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Comedians on Comedians: The Middle with Greg Fitzsimmons

Greg Fitzsimmons has won four Emmy Awards, has his own show on Sirius/XM, and has over 50 TV appearances. He’s a regular on Howard Stern, Letterman, Conan, and seemingly everything that’s ever aired on VH1. His podcast is wildly successful, his book “Dear Mrs. Fitzsimmons” did incredibly well, and he’s about to host a new series on the Speed Channel called “Pumped.” But all that and he’s not a household name.

“I have made it to the middle in show business and I really like it here,” Fitzsimmons said. “I’m not sure that more money or fame would bring me more happiness.”

Fitzsimmons’ happiness comes in part from the career he spent so many years building up. Growing up “obsessed” with standup, his first appearance was at a talent show his senior year of high school.

“There were drugs involved that night,” Fitzsimmons remembered about his routine bashing the faculty. “The principal unplugged my microphone half way through.”

After the standard demeaning rise (“I once had a woman vomit on me after I followed a comedian dressed up as a clam,” Fitzsimmons said.), Fitzsimmons landed a gig hosting Idiot Savants, a game show on MTV that lasted from December 1996 til April 1997.

But that same year, Fitzsimmons landed a sitcom deal, a show on the USA Network, and a number of other TV appearances. The next decade and a half was a steady climb, much of it centered around his long-term relationship with The Howard Stern Show.

“Stern is like required listening for everybody in show business,” Fitzsimmons said about the man who gave him his own show. “You cannot explain how someone gets as successful as him, but being near it gives you a confidence that you should go out and do it your own way.”

The other part of Fitzsimmons’ happiness comes from his family. Fitzsimmons even sent his mother his first Emmy.

“I think she has dinner with it every night,” Fitzsimmons said.

But it was Fitzsimmons’ father, radio personality Bob Fitzsimmons, that gave him the advice that would help shape him.

“My father told me when I first started that standup is exciting and I should pursue it, but that writing would be the thing that would give me power over my career,” Fitzsimmons said. “I never have to take a road gig or a writing gig I don’t want because I always have the ability to play one against the other.”

Fitzsimmons standup also reflects his writing ability. Much of his set is made up of short and to-the-point perfectly structured jokes.

“I’m not saying was intense at the screening,” Fitzsimmons set up during one of his Letterman appearances. “But tomorrow night the guy who frisked me is introducing me to his parents.”

Writing for shows like “Ellen” and the Emmy Awards themselves also allow Fitzsimmons to spend time at home with his wife and kids. And to obtain a kind of happiness we all seek.

“Irish parents will try to off-set their low self-esteem by producing successful children so nobody can look down on them,” Fitzsimmons only half joked. “My dad was really proud of me. It was a nice thing.”

While many stand-ups fill their lives with regret and a desperate desire to achieve whatever is next, Fitzsimmons is content with his “middle.” Well, almost content.

“I make a great living doing exactly what I want and have a lot of choices at any given time,” Fitzsimmons said. “I would, at some point however, like to do blow in a Porsche with Paulie Shore.”

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