12. The Royal Tenenbaums (2001)
Tomatometer: 80%

What, you thought Rushmore was quirky? Sucker. With his next movie, Wes Anderson proved that was just a warm-up act: The Royal Tenenbaums takes offbeat character studies to a whole new level, making the Coen brothers seem like staid conformists in comparison. Here, Anderson takes an unwieldy cast -- including Gene Hackman, Anjelica Huston, Ben Stiller, Gwyneth Paltrow, Danny Glover, Luke and Owen Wilson, and, of course, Bill Murray -- and wrangles them into a suitably convoluted plot involving the scheming patriarch of the oddball Tenenbaum clan. As cuckolded neurologist Raleigh St. Clair, Murray doesn't carry a great deal of the film's weight on his shoulders, but one could argue that his typically subtle performance (summed up beautifully in the scene where he learns of his wife's various marital transgressions) helps anchor a movie constantly in danger of floating right off the rails. It wasn't a huge hit at the box office, but like Rushmore, it enjoyed largely positive reviews and has continued to build a following on the home market. Although critics had their issues with Tenenbaums, most of them agreed with the Chicago Reader's Jonathan Rosenbaum, who said "Whatever my qualms, it's still one of the funniest comedies around."

11. What About Bob? (1991)
Tomatometer: 81%

Bill Murray has always excelled at playing unflappable slackers, while nobody can handle the role of an uptight fussbudget with quite the aplomb of Richard Dreyfuss -- which meant that pitting them against each other in 1991's What About Bob? was virtually a guarantee of critical and commercial success. Fortunately for fans of progressively over-the-top comedy, the movie basically delivered on that guarantee -- although it's perhaps not as consistently hilarious as some of Murray's truly classic comedies, it went down as easily one of the funniest films of the year. What About Bob? boasts some of Frank Oz's lightest direction, which is truly saying something, but it makes sense; all he had to do, really, was let the cameras -- and Murray and Dreyfuss -- run with their characters. Murray's Bob is a well-meaning soul whose many phobias prevents him from living a normal life -- or from allowing his psychiatrist to take the vacation he's been craving. As that psychiatrist, Dreyfuss is at his sputtering, bug-eyed best, and together, the duo transcends what was by then already a very tired plot (and, it must be said, a patently ridiculous final act). What it boils down to is a very funny film -- one, in the words of FulvueDrive-in's Chuck O'Leary, "made even more amusing by the fact that Murray and Dreyfuss couldn't stand each other in real life."

10. Quick Change (1990)
Tomatometer: 84%

Bill Murray as a burned-out bureaucrat who disguises himself as a clown to lead a motley crew on a bank robbery -- only to find his escape blocked by a seemingly endless series of mishaps delivered by the gridlock and innumerable misfits of New York City. Even now, Quick Change's synopsis sounds like a surefire recipe for box office success, but in spite of mostly positive reviews, Murray's (co-)directorial debut went down as one of 1990's highest-profile flops, grossing less than $16 million during its theatrical run. It isn't a particularly ambitious film (Steve Crum of Dispatch-Tribune Newspapers summed it up as "funny fluff"), and most critics agreed that it doesn't boast one of Murray's finest performances, but Quick Change has held up well thanks to a stellar supporting cast that the filmmakers had the good sense to highlight, including Jason Robards, Phil Hartman, Stanley Tucci, and Tony Shalhoub (the latter two would go on to star together in the critically acclaimed, and equally box office-starved, Big Night). Murray stepped behind the camera for Quick Change after he and screenwriter Howard Franklin, who worked from Jay Cronley's book, decided they were too close to the material to hand it over to anyone else -- but it would seem that what Murray really wants to do is not direct: this remains his sole directorial credit.