For over 27 years as master of Timothy Dwight College, Robert Thompson has seen Yale transition from an all-male institution to one welcoming the opposite sex and has witnessed an accompanying diversification of the student body. But Thompson, currently the longest serving of the 12 residential college masters, is also quick to add that some things do in fact stay the same.

“If one thing’s stayed constant, its ‘weenie,'” Thompson said, sitting in the TD Master’s House. “What do you think of when I say, ‘weenie’? It’s someone who doesn’t have time to go out because they’re working all the time. When you call someone a weenie, you challenge them to live a life less buried. There were weenies in the ’50s, ’60s ’70s, ’80s, ’90s and there are weenies now.”

In honor of Thompson’s long tenure as master, TD threw him a surprise party last Saturday night in the college dining hall. At the party, attended by students and faculty, Thompson was able to demonstrate the one maxim that he shares with his students: “work hard, play hard.”

“Of course I had to dance,” he said with a wink.

Thompson’s master’s house, filled with African and South American paintings, textiles, sculptures and pottery, is reflective of his academic and musical tastes as a history of art professor. A connoisseur of African art in particular — he dons an African mask every Halloween — “Master T” is credited with bringing culture to his tight-knit college. His party on Saturday featured hip hop, salsa, and “pure Cuban rumba” in his honor.

“He speaks more languages than anyone I know, loves rap, hip hop, African culture, and has taken a huge affinity to dressing coolly,” master’s aide Sadiq Abdulla ’05 said. “He’s very bourgeois, a very chill person, one of the cooler adults I’ve ever met.”

Renowned for his Thursday night study breaks which feature samba bands and guest break-dancers, Thompson has a unique philosophy about mastership.

“I don’t think it means, I am your master,” he said. “I think it’s a chance to show that you are the master of certain disciplines. Just like someone immersed in Japanese politics, or French literature, you strive for total immersion in a discipline so that following that passion is less a discipline — it becomes bliss.”

Asked about the highlights of being master, Thompson said he derives great pleasure from working with the Chubb Fellowship, a program based in TD that brings distinguished men and women in government and public service to campus each year. Mexican President Ernesto Zedillo came to TD on Thursday, and Thompson said Sens. Hillary Clinton and John McCain — and “if we get really lucky,” current Broadway star Kathleen Turner — are expected to come next year. Thompson recounted when Argentine President Raul Alfonsin visited campus in 1983.

“For the three days he was here, Argentina was run [from] Yale,” Thompson said.

Guests for the Chubb Fellowship vary from the politically active to the physically attractive. When actor Robert Redford visited the TD dining hall, Thompson said he had never seen so many girls wearing lipstick and skirts.

“Women looked like wo-men,” he said, emphasizing the two syllables. “Women with an exclamation point.”

Though he maintains he does not regret any decision as master, when asked about the 2002 cancellation of the Erotic Exotic, a “the-less-you-wear, the-less-you-pay” dance that was a TD tradition for many years, Thompson displayed clear distaste for the subject.

“Oh God, are we going into that?” Thompson said. “That was four years ago, I’m done with that.”

But whatever controversy still surrounds that subject, it is clear that the admiration between student and master is reciprocal.

“Because of his experience, he frames issues effectively to get things done that otherwise might not get pushed through Yale’s bureaucratic system,” TD resident Neil Chatani ’08 said. “His long tenure as master is a tremendous asset to us. He is highly regarded among the Council of Masters, and makes our voice count.”

For his part, Thompson is genuinely surprised when asked if he will ever tire of being master. He said his experiences with meeting dignitaries and movie stars, as well as his every day interactions with students — he does a “Paul Revere” walk around TD at night — provide more excitement than he can convey.

“Eventually, I will write a book called ‘College!'” he said. “I’ll call it ‘Walden College’ in the state of Washington to disguise our secrets, of course.”