Ross Bennett, Addicted to Comedy

Comedian Ross Bennett has a modern twist on the classic take-my-wife joke. “I’ve been married twice,” he says. “My first wife died, my second wouldn’t.”

Like all fine humor, the line is based in truth, although Bennett won’t talk about the particular truth that makes the joke funny. After telling it for so long, he confesses that he’s never found it funny, since it was born out of personal hurt. But audiences laugh every time. “And that’s what counts,” he says. “I need laughter. It’s like a drug to me.”

Bennett has been doing stand-up for forty years. Starting out at talent shows in South Florida, he moved to Chicago and San Francisco before ending up in Los Angeles in 1979. Along the way, he credits the San Francisco International Comedy Competition–a month-long “crucible” of stand-up comedy–with helping him hone his material. It would be another twenty years of road gigs before settling in the Mecca of stand-up: New York City. As he puts it, “New York City is the Mecca for people who don’t go to Mecca.”

On stage, Bennett is endearing, affable, an Everyman of comedy. He is your average, small-town guy overwhelmed by the pressures of urban living like parking. It’s almost as if your uncle got lost during intermission at The Book of Mormon and wandered onto the stage. His shtick is that of the hapless guy who expects the worst and is grateful for anything short of that. You can hear it in his line about casual sex in his twenties: “Whenever it happened, I was always thankful, appreciative, and mildly suspicious.”

Off stage, Bennett is anything but hapless. He is smart, focused like a ninja, and adept at pointing out the absurdities of life. He is also resolute. How else to explain his intentional departure from West Point before graduation to pursue his dream of stand-up? He had been part of the Cadet Acting Troupe at the Academy (The Music Man, Once Upon A Mattress) but wanted more. It was 1976, Saturday Night Live was new, and Steve Martin had soared to fame reviving the “comedian as idiot” persona popularized earlier by Peter Sellers. Bennett thought, “It’s now or never!”

And how else to explain the twenty-eight years of rejection before finally landing a spot on The Late Show with David Letterman? As he tells ithe was so nervous before going on that he couldn’t feel his legs, which felt like “cinder blocks.” Fortunately, the set was a hit, impressing both audience and host.

Bennett is a chronicler of contemporary comedy. He can recount, with interpretive insight, the evolution of stand-up from the early seventies to today. One such insight concerns Steven Wright, who was discovered accidentally by a producer who recognized his genius and thought what he needed was an audience that could appreciate his humor. So Wright went from performing in bars in Boston to The Tonight Show Starring Johnny Carson.

Such insights support Bennett’s conviction that long-term success in stand-up depends upon the strength of the material. “Anybody can kill,” he explains. “But how many do it with quality material? You want to be successful in this business? Write great lines and tell quality jokes.” Easier said than done, and Bennett points out that there is no magic formula for making people laugh. In another take on a classic joke–How do you get to Carnegie Hall?–he stresses hard work and stage time. For instance, he tells the story about red “X” marks on the wall calendar in Jerry Seinfeld’s apartment. When asked about them, Seinfeld explained that those were the days when he spent eight hours or more writing jokes.

Another Seinfeld story illustrates the importance of focusing on your own material and not anyone else’s. Bennett was working “middling” (i.e., the comedian between the opener and headliner) in San Francisco in 1981. Seinfeld was the headliner, and Bennett, an admirer of Seinfeld, nevertheless was determined to “bury” him.

“I went up and killed it. I left the stage to thunderous applause and my attitude was, ‘follow that, Jerry!’ But then Seinfeld gets up and within two minutes the audience forgot all about me. He was a genius with an impeccable work ethic, but I did not understand that at the time.” Underneath Bennett’s self-effacing demeanor is true humility. It’s a natural part of his personality, but it has been honed by ruthless self-examination concerning who he is and what he has to do to succeed. It also serves him as a teacher of new comics and writers at the Manhattan Comedy School. Like all great teachers, he has the ability to put his ego aside, be present to students, and listen.

“Ross taught me how to tell a joke,” says Anthony LeDonne. “Each time I told a joke-in-progress, he’d pause, then suggest a different setup or structure. He helped me become a stronger writer and a better comic.” Typically, Bennett spends more than three hours with a dozen students each week as they work, rework, and practice their material in front of each other. Slight changes in phrasing, a gesture, a pause can make the difference between one of LeDonne’s jokes “in-progress” and audience applause.

Judging from appearances, Bennett is a successful comic with a full schedule and excellent reputation. But by his own admission, he has difficulty accepting that he has not gotten further than he has. “It’s humbling to work at a job where you can’t help but judge yourself next to some of the greatest comics of all time. Still, I am driven to go further.”

In true Army style, you can almost hear General Patton declaring that he can move two divisions in forty-eight hours. Despite the other generals in the room snickering, Patton moved his divisions. One suspects that Bennett will do the same. How could he not? “I am addicted to comedy,” he says.

Want more? Go to Robert Brancatelli. The Brancatelli Blog is a member of The Free Media Alliance, which promotes “alternatives to software, culture, and hardware monopolies.” Note to self: You want to know what people are really like, open their microwave. I’m here all week.


  1. Ross is a great teacher and one of the funniest and nicest people I know. He helps you bring out the best in yourself and doesn’t let you settle for easy or cheap laughs. He may not have the recognition he deserves from the general public yet, but he has it from his fellow comedians.

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