Phil Valentine never wants to leave his calendar blank.
The Riverdale comedian is committed to writing jokes daily, using his calendar to serve as motivation. The more he writes jokes about being single and things he observes in his daily life, the more he’ll improve his craft.
Valentine has always had a genuine curiosity about what makes a successful comedian. He’s always admired performers like Dave Chappelle and Bill Burr, yet found comedy to “be so cool and so out of reach” because he never knew how people got involved in the industry and how they were able to find open mic nights to perform at.
“It’s not like starting a band,” Valentine said. “It’s tricky to get into.”
So instead of just waiting around to figure it out someday, Valentine took action. Three years ago, he took a one-month comedy class in Manhattan, learning everything about how to find gigs and how to properly write jokes.
Taking that big leap was exactly what Valentine needed to start taking a potential comedy career seriously.
“I didn’t want to look back and say, ‘Why didn’t I do it?’” he said.
The class also taught Valentine a thing or two about how comedy is different when you’re joking with friends, as opposed to performing for an audience full of strangers.
“If you’re funny with your friends, the setup isn’t just the one line you say before,” he said. “The setup is the conversation, and the mood, and who’s hanging out … so a lot goes into that. If you’re presenting it on stage, you have to trim all of that fat and try to evoke the same emotion.”
So when he writes, Valentine can easily cut to the humorous part of an observation or interaction with someone that works best with an unfamiliar audience.
“Little things … will leave a little tick in my head where I’m like, ‘There’s something about that,’” he said. “Then you go back and you write it, and you try to just exploit the little moment.”
These days, Valentine is bringing his comedy to stages across New York City. Since taking that class, he also started Cross the Bridge Comedy, a night of laughs featuring New York comics.
“I wanted to create an avenue to give really funny comedians who I know a chance to come up to my borough and to a great venue,” Valentine said.
Cross the Bridge all started at An Beal Bocht Café. Valentine had come to love the West 238th Street eatery over the 10 years since Manhattan College first brought him to Riverdale. And it wasn’t until he started pursuing comedy Valentine realized An Beal would be a great place for standup comedians to entertain patrons.
“What I love about An Beal for a show is there’s no TVs,” he said. “So you’ll never have to compete with a Mets game.”
The comedy show started two years ago, but Valentine already has taken it to other venues on the Lower East Side, Brooklyn and Beacon up in Dutchess County. On July 26, Cross the Bridge celebrates its 10th show at An Beal Bocht.
Valentine considers shows here to be special because he wants to continue encouraging comedians to perform in the Bronx. It also makes Cross the Bridge a “flagship show” for Riverdale.
And it doesn’t hurt that a Bronx audience is more active than others, at least according to Valentine.
“The Bronx crowd loves to be in the show,” he said. “They love to laugh. They can take a joke. It’s always great.”
Cross the Bridge Comedy’s An Beal show is free, which is something Valentine does on purpose, even though he jokes he might regret it one day.
“That’s kind of an important thing to me, to deliver comedy for free,” Valentine said. “There’s just so many great comics and so many great people who love comedy, and I want them to come in and have a drink and laugh their heads off for a night. I don’t want their money.”
Three years into his comedy journey, Valentine feels he’s better with words and can express himself more than he could before. It’s even forced him to be a little more positive in his day-to-day life.
“I think I’ve learned to find the silver lining in a lot of things because I frequently will go to the joke quickly in my thoughts,” Valentine said. “So for better or for worse, I take things a little more lightly because I try to find humor in things.”