(FORTUNE Magazine) – Bob Anzel is visibly worried. Here it is, 7 p.m. already, and the comedy club where he works, Stand-Up NY, is virtually empty on this crisp autumn evening. Maybe it's the presidential debates airing that night, he surmises. Or it could be the Yankees, who are mired in a heated playoff series with the Seattle Mariners. Still, one can't help but wonder why this evening's bill isn't drawing in hordes of young urban professionals from across the tristate area. After all, this is the grand finals of the club's third annual Funniest Stockbroker competition!

The field has been narrowed in previous tryouts from ten would-be standups to five--one of whom has bailed out at the last minute. All are competing for the grand prize: a paid night's booking at the club, which has played host to such big-name acts as Jerry Seinfeld, Billy Crystal, and Denis Leary.

The Funniest Stockbroker contest might seem to some like a competition for the title of "Hippest Amish" or "Most Promising Presidential Candidate." Nevertheless, Anzel, who runs the club's competitions, insists that stockbrokers as a rule are pretty darn funny--not quite as hilarious as teachers, but much funnier than therapists ("The worst," he pronounces). "Despite appearances tonight, this has been very, very successful," Anzel is quick to point out. "Normally this room would be about three-quarters full." Again he scans the empty tables, then comes up with yet another explanation for the poor showing: "It's because the bull market is over!"

A crowd of ten people--all friends of one contestant--does show up eventually. None of them are stockbrokers. But that does not deter the evening's MC from unleashing her newly penned barrage of broker jokes (such as her ruminations on why she was chosen to host the contest: "I own stock, I'm broke, and I'm a 'her'!" Hey, is this thing on?).

The first of four white male contestants, dressed in a white shirt and necktie beneath a trench coat, takes the stage. His act is filled with standard standup flourishes like "Can you believe it?" Unfortunately, that's often the whole joke--as in, "Now we have Hillary, can you believe it?"

By the time Jim, the second act, bursts on-stage, the audience is primed and ready. "Anyone have tech stocks today?" prompts the well-dressed comic. "When the market goes up, they think we're real funny," he says, without a hint as to who "they" might actually be. "When the market goes down, the joke's on them!" It's the sort of giggler, apparently, that makes you laugh on the inside. Jim dives right into Wall Street humor, concentrating for the most part on the intersection of high finance and dating. Take the woman with an uncanny ability to pick stocks he met. His continued pestering for more tips killed the relationship: "She said, 'James, I just can't do this. I feel like you're just pumping me for stock ideas. You don't care about my body!' " Somehow, Jim's charming vulnerability makes a lone audience member snicker. His biggest applause, however, comes when he stares into the spotlight and admits: "I forgot what comes next."

Painfully, the third contestant opens his act by confessing, "I'm an ex-stockbroker, actually. I lost my job. Questionable practices." Like Lenny Bruce in his later years, he does not appear to be joking. "You guys have seen the movie Boiler Room? That was it," he elucidates. "If a white-collar criminal embezzles $47 million, what does a blue-collar criminal do? Whore drill bits?" (Pause. Grin at the audience. Wait for heckler.)

Hold on a second. Aren't Wall Street wits supposed to be the source for all those disturbingly funny e-mail jokes and "top ten" lists--the tasteless chain mail that seems to circumnavigate the globe just hours after the latest sex scandal or airline crash hits the news? Aren't brokers--those big, bawdy, rumpled Scotch drinkers--supposed to be a backslapping hoot? How else can they compete with $7.95 online trades?

Good questions all. But they will not be answered by the final contestant of the evening: "I am not a stockbroker," confesses Jeff Stein, the man whom the table of ten has come to see. This may explain the fact that he is actually funny. He stays away from financial humor ("I had stockbroker jokes too, but most of the people here I know. They're in corporate communications"), sticking instead to tried-and-true topics, such as traveling in Europe and the trials of being a gay man. Most of the jokes are very off-color, and the crowd eats them up. One of the few that can be repeated describes his fruitless hunt for intimacy in Europe. "The closest I came to getting some was when I forgot my cigarette lighter and got patted down in Heathrow airport."

Jeff Stein is clearly the winner, followed by charmingly vulnerable Jim--though all contestants, either as a prize or punishment, get a videotaped copy of their performance. Stein--who is pursuing a standup career in earnest, playing amateur nights two or three times a week and working in equity research at Bear Stearns only to pay the bills until his career takes off--admits that he could be considered "brokerish" only among other comics. "Most comedians don't work, or they're waiters or service-industry professionals," says Stein. "So if you wear a suit, you're a stockbroker."