Greg Fitzsimmons

By Ben Kharakh

(Picture of Greg Fitzsimmons)

This interview first appeared online on on October 27th, 2006

Greg Fitzsimmons has been on Conan, Letterman, and Leno, has two Comedy Central Presents Specials, appears regularly on VH1, won the Jury Award for Best Comedian at the 2001 Aspen Comedy Festival, has two Daytime Emmy for writing and producing The Ellen DeGeneres Show, and is currently a writer for HBO's Lucky Louie.

When did you develop an interest in comedy?

As a small kid I collected and memorized comedy albums. My dad was a Radio announcer in NY. He would have me on the show and I would do the routines.

What were you like in school?

Full class clown. Bored with the work and restless. Would disrupt a lot. Teachers mostly liked me though. The bad ones hated me.

Is school something that you enjoyed and why?

I liked being around all the other kids, but I felt trapped. Like life was going on outside and I was missing it.

What sort of aspirations did you have as a child?

I read a lot of books and wanted to be a writer. Someone who lived a lot of adventures and then wrote about it.

Is television something that impacted you greatly growing up?

Johnny Carson and, believe it or not, Bob Hope at a young age. Then when Steve Martin did his one-hour specials once in a while. Crazy sketches. Police Squad, which was the precursor to the Naked Gun series.

Did you ever do any talent shows at your school?

Senior year of high school I did standup at the talent show. I was doing jokes about how the Western Civilizations teacher and the art teacher were sleeping together in secret. They would always sign up for school trip chaperones together. The principal unplugged my microphone so I shouted the rest of it out.

Did you do any writing, such as short stories or sketches?

When I was about eight, I wrote a screenplay for a children's James Bond movie. It is still in turnaround.

Were you incorporating humor into your daily routine in school and college?

In high school and college, I always wrote papers that were funny. Teachers loved it because it was a break for them. Even if the papers were not as strong, I could usually snake a decent grade because they were fun to read. There were several teachers who I respected a lot who encouraged me to become a comedian or a comedy writer.

What did you study in college?

English major.

Were you in some sort of comedy troupe in college?

Senior year I joined an Improvisational Comedy Troupe. We did a lot of shows on campus and in local clubs. We had a regular Wednesday night show at a Greek restaurant in Cambridge where they didn't speak much English. They paid us in food.

When did you decide to do standup?

Officially, my senior year. But my whole life it is what I wanted to do. In high school I would spend a lot of time in the comedy clubs in New York City watching guys like Seinfeld, Paul Reiser, and others on their way up.

When was the first time that you performed?

Besides the high school talent show, freshman year at college, Boston U, I went on the night of the Superbowl. The Patys had gotten their asses kicked by the Bears and the crowd was drunk.

How did that go?

Went well, mostly because I had so many friends in the audience supporting me.

How has your material changed over time?

Same act. Just more confident now.(Just kidding). I have grown away from pure jokes about funny concepts and more about my life. I tell stories laced with jokes now. I like to talk about things that might make me uncomfortable to share. Then I know it is real and means something to me. Once I have done it on stage, I feel less ashamed about things.

How many open mics were you doing at the time?

Boston was at the height of the comedy boom in the late 80's. I started out just doing open mikes in town. There were maybe a half a dozen places you could sign up and try to get on. Then you'd get invited to do other rooms usually run by other comics. Finally, you 'd get a paid gig, maybe $10, just outside the city.

How much time would you dedicate to writing everyday?

I would like to say a lot. But at the time I wasn't that disciplined. I write more now. But more than average I would say. Not regularly. Sometimes I would get together with other comics and we would write together. Come up with a topic and then each write jokes about it.

How many times do you perform a particular bit before you're confident with it?

It's always exciting when you have a new bit that works. But it can take weeks or months before it really works. I have one bit that I worked on for years and never really got it right. Someday.

What do you think of standup courses?

Waste of time. Go hang out at clubs. See what comics are doing. Why do you like it or not like it. Do it. Over and over and over.

Have you taken any Improv courses?

We used to take the money we made on our gigs in the Improv troupe and hire this woman to coach us.

How long was it before you moved up to middling or emceeing?

After I started it was about 6 months before I got emcee gigs and then after that about a year and a half to middle.

Is emceeing something that you enjoyed doing?

Yes. I still emcee shows, like benefits. You are really the most important one on the show and you control the crowd.

How much improvisation do you incorporate into your performances?

A lot on a good night. Little on a bad night. So sometimes if a set isn't going well, I reach out to the crowd and try to get something going. It can backfire, but it gets you out of your head. Improv really helps you in standup because most comics will see the crowd as a threat and attack them, but if your instincts are to incorporate them into what you are doing, they love it and you can take it a lot farther than just shitting on a guy.

What were the next several years like for you?

I started splitting my time between NY and Boston, driving back and forth every week so I could make a living at the Boston clubs and work my way into NY at the same time. Finally, I moved to NY and did a two year acting program at The Neighborhood Playhouse while going on the road on the weekends. I was headlining at this point and doing colleges all over the country.

What changes have you noticed in comedy since you've gotten involved?

There are two schools of comics: those that are more esoteric and nerdy doing alternative rooms in town and the road comics who are increasingly less original.

What are some misconceptions about standup that you'd like to clear up?

It ain't magic. It takes hard work and craft to make it work. Funny people don't always make it. You need to handle your career wisely and be aggressive sometimes. Success doesn't just come to you.

What are some current trends in comedy you'd like to comment on?

Late night TV and touring used to be the way people made a name for themselves and started drawing in the clubs. Now the Internet seems to be becoming much more powerful. That and Last Comic Standing. Neither of these things really promote good comedy; it's just massive marketing. My fear is the recent upswing in standups popularity is going to start to backfire again as crowds go see someone headline who didn't really get there from being a great club comic, but rather from shrewd marketing or TV exposure.

What quality do you think someone should posses if their interested in getting involved in standup comedy?

There's no one-answer except tenacity and a sense of humor. You have to be patient and you have to be doing it for the right reason. The right reason is to become a good comedian, not famous.

I often hear people say, "I want to move to LA to do comedy." When do you think that someone should make such a move, if they should make such a move at all?

Wait until Hollywood invites you. Very simple. And if you are good, they will.

What sort of venues do you prefer to perform in?

Independently owned and operated comedy clubs.

How do you feel about college shows?

Love them. College kids want to laugh and they have a lot of energy. It used to be that you had to be squeaky clean at a college, but now mostly they let you do whatever you want.

Are you noticing that comedian is a career young people aspire to have?

Yes. I hope they want to bring something new to it, because it's not just a showcase for sitcoms or a way to get laid. Although, it can lead to both.

Magazine-wise, why do you think that comedy doesn't get the same sort of attention as music, gardening, or cigars?

Even I don't want to hear a comedian talk about comedy. It's hard enough for me to be writing all this crap. I can't imagine having to read it.

What projects are you involved in?

I write for a new HBO comedy called, "Lucky Louie". It will premier June 11 after "Entourage". I also appear every week on "Best Week Ever" on VH1. I just did my second half hour special on Comedy Central and continue to tour clubs and colleges.

What projects are you contemplating?

None. I'm too busty too contemplate.

Do you have a special message to leave our readers with?

The only dirty comedy is comedy that is mean to people who have not made a choice to be the way they are. Everything else is fair game.

Visit for audio samples, articles written by Greg, tour dates, and to buy his album, Fitz of laughter.

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