The Hasty Pudding Theatricals awarded the Pudding Pot to their 2011 Man of the Year Jay Leno on Friday. But to get his golden reward, Leno first had to complete three tasks—make fellow talk-show host David Letterman laugh, prove his generosity to University President Drew G. Faust, and best the talents of Joan Rivers, Ellen DeGeneres, and Oprah Winfrey—all played by members of the Hasty Pudding cast.

The awards ceremony began with Nikolus A. Ray ’11 and Matthew E. Whitaker ’12—co-producers of the Hasty Pudding Theatrical’s current show “Kashmir if you Can,”—roasting Leno on topics ranging from his generally older viewer base to his conflict with Conan C. O’Brien ’85.

“In order to give our man of the year time to rest we considered moving our 8 p.m. show back two hours later,” Whitiker said.

But, Ray said, “We do realize that no one wants to watch a show that starts at 10 p.m.”

After the roast Leno was given a choice between signing a contract—another jab at his conflict with O’Brien—or completing three tasks.

“I’ll take the three secret tasks,” Leno said.

Leno first had to entertain talk-show host David Letterman, played by Ryan P. Halprin ’12, by proving that his prowess for reciting monologues surpassed that of Hamlet’s.

Leno recited lines from Shakespeare’s famous play, while Hamlet countered with monologues from Leno’s show.

“I think you’re funnier than Hamlet.” Halprin—as Letterman—said to Leno. “Reasons why—your face. I just love laughing at your face.”

Toward the end of the performance, Leno had to confront his late night rival, O’Brien, who came out on stage dressed in a janitor’s outfit with mop in hand.

For his third and final task, Leno had to confront three fellow talk-show hosts and “beat them at their own game.”

Joan Rivers, played by Matthew J. DaSilva ’12, forced Leno to put on a bra in the shape of a car’s headlights.

Ellen DeGeneres, played by Kyle J. Dancewicz ’11, challenged Leno to a dance-off to “Party in the USA.” Leno strapped on a pair of bright blue pumps, donned a red curly wig, and gyrated to Miley Cyrus’ famous tune.

Leno then competed against Oprah Winfrey in a celebrity name shout-out showdown. Charleton A. Lamb ’11, who played Winfrey, replicated Winfrey’s flamboyant shout-out style, but Leno emerged victorious. Lamb is an inactive Crimson editor.

Leno was finally able to accept his Pudding Pot after 20 minutes of good-natured humiliation, though the riotous crowd refused to let him remove his comedic costume during his semi-serious acceptance speech.