(Continued...)

In the prologue to his best-selling book, How to Lose Friends & Alienate People, writer Toby Young recounts his experience crashing the infamous Vanity Fair Oscar party in 1994. The unabashed scribe chatted up and successfully pissed off Amanda de Cadenet and Kenneth Branagh before being bounced while talking to Nancy Kerrigan. Young, who had pretended to be a fellow journalist whose name was on the list, was foiled when his "namesake" showed up at the event.

Yet the door policy for the famed magazine affair can be just as brutal for invited guests as for interlopers. In 1996, this time on the payroll at VF, Young managed to snag an invitation to the lowly latter part of the event. He was given orders not to show up until after 11:30 p.m. but defiantly arrived at 10 and finagled his way in with sweet talk. "There are so many checkpoints and its organizers are so officious, it's like trying to get into the headquarters of the Waffen-SS in Nazi Germany," he says. Yet somehow, he recounts, a reporter for The Star breezed in sporting a piglet on a leash, claiming that it was the lead in Babe, which was nominated for Best Picture that year.

Throughout his 30-year crashing career, Osterweil has opted to stay within his New York stomping grounds. For his inaugural episode, in 1977, he snuck into the premiere of Al Pacino's Bobby Deerfield at Tavern on the Green by entangling himself in Jacqueline Onassis's entourage. As a result, Osterweil is still often asked by tabloids to speak as a pundit regarding the political royals and quoted in print as "Kennedy pal." Unfortunately for him, after his documentary, Painting the Town, was released in 1992, he was prevented from attending Onassis's funeral two years later. Having successfully navigated three security checkpoints, Osterweil was about to enter using the name of a Kennedy advisor, but "the guy in charge of protocol had seen my movie."

Though crashers don't always make it all the way into the event, or stay long enough to enjoy the entire party, some get a buzz from just passing a checkpoint or two. San Diego-based crasher Scoobie Davis recalls one such experience. Despite the fact that he didn't make it inside the Oscars, he got as far as the red carpet arrivals. "When I did get to the red carpet it was more of a fluke," he recalls. He had had some prior party-crashing experience at the time—mostly post-movie premiere events. On that day, he happened to be helping shoot a commercial for a limousine service on Sunset Boulevard when the flush of fancy to crash struck him. He befriended an Oscar-bound limo driver, convinced him to lend out his pass, and proceeded to make a copy of it at a Kinko's down the street. "We were totally clowning around," he says. "There was all this talk on TV about enhanced Oscar security. This was the first after 9/11." Yet they made it through checkpoint one—the paparazzi ghetto—and even got coverage from the Associated Press and CBS News. "There were throngs of people cheering and flashbulbs going off," he recalls.

Osterweil experienced his own pinnacle flashbulb moment when he came out of retirement to sneak into Liza Minnelli and David Gest's wedding in 2002 (an event he chronicled for The New York Times). For this special occasion, he opted to double up, bringing a gal pal as a date. Previously, the two had much success by posing as a bickering husband and wife. "No one likes to interrupt an arguing couple," he points out. This time the plan was a little different. Amid a paparazzo's wet dream of legendary celebrities including Lauren Bacall, Mickey Rooney, and Michael Jackson, they hurriedly pushed their way up to the entrance. Osterweil then stammered, with a dire look on his face, "Excuse me, is there a ladies' room around? My wife is not feeling well." The two were ushered in without question to the star-studded affair. "You know what they want to prevent in an event like this?" Osterweil asks. "Fresh vomit!