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Cruise Entertainers via Passport Magazine

Twenty years ago, Matt Yee ( would never have guessed he’d be generating the bulk of his income regaling holiday travelers with show tunes and double entendre dirty jokes (often while sporting a muumuu and a ratty blond wig). The Hawaiian-born son of financial advisors, Yee, who sang and played piano avocationally from the age of three, won a music scholarship to Dartmouth University and moved on to law school at the University of Pennsylvania.

“I was doing mergers and acquisitions in the boomtime 1980s,” he recalls. “You’re supposed to feel so fortunate having an opportunity like that, but I realized that I hated it.”

Yee walked away from his white-shoe firm feeling somewhat adrift. While finding his sea legs as a gay man during the height of the AIDS crisis, he dabbled in real estate development in San Francisco and, ultimately, back home in Hawaii. It was during this period that he returned to music, beginning to develop an act and stage persona while playing in gay piano bars.


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