9. Rushmore (1998)
Tomatometer: 86%

The second act of Murray's career, in which he pivots from playing sleepy-eyed shysters into more finely nuanced dramatic roles, starts with this film, which broke director Wes Anderson through to a larger audience, essentially redefined the quirky high school movie for a new generation and reaped scores of awards and nominations for its trouble. Though it was never anything close to a box office hit -- its gross stalled at just over $17 million, below its $20 million budget -- Rushmore has grown into a certified cult classic. The movie rests on Schwartzman's shoulders, and a good deal of the critical acclaim rightly centered on his turn as the troubled Max Fischer -- but for a not-inconsiderable number of critics, Murray's performance as the dissatisfied executive who befriends, then spars with Schwartzman was a revelation. While lauding Schwartzman as "the best underdog since Cusack in Better Off Dead," eFilmCritic's Brian McKay saved his highest praise for Murray, deeming this "the finest, funniest, and most deadpan performance of his career."

8. Broken Flowers (2005)
Tomatometer: 86%

By this point, Murray was becoming just as famous for his hard-to-decipher real-life antics as he was for anything he did on screen -- at least partly because anyone who wanted to hire him had no agent or manager to go through, and was forced to deal directly with Murray, supposedly through an oft-neglected personal voicemail box. True to form, for Broken Flowers -- and a part which director Jim Jarmusch said he wrote more or less specifically for his star -- Murray agreed to sign on only if he could stay within 60 miles of his home. Ironically, Flowers is a movie about traveling -- Murray's character visits former flames in an effort to determine which one sent him an anonymous letter informing him of the nearly 20-year-old product of their relationship. As much as his character spent the film in motion, Murray kept his performance close to home, delivering a quiet, minimalistic turn not terribly dissimilar from his work in Lost in Translation. The similarity was noted by more than one critic, and although Flowers didn't attract the same sort of attention as Translation, but most scribes agreed with Sight and Sound's Liese Spencer, who noted, "After a career of deadpanning, Murray's impassive performance is still fresh, funny, sympathetic and restrained."

7. Tootsie (1982)
Tomatometer: 87%

It's got Stephen Bishop on the soundtrack and it takes place during an era in which soap opera stars had a somewhat realistic chance of appearing on the cover of mainstream publications -- but despite these anachronisms, Tootsie remains largely as fresh and funny as it was in 1982. And although it would be at best misguided to give Bill Murray a large portion of the credit for this, his scene-stealing, unbilled turn as Dustin Hoffman's playwright roommate did give a terrific early indication of Murray's willingness -- eagerness, even -- to take on smaller roles in the right projects. It's easy to see why Murray might have wanted to show up and film a few days of Tootsie, too: with Dustin Hoffman in the lead, Sydney Pollack behind the cameras, and a script whose writers included Barry Levinson and Elaine May, it was a pretty sweet gig whether or not your name ended up above the title. As an added bonus, the movie's examination of gender roles fit perfectly with the times, helping propel Tootsie to nearly $175 million in receipts and plenty of glowing reviews from critics like Emanuel Levy, who called it "one of the best and most significant comedies of the 1980s."