Justin R. Timberlake knew he would be receiving the Pudding Pot, but he didn’t know that Lady Gaga, Britney Spears, and Lance Bass would be on hand to help him bring his sexy back.

Facing an enthusiastic audience in a packed New College Theatre, Timberlake accepted his Man of the Year Award from the Hasty Pudding Theatricals Friday night, and in the process, wore a bra with gift boxes affixed at the breasts, danced in a reunion with his former ’N Sync bandmates, and fed Britney Spears pudding.

Entering a dimly lit theater as a band played jazz in the background, Timberlake, wearing a grey J. Lindeberg suit with a matching grey fedora, sat in the center of the fifth row and endured a relentless roast from Pudding producers Stephen L. Rola ’11 and Kelly M. Conley ’11 that touched on almost all aspects of his career.

Rola joked about Timberlake’s beginnings as a cast member on “The Mickey Mouse Show” alongside future fling Spears, which he said “marked the first but not the last time Britney would open for our Man of the Year.”

Rola then listed the titles of some of Timberlake’s songs—“FutureSex/LoveSounds,” “Sexy Ladies,” “SexyBack,” and “Love Sex Magic”—prompting Conley to quip that she was looking forward to a future song from him titled “Sex Sex Sexy Sex Love Sex.”

With a shake of Rola’s hand and a kiss on Conley’s cheek, Timberlake took to the stage, but the humor was not to cease, as Rola misidentified him as a singer in the Backstreet Boys and 98 Degrees. Soon enough, though, Rola realized who he was—“the guy who put his ‘d’ in the ‘b.’”

Timberlake’s digital short from “Saturday Night Live” continued to be a running joke in the performance. In an effort to bring Timberlake’s “sexy back,” a Pudding cast member said he would have to do a reprise of the sketch. He said the box would be perfectly sized in hopes of being environmentally friendly. Timberlake was then handed a giftwrapped package about the size of a ring box attached to a belt, which he placed around his waist.

Faux cameos were abound in the roast, with Lady Gaga—whose sexuality Rola said was described by ’N Sync’s song “Bye, Bye, Bye”—making an appearance and Spears—dressed in a puffy, pink plaid skirt and pigtails—singing “One, two, three, those are the bypasses I need.”

Throughout the roast, Timberlake’s countenance ranged from inquietude to imperturbability. In the end, he told the audience he never felt more like a man and that the award was “cooler than any Grammy or Emmy or,” at which point the audience cut him off with applause.

Later in a press conference, Timberlake said that the key to being successful was to “continue to be inspired,” calling 2010 “the decade of the entrepreneur” and asserting that the youth have a strong role in that.

“I think more and more young people are starting to go against the grain, and I think it’s because they’re not afraid to be inspired,” he said.

At the press conference, Cambridge City Councillor Marjorie C. Decker gave Timberlake the award of “Cantabrigian of the Year.”

Timberlake joins a list of celebrities dating back to 1967 who have received the honor of Man of the Year, including Bill Cosby, Clint Eastwood, and last year’s recipient James Franco.

Following the roast, the Pudding debuted their 162nd production, “Commie Dearest.”

—Staff writer Naveen N. Srivatsa can be reached at srivatsa@fas.harvard.edu.

This article has been revised to reflect the following corrections:

CORRECTIONS: February 10, 2010

An original version of the Feb. 8 news article "Hasty Pudding Roasts Timberlake" incorrectly described the clothing worn by the actor playing Britney Spears.

In addition, the article stated that the actor sang "One, two, three, lose the bypasses I need." In fact, the lyrics were "One, two three, those are the bypasses I need."