So here's Vince Sicari, just north of Times Square, telling jokes at four in the afternoon. It's one of those hospital-gray days when New York City spits in your face. At the famous comedy club Carolines on Broadway, down a flight of stairs, behind thick black curtains, Vince is hosting the happy-hour set. The room smells of flat Bud Light and mozzarella sticks. The cover charge is five bucks.

When holding a microphone, he's Vince August. It's his middle name, a pseudonym that seemed necessary back when he had something to hide. Vince calls his act "true and honest," a loudmouth version of the Regular Guy. He starts with a monologue about the weather, followed by a short bit about the Super Bowl. His eye catches an audience member with a shiny bald head, much like his own. Vince targets him.

"What would I do if I weren't me?"

The guy is a pilot. Vince spins some improv about the "Miracle on the Hudson" and Captain Sully, arguing that Sully is no hero. "He flew a plane and lost to a goose."

Various comics take the stage one by one. Vince does his own material between each set, growing raunchier and more aggressive as the afternoon drags into night. When describing his penchant for cunnilingus, Vince tells the room, "I can lick a credit card out of a wallet." He will be paid $100 for telling such jokes.


Vince, 44, is pale and stocky, a few inches under six-feet tall. In the lobby, a middle-aged woman stops him and says, "You're very funny." Vince leaves Carolines, feeds his parking meter and then shuffles across Broadway to the upstairs bar at Crowne Plaza, landing a table next to a window overlooking a glowing, pulsating Sbarro.

When he speaks, he moves his hands like a lawyer. There's a large appointment book under his arm. It's beautiful—black leather with gold-lined pages and "VAS" engraved in the lower right-hand corner. He keeps it with him at all times in case he gets offered a gig. The appointment book is more apropos for someone of a certain stature, like a judge, not a comedian.

Until recently, Vince was both. His double life could have been a 1980s sitcom, something farcical starring Tony Danza—if Tony Danza were bald. By day, Vince was a New Jersey municipal judge; by night, he was an amateur comedian and aspiring actor. And for a long time, those two worlds—and totally different career choices—coexisted just fine. That is, until the New Jersey Supreme Court, with much fanfare, forced him to choose. Pick one, they decreed: It's either the gavel or the mic.


Vince's parents never understood his comedic dreams because they weren't tangible in a way that jibed with their striving immigrant archetype. His father grew up in Sicily during World War II and often spoke about the bombings there, about being occupied, about seeing Nazi soldiers trudge past him. As such, he wanted Vince to be an accountant.

Vince reluctantly followed his father's wishes at Fordham, a short drive from his childhood home in New Jersey. "I was in the honors society, and I realized about my third year in, if I'm gonna be an accountant, I'm probably gonna climb the tallest building in New York City and jump off of it."


Later, when I ask Vince if that was a joke, he breaks eye contact.


At age 22, at the request of a concerned girlfriend, Vince began meeting weekly with a Jesuit priest at Fordham for counseling. He had been battling depression for nearly a decade, and in high school, he developed a penchant for fighting. Vince and his friends brawled at the Tavern in the Bronx, at Café Iguana on Park Avenue, at random bars on Long Island. If a fight was bad enough to make headlines, his friends would clip the article and save it in a scrapbook. He eventually tired of brawling, but his anger grew worse.


"Slowly but surely, I started to see what was going on," he says. "I never put my foot down and took control of my life. Was it to satisfy and appease my parents? Everyone kept telling me, 'You're good at this. You're smart. Just be an accountant. You're gonna have a great life.'"

During his senior year of college, Vince took a required class about business law. He failed an early exam—the first failed exam of his life. He begged the professor for extra credit and was told to participate in Moot Court, a mock-trial competition. "I got to play this character in front of the classroom," he said. "I wasn't thinking in terms of law, I was thinking, I have to win this argument. I have to win these people over. And it turned into my first performance. I went home and told my parents I wanted to go to law school. They were ecstatic."

Barely a year after passing the bar, Vince awoke one night and began speaking into a tape recorder over dead air in his bedroom. "Call it a vision. I ranted for an hour." He crafted jokes about growing up Italian, about going bald, "the dirty little secrets" of life. He tweaked the material for nearly six months, then gave the tape to a friend, John Mannion, asking for honest feedback. Mannion worked nights at ShopRite, stocking shelves when the store was closed. He played the tape for his graveyard shift colleagues; they laughed their asses off. Now Vince had the bug.


At 28, just out of law school, Vince was handling workers' comp cases by day and scouting places to perform at night. "I had never stepped into a comedy club in my life," he says. "And I didn't want to. I made a promise to myself that if I ever went to a comedy club, it would be as a performer, not as an audience member." He found an introductory course through Carolines and walked into the first class with an hour-long routine. "The guy who ran the course wasn't of use to me. In fact, he tried to change my material. He thought I was too edgy."

Only a handful of close friends knew that Vince had started performing. He kept it hidden from his brother and sister—and most definitely, his parents. "I didn't want this taken from me," he says. "It was like a kid that I wanted to nurture and develop into this unbelievable person. And the weird thing is, it's who I really am. When you say, 'who are you, really?' I'm more that guy than I am the guy who goes to court."

Day-to-day, Vince was still practicing law. He left his first job after a falling out with one of the partners—"I actually threatened to throw him out of a window"—and joined a criminal defense firm. He found an agent to scout commercial auditions, occasionally landing regional spots (Starburst, Geico, Priceline). On a given day, Vince would wake up, go to work, get wind of an audition, drive to Manhattan, try out for the part, drive back to Jersey, work on a brief, return to the city, perform a comedy set, then drive back to his office late at night. He'd change out of his suit and into jeans inside the bathroom of a Mobil station. He barely slept. "Anytime I was offered a spot, I took it."


The Daily Show with Jon Stewart is produced inside an unglamourous studio on 11th Avenue in Hell's Kitchen, closer to New Jersey than the pulse of Midtown Manhattan. Last year, Vince was asked to be the backup warm-up comic for the show's live tapings. Before arriving at the studio this afternoon, Vince was at work finishing a response to a summary judgment motion. "One of those must-win cases for me." Next to his black appointment book, he's clutching a copy of (201), a local Bergen County magazine. There's a small blurb about Vince under the headline "Favorite Local Celebrity," just below a photo of James Gandolfini, "Favorite Local Celebrity [In Memoriam]."

Backstage, about a dozen VIPs linger in a nondescript break room with cheap leather sofas. Their wristbands read "NOT A THREAT TO THE DAILY SHOW." A fading blue wall highlights January birthdays, the bubbly Kristen Schaal among them. Lewis Black walks by in a disheveled suit and pancake makeup. "How you doin' fucker?" he asks a member of the crew.


Vince stands in a hallway just off the kitchen. "I don't want to have any preconceived notions of who they are," he explains, pointing to the group. A warm-up gig is rooted in crowd work; Vince doesn't want to taint his improvisational instincts. In five minutes, the stagehands will shepherd the VIPs into the studio for pre-seating. The rest of the audience will enter from another side of the building. Vince will hang back, alone, and pace.

He has no dressing room. He won't get makeup.

Then, he'll walk out and have 10 minutes to set the stage for Jon Stewart.

In 2007, Vince received a call from a New Jersey township, offering him the role of part-time South Hackensack municipal judge. It sounded like a great gig.Vince took the oath of office and started sitting trial in January 2008, earning a part-time annual salary of $13,000. By the time he became a judge, Vince had branched out from the club scene to perform at private events. His bookings included Ernst & Young's "Entrepreneur of the Year" award show, a stranger's dining room, the hallway of a corporate Christmas party and a charity function in Eastchester, New York.


Five months into his first term, Vince underwent "Baby Judge School," a common course on best practices for new appointees. Among other things made clear in the "Code of Judicial Conduct," judges aren't permitted to reveal their political leanings or donate to charitable causes. Vince contacted the Administrative Office of the Courts and explained that, in telling jokes like the wallet bit, he was merely donating his talents—not money—to charity. Moreover, he was doing so as Vince August, not Vince Sicari.

Two years passed; Vince never received a formal response.

He continued to sit trial, in addition to working new cases as a lawyer and cruising for comedy gigs. "I could be at the club and get a bail call," he says. "I'd have to find a private room somewhere or go out to the street, jot down notes, set bail, go back into the club and tell jokes."


In 2010, Vince received a formal response from the Administrative Office of the Courts. It instructed him, point blank, to resign. He quickly filed an appeal. By now, Vince was a regular on the ABC hidden-camera show What Would You Do? The show's premise: Manufacture an uncomfortable situation in a public space, then observe how people react. Vince was cast in various controversial roles, including a gay basher and a waiter who refused to serve a black father dining with his white daughter.

Canon 2 of the "Code of Judicial Conduct" requires judgesto not only avoid impropriety, but the mere appearance of impropriety. Specifically, to act at all times "in a manner that promotes public confidence in the integrity and impartiality of the judiciary." The advisory committee saw Vince's characters on What Would You Do? and filed a second complaint. Vince countered with a second appeal. Now it was up to the New Jersey Supreme Court.


On February 26, 2013, Vince and his pro-bono lawyer squared off with Deputy Attorney General Kim Ringler in front of the seven state justices. The case had gone quasi-viral; Vince was receiving tweets and calls of support from all over the world. Papers in London, Canada and Brazil covered the hearing, along with many U.S. outlets. A casting agent would soon fly Vince out to L.A. for a week of pitch meetings. Inside the hearing room, various men and women in suits were arguing over the definition of comedy. "I felt like a kid at dinner when the parents are having a discussion like he's not there."

Vince agreed to turn over 30 tapes of What Would You Do? along with three different stand-up sets for judicial review. But he refused to relinquish Vinsanity, a 90-minute performance-film that he made in 2004. No traces of the film exist on the internet, and Vince maintains that he would have to "tear his house apart" to find the master. In the film, according to a lone, anonymous summary on IMDB, Vince seeks the help of a psychiatrist "to help him move away from his angry rants about his personal life, racial stereotypes, religion and society in general."

Vince's lawyer begged him to hand Vinsanity over to the court, but Vince refused. In his eyes, the request violated a self-imposed statute of limitations. The film was made in 2004; Vince became a judge in 2008. "Are you the same person in 2004 that you are now?" he asks, his face filling with rage. "What about what you did in college? I wasn't a judge in 2004, and no one anticipated I would become a judge."


The prosecution insinuated that Vince was hiding something. "That blew my fucking mind."

Seven months later, the Supreme Court announced its decision. In the end, it was about perception. The ruling argued that since municipal court is the only court in which most people will ever appear, it's imperative that a judge conduct his or her personal life in a manner that preserves integrity. "Vince Sicari, the lawyer, may be free to pursue a parallel career as an actor and comedian. Once he chose also to serve as a municipal court judge, however, he became subject to the Code of Judicial Conduct."


The decision acknowledged that Vince had never conducted courtroom proceedings "in any other manner than a professional one." It confirmed that the characters Vince played on What Would You Do? were scripted, though it acknowledged that the general public might not be aware of that fact. Furthermore, it alluded to the possibility that a person who attends a comedy club in New York might potentially find themselves sitting before Vince in a New Jersey courtroom. The decision noted specific instances in which Vince's comedy demeaned certain groups and revealed his political leanings. Among the jokes excerpted: "Barack won. And it's weird, because, like, I voted for him. But, I almost don't know ... do I congratulate black people?"

A close read proves that the court was not forcing Vince to step down from the stand, something the advisory committee initially tried to do. It simply informed Vince that he couldn't remain a judge and a comedian.

After the decision was published, Vince called his boss and mentor, the Honorable Roy F. McGeady, Presiding Judge for the Municipal Courts. Later that morning, Vince drove to McGeady's office, hugged him, thanked him and through tears, resigned.


He refused to relinquish his judge's robe, however. "I have this crazy notion that maybe it'll be in a Planet Hollywood someday," he says. "Autographed."

So here's Vince telling jokes on The Daily Show stage, beneath rows of hot rainbow lights. He walks the length of the studio floor, bobbing between, but not in front of, expensive TV cameras. He logs every performance. Tonight is number 1,790. He only keeps count if there is an audience present.


Vince took time off when his father passed away just after the New Year. "I've performed almost 2,000 times; he came twice." In the final years of his life, Vince's father beamed with pride knowing his son had become an American judge. And while Vince's decision to leave the bench pained his father, the two made peace just weeks before his death. When cleaning out his father's belongings, Vince discovered a folder of Vince August-related news clippings. His eyes turn red and glass overwhen he describes it. "Maybe he just never wanted to swing me one way or the other."

On stage, Vince is far more relaxed than he was a few days earlier at Carolines. He calls out a young commercial real-estate salesman, then targets a probable stoner. (It turns out the guy is visiting from Colorado.) He spots an elderly woman in the front row and calls her "Betsy Ross" before inviting her to drop an F bomb into the microphone. After about 10 minutes, Vince introduces Stewart, hands him the mic and walks off the set. The room is buzzing.

Louis C.K. is the guest. He's there to promote his 1998 black-and-white film Tomorrow Night, which he'll release the next day. C.K. reminisces about how Stewart loaned him $5,000 to help make the film back in the 1990s. Stewart talks about how they used to sit around Manhattan diners late at night, coming up with scores of ideas but never executing any of them. The conversation is sweet and nostalgic.


Vince didn't watch the segment from the wings. Nor did he listen from the break room backstage. No, by the time C.K. and Stewart were laughing at their collective struggle, Vince was driving up the West Side highway, back across the George Washington Bridge, New York City fading in his rearview mirror.

In due time, he'll be back at Carolines, where C.K. is among scores of comedians framed on the wall. He'll tell jokes as plates of fried calamari sizzle by. He'll liken his pale complexion and bald head to that of a sex offender. He'll ask people what they do, and no matter the answer, he'll find some way to mock them. He'll get laughs, real or fake. He'll never mention that he was once a judge. That part of his story doesn't make it into his routine. As far as Vince is concerned, those two things are still separate. That was his career; this is his dream.

John Hendrickson is contributor to Playboy Digital who last wrote about Nick Gilronan, the man with the smallest penis in Brooklyn. Follow him on Twitter @JohnGHendy.


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Photos by David Yellen