BILL MURRAY AS JEFF SLATER IN TOOTSIE (1982)



Bill Murray is one of those people with such a long, varied career of starring and supporting roles in so many beloved mainstream and indie films -- from Carl Spackler in Caddyshack to “Bill Murray” in Coffee and Cigarettes -- that he could easily fill up this week’s list almost single-handedly. But of all his roles, his understated, largely improvised performance in Tootsie has always been my favorite: a toned-down version of his cocky '80s persona that hinted at the bemused, melancholy range of his later work, his Jeff Slater is the perfect roommate and wing-man: a wise, mellow pal who gently informs you when you’re "getting into a weird area" with your career or social life, yet who doesn’t scold or judge when he walks in to find you in a dress being groped by a horny old soap opera star. The yin to Dustin Hoffman’s neurotic actor yang, he’s the kind of playwright who’d prefer a half-empty theater filled with people who just came out of the rain to a packed house (and yet somehow doesn’t sound pretentious saying it).  And best of all, I actually got to have a roommate very much like him once (hi, Hari!), during a year I still recall as fondly as my memories of Tootsie and the late, great Sydney Pollack.  ("You were a tomato!")  (AO)

MICHAEL KEATON AS BEETLEJUICE IN BEETLEJUICE (1988)



Keaton made this movie with the director Tim Burton at a time when Burton had more experience working with cartoon characters than live actors. It was a sweet gesture on Keaton's part to meet him more than halfway. At the time, Keaton was six years past his impressive movie debut in Night Shift (as a pimp who operated out of a morgue and preferred to be called a "love broker") and overdue to take his career to another level, but even those who guessed that he had untapped potential couldn't have guessed that maggoty would be such a great look for him. Few actors have turned themselves into a special effect with such happy results. (PN)

KEVIN KLINE AS OTTO WEST IN A FISH CALLED WANDA (1988)



It’s a testament to John Cleese’s generosity as a comic author that he gave the absolute best role in A Fish Called Wanda to someone else. That someone else was Kevin Kline, who, in a performance he’d never again equal, took the ball and ran with it: his grasp on the character of Otto West, a short-tempered, virile, violent, and not altogether bright criminal and Ugly American par excellence is vice-tight. The great thing about Otto is that he’s not a typical dumb goon: he’s a fairly skillful criminal, a stone cold killer, and best of all, he’s very slightly aware of how dumb he is. While most stupid characters milk comedy out of their obliviousness, the genius of Otto’s stupidity (and Kline’s astute assessment of same) is that he knows he’s not the brightest bulb on the marquee, and it drives him crazy. Hence his one great taboo – he can’t stand it when people call him stupid. What’s more, Kline milks gallons of comic frustration out of Otto’s inability to wrap his head around complex problems; he’s never angrier than when he senses someone has the advantage of him, but since he’s not smart enough to fake it, he just gets angrier (and stupider). One of the best throwaway gags in A Fish Called Wanda comes when an elaborate plan starts to go awry and Otto is called upon to help think of a solution; obviously infuriated, he pointlessly fires a couple of rounds from his silenced pistol into a steel safe and bellows “I’m THINKING!”.  (LP) 

STEVE ZAHN AS GLENN MICHAELS IN OUT OF SIGHT (1998)



Steve Zahn specializes in characters who have a negative genius for being in the wrong place at the wrong time; in That Thing You Do!, things got dramatic while he was off enjoying a rollercoaster ride. Here, he takes it so far that he barely seems to be in the right movie, though you're glad he stopped by. After arriving to help bust George Clooney out of prison -- a favor for which Clooney thanks him by threatening to throw his sunglasses "off the overpass while they're still on your head" -- he hooks up with Don Cheadle's mob just in time to participate in a massacre that soon has him sneaking around in search of the back exit. If all petty criminals were more like Zahn's Glenn, the world would be a much more entertaining place, and practically a crime-free one. (PN)

JEFF BRIDGES AS JEFFREY “THE DUDE” LEBOWSKI IN THE BIG LEBOWSKI (1998)



Although he’s not the most clownish figure in the Coen Brothers’ endlessly quotable cult comedy – that title belongs to gun-toting, dog-sitting Vietnam vet Walter Sobchak, played with gusto by John Goodman – you’d be hard-pressed to find a figure more hilariously suited to the archetype of the Holy Fool than Jeff Bridges’ Dude. Conceived as a stoner upturning of Raymond Chandler’s hard-nosed detective Philip Marlowe, the Dude, a perpetually out-of-it former roadie whose life revolves around bowling, weed, and White Russians, is caught up in a web of mistaken identity, kidnapping and blackmail. While Marlowe stubbornly refused to be warned off a case, doggedly pursuing the truth for its own sake, the Dude barely even seems to be aware that he’s on a case, and yet, in his own shambolic, shaggy-dog way, has the instincts and aptitude of a real detective. Based on film promoter and ex-‘60s radical Jeff Dowd, the Dude is an immortal comic creation, a stumbling bum who outwits people more or less by default and lives in the sunshiney flipside of Los Angeles noir. His mind is never far from his next frame, and his dress sense isn’t quite tailored suits and ties, but let’s see Philip Marlowe disarm a rival simply by saying “Well, that’s just, like, your opinion, man.” (LP)

Click Here For Part One, Two, Three, Four, Five, Six & Eight

Contributors: Andrew Osborne, Phil Nugent, Leonard Pierce