Brian Kiley
written by Ken Carlson
“When I approach a joke (for Conan),” says Brian Kiley, comedian and writer for Late Night with Conan O’Brien, “I try and see who the target is going to be. For instance, if the premise is about Hillary Clinton, chances are the punch line will be a Bill Clinton joke. I also try to make sure that it’s a light enough topic. Something too heavy is going to bum out the audience. I also look at a premise from different angles until I can come up with something that makes me laugh. (it doesn’t always happen). One thing I’ve learned as a comic is the type of joke people want to hear from me. A joke that may work perfectly for another comic may be too graphic, too mean or too politically slanted for me and may not fit my stage persona. It’s the same with writing jokes for Conan. Jokes that might be perfect for Chris Rock may not work for Conan. Who is telling the joke means as much as the joke itself.”
In a play, whether it’s a Broadway spectacular a black box one act in the back room of a dingy bar; if you take a peak behind the curtain just before showtime, you get some sense of what goes into putting it together. Dancers are running around looking for costumes, lead actors are screaming for their agents, producers are yelling at directors, and directors are desperate for a drink. But the connection to what’s been typed on paper for all to hear is kind of distant, with its related decisions, one hopes, being made in the reasonably distant past.
In the world of late night television, that connection to the writers is much more immediate, with input and cajoling for monologues carrying on almost until the band plays the opening theme song. One of those writers, as solid as bedrock for this industry, is comedian Brian Kiley.
For fifteen years, Kiley has written for Late Night with Conan O’Brien, the plucky, offbeat contender that many didn’t give a chance. Before that, this quiet husband and dad was performing stand-up in Boston, a practice that he has stayed loyal to with a quiet, almost innocent delivery and smart humor that has the respect from the leaders in the business.
“My favorite Kiley joke.” says comedian Jonathan Katz, “I got a house with one and a half bathrooms which is great because sometimes you just wanna wash your legs.”
“It started when I was in college,” says Kiley, a native of Newton, Mass. “As a kid, I wanted to be like Rob Petry on the Dick VanDyke Show. And I wanted to be a comedian, but as a kid, you wonder, how do you become a comedian? Well, there’s no way I could do that, so I’ll be a comedy writer. I wanted to be like Rob Petry, write comedy and marry Mary Tyler Moore. That part has changed the last couple of years.”
“I saw a show when I was at BC. It was a hosted by a comedian named Barry Crimmons,” says Kiley. “He was really funny. It was at a room called Ding Ho. I talked to him and told him I wanted to make a living writing comedy. He said Boston was too small a place to make a living doing that, so I should come down and perform. I remember thinking, ‘Oh, I could never do that! But I took a comedy writing class later that summer at Emerson, taught by Denis Leary. For the last class I did some stand-up, which was kind of a show. There was a woman comic there, Andrea Michaels. She said I should pursue it. So, I went to an open mic and Barry was the host. It was coincidental. He gave me a good spot, a great intro, and it went great! I bombed the next week. I did a whole new set at 1 in the morning. It was torture.”
“I didn’t do it very much in college, but did it a lot while I was working full time. Once I got out of college, I decided to see if I could do it. I lived at home for a couple of years. I moved out when I was 24. But I’ve been making my living at comedy ever since. I hit the comedy boom in the right way. I lucked out and haven’t had to have a real job.”
One of the breakthrough moments for any comedy writer is the first time they hear someone else performing their jokes. For Kiley, that time came from when someone who could not be any more different from him gave him a chance. “When I bombed for the first time at the Ding Ho,” Kiley recalls. “Lenny Clarke was the host. The next time I came in, I couldn’t get on the list because it was full, but Lenny came over and said, ‘Fuck it. You got fucked last week!’ So he put me up and gave me a good spot and it went great. In the old days, if I bombed, I would invariably make a joke about it. So I started incorporating those lines into my act. People used to ask me, ‘Why are you joking about bombing so much?’ It was because I was so used to doing them it became part of my act. But they said I was having a good set!”
“Lenny got a show, Sunday Comics, on FOX. This was around seventeen years ago. I sent in a couple of jokes there. He did them. He knew me and it was fun to see him do it. This was before email, so I guess I faxed them to him, now that I think about it. It seems like such a primitive time. It’s funny how things change so quickly. They would say they wanted jokes about what was going on in the news. They wanted high school jokes, or whatever the theme was. I didn’t want to give them too many evergreen jokes because if they were good, I wanted to do them. But with topical jokes, sure. The first joke was about Yugoslavia. It was breaking up. Who would’ve thought the country that brought us the Yugo was falling apart?”
“It was a neat thing,” Kiley describes, “the novelty of it. But I was still doing stand-up and didn’t want to give jokes away for fifty bucks if I could use them hundreds of times. But they were very encouraging – You’re really good at writing topical jokes! When I got the job here, I was doing a lot of topical stuff in my act. The thing about topical stuff, you can generate a lot of it. But also, it has a short shelf life, so you have to keep generating it. Tom Agna, a friend of mine here recommended me when someone got fired. I basically typed up half my act and sent it in. Conan said, ‘OK, you can start tomorrow.’”
“The show was kind of shaky then,” says Kiley. “It was new. People didn’t think it was going to last. When I started coming into work, there would be stories in the Post or Daily News every day that it was going off the air. I thought, it would OK to do for thirteen weeks, maybe six months. I’ll put away some money and have that experience. But I had thirteen week contracts for years. I even commuted back and forth between here and Boston for a few years. My wife had this great job with PriceWaterhouse. Then she became a VP for a company. They let me work from home one or two days a week. So I went back and forth. It’s funny, when you write for somebody else, as opposed to performing it yourself, the highs aren’t as high and the lows aren’t as low. If he kills, I’m happy but not elated. If he eats it, it’s not as devastating. The vicarious thing is not the same as doing it yourself.”
Naturally, the process for getting something he dreams up to be accepted by an audience with laughs is different for Brian the writer as opposed to a comic, but the number of layers or parties involved, considering the size and what’s at stake, are remarkably small. There are a couple of hurdles he has to clear. First, he has to get Conan’s approval. Then Conan might do a joke and the crowd won’t like it. “You think, ‘Oh, huh,’” says Kiley. “I like that joke. Conan liked it. I thought it was all set but the crowd said no. Other times I like a joke and Conan doesn’t, so I never get the chance to see if the crowd will like it. But, I’m fortunate because I respect his judgement. Maybe once a week, I write a joke that I love and I’m fortunate he will invariably pick that one. I think we’re on the same page for the most part.”
“During the Writer’s Strike, I was fortunate that I could go out and do stand-up,” says Kiley. “At this point, I’m pretty selective about my gigs. But then, I had to take everything. So I was driving three hours to a terrible gig for terrible money, driving home at 3 a.m. and thinking, ‘Wow, I haven’t done this for years. I don’t miss this at all. So, you take some beatings.’ Generally I work nice places now. Just relying on stand-up is hard. I headlined for a week in Ann Arbor. I flew out to do the shows. I finished my gig at midnight and hey called me at 4:30 or 5 a.m. to go do some radio show. They picked me up at 5:30 and there was a snowstorm. So, they brought me back to the hotel and I went back to bed. It became a phone interview at 9 instead. It’s a demanding schedule. You forget how hard it is fulltime. You have that pressure because it has to go well and not have anything to fall back on.”
“[The strike] was emotional for some more than others,” says Kiley about his team at Late Night, “Some people were very upset about it. Being able to do stand-up allowed me to go out and be a productive member of society. We had picket duty. It was kind of neat actually. I got to meet some interesting people there, like the guy who wrote Little Miss Sunshine and writers from MONK and Law & Order on the picket lines. Generally, writers are in their own little bubble and you don’t cross paths. I also got to spend more time with the kids, but had to cut back on some things, couldn’t take trips we had planned to do. Being out of work is not great.”
“I use Brian as an example in a lot of my classes,” says Eddie Brill from The Late Show with David Letterman. “Brian was always a great writer. His material has always been stellar. But it took him a while to become the great performer he is. I remember him delivering this great smart and silly material but sweating profusely and so wrought with stage fright. But with tons of stage time, his stage presence ended up matching his writing. He is one of the few comics to appear on Letterman, Conan and Leno!”
At a time when comedians seem to be getting louder and more crass, perpetuating the image of the foul-mouthed malcontent, shouting down everyone in their path, Kiley seems to cruise on by at his own pace and volume. “Crowds get a sense when someone’s not being genuine,” says Kiley. “If I went up and did that (shouting and cursing) I don’t think they’d buy it. ‘What are you doing?’ The audience has an innate sense when people are being who they are or not. I think performers look to have a unique character or persona in comedy. Really, if you’re just yourself, that’s your comedic character. I remember years ago, I took a class and there was an average looking guy named Joe Smith. I was fascinated by him. He was the most average guy I met in my life. I was riveted. As long as you are yourself in comedy it takes a while at the beginning to develop comedy to fit yourself. The way you perceive yourself is not the way other people perceive you to be. I would do offbeat, Steven Wright-ish jokes when I first started out and the audience would look at me, ‘No, that didn’t happen to you.’ Over time, you end up crafting your character. The audience has to buy the premise coming from you. I think if your comedy fits you and your character, and you get more experience, your act gets stronger and it works for everybody. You have to tap into yourself.”
Behind the scenes at 30 Rockefeller Center, the glamor of network entertainment is less evident than you might think. The corporate labyrinth of the everyday workplace, with its cubes and offices and darkened studios must be expertly traversed to find your way around. Much like many comedy clubs, where the green room might describe something growing on the carpet, what the audience doesn’t see, is functional, not fancy. It is between those two settings; one in the spotlight and one off camera, where Kiley has made his living and appreciates that fact. “There was the comedy boom of the 80’s. That’s gone,” says Kiley. “There’s not as much work as there used to be. There are fewer clubs. There used to be a lot of one-nighters. On the writing side, there used to be forty sitcoms on the air. Now there are maybe five. That’s a lot of comedy writers out of work. This is a tough time for sitcom writers. I hope it’s not over. I hope it revives. I don’t have a lot of things I like to TIVO every week, but I don’t want sitcoms to go away either. I hope The Office and 30 Rock can hang in there and others spring back up.”
“It’s a good environment here,” says Kiley on his fifteen years with the program. “I like Conan a lot. He’s a hilarious guy. If you have a boss who is a nightmare, it makes it a lot tougher. If you have a wife and kids, you’re less likely to see what’s out there. Usually there’s nothing. The guy I share my office with has been here since the beginning. There are probably five of six of the writers that have been here at least 10 to 12 years. I’m amazed when an amazingly talented person will leave; like Allison Silverman left to be the head writer on ‘Colbert’, Jonathan Blitz to do other things, Louis CK left; all these funny people. Somehow the network finds another funny person to breathe new life into the show. It’s been amazing how, they just go into the farm system and bring someone in that’s great!”
“Everybody’s feeling the money pinch with the economy being bad,” Kiley admits. “It’s a drag to see fewer gigs. A comic friend of mine died, Bob Lazarus. There were a lot of comedians there, funny people, who said there wasn’t much work out there. We shouldn’t be home on weekends, especially some of these funny guys who have been out there for twenty-five years. You have to do a lot of shows to stay sharp. I do one or two shows a week and shows during the weekend. You have to stay sharp or else it’s bad. It’s not good for you, not good for the audience.”
“He is always someone we can count on to do a set for us last minute,” says Eddie Brill and has become one of Dave’s (Letterman) favorites. Also I admire that Brian had one of his jokes be the thread in a Sunday NY Times crossword puzzle. ‘If you’re scared to die...you better...not be scared to live!’”
“I get up and read through about five newspapers every morning,” says Kiley. “You skip through all the bad stuff. Conan’s not going to do jokes about that anyway. It keep me in a state of bliss. Sometimes I’ll come home and my wife will say, ‘Wasn’t that plane crash awful?’ ‘What plane crash?’ It was on the front page! But your mind blocks it out after a while. What’s Paris Hilton up to? It’s almost like being a child.”
“We go online to cnn.com,” Kiley continues, “and look online, etc and meet with the other writers. Then I’ll brainstorm with another guy. We compile our stuff, and a joke will spark an idea about something else. In the end we come up with forty to fifty jokes. There’s a little rehearsal with Conan; the interns and camera guys act as the crowd. We meet with him for half an hour before he goes on to pick the order. Some days we have better than others. Some days there’s a guest he can’t wait to talk to. Some days, it’ll be, ‘Oh no, not that guy.’ That can be a factor in his head. But he’s usually getting his on-air persona ready. In the old days when Andy was here, the two of them would be fooling around. To me it was two guys warming up and it was hilarious. That’s always one of my favorite parts of the day. It will be us, the cue card guys. That meeting; making Conan laugh feels good. We have to generate so much stuff. You learn very quickly that you can’t say, ‘You can’t change MY joke. That’s MY joke.’ You forget whose was whose. We don’t have that luxury.”
“Brian,” says Jonathan Katz, “is the only comedian to give me a joke: ‘My uncle died penniless, had a lot of dimes though.’ He is brilliant and prolific, I think it is the prolific thing that sets him apart. He is one of the most quotable comedians out there. He is the only non Jew in the big book of Jewish humor.
For more on Brian, visit BrianKiley.com