Jay Leno Wins Hasty Pudding Man of the Year Award

The Tonight Show host visited Conan O’Brien’s alma mater Friday night, donning a bra and heels to accept the Hasty Pudding’s Man of the Year award. How mean were the Harvard kids to the comedian? Samuel P. Jacobs reports.

02.04.11 10:40 PM ET

Jay Leno showed up at Harvard Friday night, the old stumping grounds of a certain red-headed rival, to receive the Man of the Year award from the Hasty Pudding Theatricals, a long-running undergraduate tradition

Before receiving the ceremonial golden pudding pot—and legions of kisses on his Jay Leno-size chin—the comedian endured a 20-minute ribbing from the young actors about what exactly transpired between him and Conan O’Brien last year.

“He’s inspired millions,” the audience was told. “Millions of viewers to switch to TBS.”

When the laughs started to flag (“Like Genghis Khan, he’s conquered NBC… and his jokes are only relevant in the 11th century”), Leno let the crowd know that O’Brien would be last of his kind.

“I don’t think they have any more late-night hosts coming from Harvard,” he said.

Soon, as per tradition, Leno was in drag himself, gamely putting on green heels, a red wig, and a bra made of flashlights.

The roast was a promo for the Hasty Pudding—said to be the oldest dramatic society in the U.S.—and the premiere of the group’s 163rd musical, Kashmir If You Can. Once a refuge for Brahmins looking to blow off steam, today the group is known for its campy puns and campier costumes.

Leno’s selection as the man of the year for anything is a little funny—and not in the funny ha-ha way. You’d have to look past Mel Gibson (“Man of the Year,” 1997) to find another entertainer who played a more outlandish villain in Hollywood for his starring role in the Great Late Night Caper. Was it all meant in jest?

Of course, the Leno selection also seemed like a joke because O’Brien, the guy he seemed to screw out of the Tonight Show duties, is the patron saint of comedy at Harvard. Conan celebrated his 25th reunion last spring. Now, Leno is a Boston boy, a graduate of Emerson College and raised in nearby Andover, Massachusetts. But the renovated New College Theater stands around the corner from the Harvard Lampoon, the society where pale and funny young men (now plenty of women, too) goof off and then cartwheel to Los Angeles to write for The Office.

So was the whole night a diss for Conan?

Mo Rocca, the onetime Pudding president, says if it is, good for the dudes in heels.

“If the guys at the Hasty Pudding show are courting controversy by picking Jay, I'm all for it. Anything that brings attention to the place that allowed me to dress like a woman—outside my home—is fine by me,” the former Daily Show correspondent said.

Leno has “inspired millions,” the audience was told. “Millions of viewers to switch to TBS.”

Andy Borowitz, the New Yorker humorist and a member of Lampoon during his college days, says he doesn’t see what’s so funny. “Sort of feel the Leno-Conan story is over,” he wrote in an email.

Leno said he felt the same as he try to put a damper on any such talk at a post-roast press conference.

“It was totally separate. Conan is a fine performer,” Leno said.

One recent grad, a member of both Pudding and Lampoon, said O’Brien should be grateful.

“I don't think Conan's really sweating this one. In the grand scheme of things, missing out on a bunch of Harvard undergrads nervously forcing him to wear a bra and heels is one of the better things to happen to him this year,” Christopher Schleicher told The Daily Beast.

Everyone from Theodore Roosevelt to J.P. Morgan to Jack Lemmon hammed it up on the Hasty Pudding stage during their college days. The Man of the Year award started in 1967, 16 years after a woman first got the honor. Among the male recipients of the honor: Bob Hope, Paul Newman, and Lemmon. Justin Timberlake accepted the prize last year. Julianne Moore, who drops her Rs during primetime as Nancy Donovan on 30 Rock, was honored with a parade a week ago.

Leno, who came to Cambridge to do some his first shows, said he knew this history well.

“I was always the kid with his nose to the window, looking and following this organization,” Leno said from the stage.

He then choked up. He blamed a hairball from his wig.

Leno first appeared on The Tonight Show in 1977—the year that legendary host Johnny Carson picked up a pudding pot of his own. It was Jack Lemmon, not Carson, who Leno wanted to talk about once the roasting ended. When Leno was working the comedy clubs in Boston, he had a job at an auto dealership and wound up the chauffeur for a number of honorees—Peter Falk, Faye Dunaway, and, in 1973, Lemmon. Years later, when Leno moved to Los Angeles, the two comedians became neighbors.

Lemmon, Leno said, would tease him.

“Hey, did you get the Hasty Pudding award yet?” Lemmon would ask.

Now, Leno has his answer.

Samuel P. Jacobs is a staff reporter at The Daily Beast. He has also written for The Boston Globe, The New York Observer, and The New Republic Online.