RICHARD OSTERWEIL HAS CHATTED UP Elizabeth Taylor at a $1,000-a-plate charity ball, snacked on shrimp canapés at Harry Reasoner's memorial service and sat with Walter Cronkite at Phyllis George's wedding. He has talked shoes with Imelda Marcos and discussed the ballet with Jackie O. In a well-traveled tuxedo, sipping champagne, he has presence, decorum and a certain je ne sais quoi. What he doesn't have is an invitation.
If party crashing were an art form, Osterweil, 39, would be its Picasso. He is in fact a New York City painter (and a part-time restaurant coat checker) who during the past 15 years has invited himself to some 300 celebrity functions. He does it, he says, to be near fame—and food. "Crashing is the only thing I've ever been good at," Osterweil explains. Osterweil's urban adventures have been chronicled in Andrew Behar's Painting the Town, a quirky 80-minute documentary opening in several major cities across the U.S. In the film, Osterweil recalls schmoozing with Princess Grace and visiting Leonard Bernstein's relatives as they sat shiva (the Jewish mourning custom). He also reveals tricks of his trade, such as, "Always try to seem rich."
Osterweil, who is single, grew up middle class in Levittown, N.Y., the elder of two sons of a jewelry-salesman father and a social-worker mother. He crashed his first party in 1977, a bash for the Al Pacino movie Bobby Deerfield. Since then, he says, he has been tossed out of only about one in every four events. "It's difficult to humiliate me," he adds.
Osterweil does realize that his movie appearance may put an end to his crashing days. But his job checking coats at a dining spot near Lincoln Center will allow him some contact with celebs. Osterweil doesn't just hang up the garments of the rich and famous—he tries them on. "I've worn Bruce Springsteen's leather jacket and Lauren Bacall's rain-coat," he says. "How many people can say that?"
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