The class clown’s journey to professional stand-up

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By Sarah Wolpoff
Thursday, December 12, 2019 3:33 AM

Remember that kid in high school—the type who would amuse their fellow classmates by whistling bird calls in the middle of a lesson, driving the teacher to insanity thinking there could be a feathered creature in the room?

Vincent Pietrafesa was that student, and that’s one of several humorous tales he can recall about his precious days at Port Chester High School.

As the typical class clown, Pietrafesa said when reconnecting with his classmates at reunions they generally take no surprise in discovering he’s become a successful stand-up comedian. After all, he was the guy who would bring a bus full of football players to guffaw by mimicking the coach during after-game speeches on the ride home from away matches.

“A lot of people say they were the funny kid. It’s almost a cliché of what a comic is, and I’m the same way. I definitely was,” Pietrafesa chuckled. “I was the kid who just loved making people laugh. I was a good student, but I also liked to disrupt class; disrupt them to make them laugh. And I’d try to make the teachers laugh, too.”

Humor has been instrumental in achieving his life philosophy: to enjoy life. He enjoyed life in Port Chester, and in college, and is very much loving life today.

By day, Pietrafesa does marketing work as Vice President of B2B Products in New York City. But for the last decade, his night life has involved frequently attending comedy clubs—particularly the City-based Tribeca Comedy Lounge and Dark Horse Comedy Club—as a comedian under the stage name Vincent James.

With a last name like Pietrafesa, he had to have a stage name.

To celebrate the holidays, Pietrafesa is headlining at the Yonkers Comedy Club in “The Mistletoe Show” on Friday, Dec. 20. The show starts at 8 p.m. and tickets are $20.

To make it a real fiesta, he recruited a few other comedians to join—all of whom originate from Port Chester or Rye Brook. The show is hosted by Port Chester native Michael Williams, stage name Mic Darnell, and will also feature Sasha Guillaume of Port Chester and the man who got Pietrafesa into comedy: Rye Brook native Josh Filipowski, whose father Frank served as mayor of the Village from 1998 to 2004.

“We used to work together pretty often—me, Vinny and Sasha—when we first started doing shows. So, this is a bit of a reunion,” said Filipowski, a Blind Brook High School Class of ’97 graduate who now lives in Boston doing stand-up and teaching English to international students. “I’m excited for it. It’ll be fun to see everyone. It’s a special event, a reunion to get these 10573 representing guys back together.”

Pietrafesa graduated from Port Chester High School in 1996 and went on to SUNY Oswego to study communications and mass media. He didn’t enter the realm of stand-up until a few years after graduating college, when his old buddy Filipowski took him to his first open mic.

“I took a workshop at New York Comedy Club and started performing showcases and open mics,” Filipowski explained. It all began after he saw an advertisement in the paper asking: “Think you’re funny?”

“When I started, I would think to myself, ‘Vinny was always one of the funniest guys I knew.’ We played Babe Ruth Baseball together, we knew each other just by pretty much being neighbors, and he always made people laugh. He always made me laugh. So I called him because if anyone could be doing comedy, it would be him.”

At this point, Filipowski has introduced countless people to the stand-up world by running his own comedy workshop at the Cambridge Center for Adult Education. He’s performed in eight different countries where “some of my jokes don’t work in any of them.” His material often touches on word play, relationships, difficulties in learning new languages and health and well-being.

Living in Manhattan, Pietrafesa’s career in entertainment took off since that first open mic, where he remembers getting a mere handful of chuckles. The first time is always rough. Aside from at least five nights of stand-up a week now, the 41-year-old does voiceovers for corporate videos and hosts large-scale events—introducing speakers such as Magic Johnson and John Legend.

On stage, Pietrafesa said his routine is largely influenced by his experiences growing up in Port Chester. He cherishes his childhood and credits it with making him the man he is today.

“I love Port Chester, I really do. I mention it a lot when I’m on podcasts, on stage or on the road. I grew up in a time where neighbors played outside together. My neighbors were my friends, we had a great time,” he said. “I was there when we started having this ethnic boom, when different restaurants were coming in. I never went to Taco Bell because we had access to real authentic restaurants. I loved the diversity, it prepared me for life and acceptance and getting along with all people.”

Pietrafesa grew up on Soundview Street. Ironically, he jokingly admitted, it featured no dazzling view of Long Island Sound.

Specifically, Corpus Christi Church played a large role in his life. From kindergarten through fifth grade he attended classes at Holy Rosary School, and it became about much more than religion. To him, it was a family where he learned virtuous values.

There, he said, is where he discovered the essence of a true community. It’s also where he discovered fulfillment through volunteering, with initiatives such as Midnight Runs to provide clothing and toiletries to the homeless in New York City.

The premise of giving back stuck for a lifetime.

Pietrafesa’s good childhood friend Joey Bologna died in 2011 at 31 years old—a tragedy that hit him hard. To honor him, the comedian set up the Joe Bologna Scholarship Fund, and the last two years has awarded two Port Chester High School students $500 for college. He supplies half of the money and the Bologna family matches the rest.

“I just wanted to keep his memory alive,” Pietrafesa said. “Joey was the town thespian, the best actor in our school. He was in the high school band and was on the football team. He did so many things and was just a well-rounded individual. With the scholarship, the student needs to be going to a college, and we look for a student like Joey. He was a rare talent who excelled at different things, so it’s someone who is taking on a variety of different extracurriculars. It’s not about the grades, but about being a multi-faceted person.”

Every year, Pietrafesa and the Bologna family do a memorial show to celebrate the scholarship winners at The Palace Theatre in Stamford, Conn. It attracts a mixed crowd of attendees who are there to support Pietrafesa and the Bologna family, as well as comedy fans who are eager for a fun night.

The Palace being one of the largest venues he’s booked, Pietrafesa said he always feels starry eyed and honored to see his name on the same marquee that has displayed some of the greats—such as Tracy Morgan and Ron White.

Just like growing up in Port Chester, Pietrafesa said his routine revolves around his personal experiences. He refrains from delving into politics as many other comedians do—that’s not his style. Instead, he speaks to his own life observations, which lately have included the new experience of raising his 2-year-old son, Hudson.

“I take a personal approach to comedy. Talking about my life and different progressions of my life. Sharing how I grew up and being a father through my eyes,” Pietrafesa said. “I would say it’s personal and energetic. I try to put on a show. I really just want to make people laugh. Make people say, ‘that was worth getting a babysitter for’ or ‘that was a good first date.’”

To keep track of Pietrafesa and his shows, like his Facebook fan page “Comedian Vincent James,” check out his website at or follow him on Instagram at @thevincentjames.

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