‘There’s Something About Ben’

In three decades of acting, Ben Stiller admits that he’s had some challenging roles. “‘There’s Something About Mary.’ There were some tough scenes in there,” he told a very young questioner at Harvard tonight (Feb. 23). “Don’t see it, though.”

But Stiller’s most challenging recent scene probably happened onstage at the Zero Arrow Theatre in Cambridge, when he had to slip on high heels, a silvery bra, and blond wig. Facing his wife, actress Christine Taylor, in the audience, he said: “Just like at home, honey.”

The bra and wig is a traditional challenge faced by every Man of the Year – each a famous actor on his way to the coveted golden Pudding Pot, awarded annually by Hasty Pudding Theatricals, the oldest collegiate theater troupe in the country.

Stiller – a veteran of 47 films and three decades of television as an actor, producer, director, and writer – matched his wits with Hasty Pudding roast masters Evan Eachus ’08 and Scott Wilmore ’08. To get to the award, the Manhattan-born entertainer had to dodge barbs about his twice-canceled “The Ben Stiller Show” of the early ’90s; catch a dose of biting reality about his repetitious roles (a fat-obsessed trainer in both “Heavyweights” and “Dodgeball”); and get strung up for “Cable Guy” – “the disaster movie of the summer,” said Eachus of the 1998 Stiller-directed flop.

Then there was the throwing contest, in which Stiller was given the chance to dust off a “few dark spots” on his resume by firing dodge balls at movie posters (“Envy,” “Along Came Polly”) – then at a “pretty little girl” in a frilly dress. That is: one of those Hasty Pudding college boys in drag.

But Stiller fought through the final challenge in custom high heels (he has big feet for a modest-size man), a wig, and a do-rag headband. His mission: a “walk-off” with his Frat Pack, many-film collaborator Owen Wilson, in a pretty wig himself. (It was another one of those Hasty Pudding boys in drag.)

By 8:32 p.m., Stiller got his Pudding Pot prize in hand, while submitting to another tradition: a two-cheek kiss from those ubiquitous boys in drag – male smackers that left big lipstick prints. “To think we had dinner together before this,” said Stiller. “We’re all different now.”

He had another comeback. “I’ll stand by ‘Along Came Polly’ – I like the makers of it,” said Stiller. And he had an admission about the accuracy of the jibes: “You hit the nail on the head many times.”

And Stiller, still in wig and bra, had a reflection on the gleaming Pudding Pot: “For somebody who never could have even gotten close to getting into Harvard,” he said, “this is even better.”

Minutes later, in the screening room at Zero Arrow Theatre, Stiller appeared with wiped cheeks, and – shorn of the glittering bra – dressed again in his neat blue jacket and tie.

Wilmore was there with him, facing the lights and action of a room full of press, and so was Hasty Pudding’s press manager Joshua Lachter ’09.

“This is obviously much more exciting than my nine months at UCLA,” he said of his one-day sojourn at Harvard, where a visit to the Lampoon Building – “a set from a Harry Potter movie” – was his favorite diversion of the day. “I was not into college when I went and I was unprepared when I went.”

But Stiller promised to make it up with his children (Ella Olivia, 4, and Quinlin Dempsey, 1). “We’ve got to get our daughter into a really good kindergarten,” he said. “A kindergarten feeder school for Harvard.”

The 41-year-old actor said he loved Harvard. “It’s so iconic,” he said, “and just see how on-the-ball everybody is.”

Stiller also acknowledged his comic genes – parents Jerry Stiller and Anne Meara, a longtime comedy duo. “Both my parents are funny,” said Stiller. “But they’re so funny together … They’re such a well-oiled machine.”

He joked about his childhood, “I was forced into it – into white slavery comedy at a young age.”

Maybe the best question of the night: Who would he invite to an imaginary dinner party?

“Martin Luther King,” said Stiller, acknowledging an interest in historical figures. “Mama Cass Elliot,” he went on. “And Hitler – let’s see what happens.”