time job. So I just had time. And I did that to keep busy.

And now you have the book. And the book stands in a dialogue with the UCB book, right?

People see it that way. The book is actually pretty unfocused. I really do like my book and there’s things in the book I like a lot, but there is no grand thesis of my book. People are like what’s it about? I’m like I don’t know, it’s a hodgepodge of advice about doing improv. I think my book is pretty successful within the tiny tiny world of improv books, and I say that that is 75% because of the title, how to be the greatest improviser on earth. If you’re going to write a book, Sean. Are you going to write a book? Make sure that title is salty. Well that’s my advice, because people buy books because they identify with it, they don’t buy them to read them. They buy it because they’re like this book is me.

Well, since you stopped doing the podcast, I Will Write Your Book, I appreciate this advice.

Man, you really know your stuff, I appreciate it.

You spoke a little bit about like the inner dialogue with yourself. And it reminds me that that’s kind of like the workshop that you’re giving while you’re in town this weekend, right, there’s the fool and there’s the voice of reason.

Yeah, fool vs. voice of reason. It’s an improv workshop and it’s about the two roles that you can play when you’re doing improv scenes. You’re either like a fool who’s doing something foolish and funny, or you’re a voice of aeason who is saying that the fool is foolish. You’re either the emperor who wears no clothes or the kid who says hey you don’t have any clothes on. And it’s like, being comfortable with both of those jobs.

How do you feel about about those voices in your head when you’re offstage?

I think it applies to real life. I think you have to be willing to be a fool sometimes and you have to be willing to be a voice of reason and not let either one of them rule too much. If your voice of reason rules too much, you’ll never do anything. And if the fool rules too much, then you’re drunk at 4 a.m. starting a fight with a barber.

Well thank you Will Hines for not being drunk at 4 a.m. but instead, doing a podcast with me early on a Saturday morning, which is what grown men from Generation X do when they become grown men.

Weren’t we supposed to be the ones, Generation X, we were supposed to like fix the Baby Boomers’ problems? The Baby Boomers were like all on drugs and divorced and we were supposed to grow up and like be practical. I remember that was like one of the ways that there was like a lot of, this is what we are generally, in the early 90s I remember being like, we’re not show offs like the baby boomers, we’re gonna get our hands dirty and solve problems. Now I guess we’re just out of touch idiots, but when we were young, that was that was gonna be the identity of Gen X.

I kind of feel like we were both the fools and the voice of reason because we were telling the baby boomers that they had no clothes, but we also weren’t doing anything about it.

Yeah, yeah. But we wanted to.

But that’s why they called us slackers because we didn’t.

That’s right, we were slackers. Yeah, we dropped out. That was our protest, you know, we weren’t gonna play the game that everybody else played…

And see how well that turned out?!

Everything worked! That’s what I remember, everything got better. We fixed everything, everything is great now. Yeah, no problems.