Greg Fitzsimmons to Film Special at Music Hall

Once the pressure to ask funny questions soon wore off, I enjoyed a nice phone chat the other day with comedian Greg Fitzsimmons.

Fitzsimmons, born and raised in Tarrytown, is now raising his family in Los Angeles. His son surfs and plays soccer and his daughter skateboards. My talk with was him was famously sandwiched between his morning podcast interview with Judd Apatow and Adam Carolla’s podcast later that day. The next day, he would shoot his pilot show – a game show of comedians playing poker and betting with funny stories, for which he will play host.

Finally at the end of the week on Friday Fitzsimmons returns to film his first televised comedy special in two evening shows at the . He’s been honing his material across the country and has it down to a tight –and funny, we hope – hour (with maybe 10 minutes of bonus material).

What makes the Music Hall so special – or perhaps for him, unnerving – is all the old friends and relatives that will be the audience.

His mom still lives in town, his sister in Cortlandt, and his brother in the city. He expects his aunt and uncle to be in the audience.

“Sometimes my material is a little raw for [my family], a little too honest,” Fitzsimmons said. “But I try to keep them out of my head. It breaks a little with the Irish tradition of shrouding it all in secrecy and denial.”

All self-consciousness aside, the predominant feeling he said his family has in him is pride, which “means a lot to me. It’s the most primal instinct to have your parents’ approval.”

Fitzsimmons' dad passed away 20 years ago, but “he’ll be there" at the Music Hall, he said. He described his father as a “big radio guy in the city” who used to write jokes for his son. The first time Fitzsimmons did the Letterman show, “I said, here I go Dad.”

When it comes to comedians, picking on anyone and everyone is expected, but I believe we adore those most who make fun of themselves. Fitzsimmons calls his act a “snapshot of a middle-aged man with a receding hairline and a Prius.”

When asked about his upbringing here, he described a more free-range kind of childhood than is in style these days. His parents stayed out drinking until 3:30 or 4 a.m., so late that his former babysitter just reminded him on Facebook how she had to quit.

Fitzsimmons still has the best buddies here he grew up with. John Korzelius, now Sleepy Hollow Fire Chief, who he fondly refers to as “Johnny Trouble” and a “lunatic, who has no business having any kind of power.”

And Kyle McGovern, now Judge of Tarrytown, who he said, was “always a model child, of course.”

Sleepy Hollow Police Chief Gregory Camp has a signed copy of his book, Dear Mrs. Fitzsimmons: Tales of Redemption from an Irish Mailbox, on his office wall.

With local friends in such positions, Fitzsimmons said if he returned now his home would always be fire-free and his parking tickets dropped.

Complete with Prius, Fitzsimmons said he's gone "good" now, but back in the day he "spent some time in the North Tarrytown jail." 

He remembered one teacher who had his back to the students for so long at the chalkboard, that kids, including Fitzsimmons, had time to climb out the window and roam up and down Broadway.

“I benefitted a lot from my wandering childhood,” he said.

Fitzsimmons got his start in comedy in high school – after eighth grade here “it was strongly suggested to me that I move along" and he attended Rye Country Day school – when he performed in a talent show. Visiting the city as a teen he would go see improv and acts at venues such as Catch a Rising Star. In college in Boston, “about 50 yards from my dorm was a comedy club.” By senior year there, he was doing stand-up by night and attending classes by day.

Pursuing a comedy career was “not even decision,” Fitzsimmons said. More like a dare that seemed reckless at first and he went for it and got hooked. Despite “writing jokes and getting feedback and being completely free and creative, it’s not a great life.”

He travels a lot, spending perhaps too much time away from his loved ones. (Though he does make a point of coming this way for part of Christmas every year.) He said he couldn’t say it’s a happy life exactly – too "fleeting" a state – but satisfying. And Fitzsimmons said he has much to be grateful for.

As a boy, Fitzsimmons saw movies at the Music Hall when it was still a theater – Herbie The Love Bug, Blubber. “It’s always been my dream to do stand up there in front of friends and family, get interviewed by the local paper.”

So, turns out (if you call this a "paper"), I've helped part of Fitzsimmons’ dream come true, and you can too by attending his show Friday. 

Tickets are available at the Music Hall for Friday, September 14 at 7 and 9:30 p.m. shows here. 

Like us on Facebook  |  Follow us on Twitter  |  Sign up for our newsletter