Bill Murray's Wackiest Moments

Comedian Will Ferrell takes a dramatic turn as a depressed alcoholic in Everything Must Go. Jennie Yabroff discovers what makes this happy man the saddest.

Bill Crashes Karaoke Night

He may not have had Scarlett as his sidekick this time, but Bill Murray almost reenacted that memorable scene from Lost in Translation when he showed up recently at New York City's Karaoke One 7 with another charming female companion The notoriously social funnyman announced all drinks were on him, before belting out Elvis' "Marie's the Name" to the crowd's delight. After a 35-year acting career, maybe all Bill really wants to do is sing.

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Bill Stiffs a Cabbie

The man is certainly unpredictable: The Rushmore star took one chauffeur on a joyride after last year's Sundance Film Festival, racking up a $200 fare that he then didn't have enough cash to pay for. After his credit card was denied, he promised to mail the driver a check for what he didn't have on hand. Though you may have guessed it (or not), Bill kept his word, and even added a generous tip.

Bill Bartends

If you happened to pop into Shangri-La during last spring's South by Southwest festivities, you might have seen the Ghostbuster pouring tequila shots with other bartenders. He sidled up to the bar amidst throngs of concertgoers and attempted to momentarily blend in with the group, then snuck behind the counter and started mixing cocktails. But he wasn't very accommodating to drink requests. Bill only gave out shots of tequila that night.

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Bill Hangs with MGMT

Imagine you're at a Halloween party dressed as Carl, the hilariously weird groundskeeper hell-bent on blowing up a gopher in the comedy classic Caddyshack, only to see the movie's funniest oddball in the flesh. Such was the case for one guest of a late-night Halloween bash in East Williamsburg in 2008, when Bill Murray showed up as himself, tapped the keg, and then tore up the dance floor. Later that night, he was seen gallivanting with Brooklyn's favorite hipster duo band, MGMT.

Getty Images; AP Photo

Bill Woos the Ladies

He's sure got a way with women. A month after crashing the Halloween party in '08, Bill was spotted dining at Chicago's hot spot Sepia with then-27-year-old Crystle Stewart, 2008's Miss USA. In the wake of his divorce that year, onlookers noted that he seemed cheered by Miss Stewart's presence. After dinner, he affectionately embraced a cluster of female fans outside the restaurant.

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Bill Drinks and Drives…a Golf Cart

In August 2007, the eccentric star decided it would be a good idea to drink and drive around the streets of Stockholm not in a car, but a golf cart. According to a Stockholm detective, Murray did not want to use their breathalyzer testing instrument and told the officer that in America it wasn't necessary to do a breath test. While he is no lawyer, Murray was able to sneak out of some serious charges. He later signed a statement that said he had been drinking while he was in Sweden for a golf tournament, and had a police officer plead guilty for him while he traveled back to the States.

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Bill Terrorizes the PGA Tour

Only Bill Murray could transform a professional PGA golf tournament into a slapstick comedy routine. At the 2006 AT&T Pebble Beach National Pro-Am in California, Murray kicked off the tournament with a few zingers. He did the old "Did you spill something on your shirt?" routine to a 16-year-old fan and was able to bop her on the nose, which raised a few chuckles. But by the 12th hole, Murray grabbed a Bloody Mary from a house near the golf course, and at the next hole handed the half-drunk beverage to a female spectator, asking her to "polish that off will ya?" Later he threw a golf ball into the audience, chased a cameraman, and sat in an inflatable canoe. The only thing missing was a gopher.

Everett Collection

Bill Tries to KO Chevy Chase

Bill's boisterous attitude apparently has a long history. Murray replaced Chase during the second season of Saturday Night Live in 1976 after he left the show to pursue a movie career. But it was rumored that most of the SNL cast was glad to see him go—Chase was often referred to as "smug." When Chase returned as a guest host, Murray took it upon himself "as the new guy" to tell him he was disliked by the cast. Chase then told Murray that his acne-scarred face looked like "Neil Armstrong had landed on it." Murray tried to take a few jabs at Chase and also insinuated he needed to fuck his wife more. Yet all was forgiven in Hollywood. Four years later, the duo starred in Caddyshack together.