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10. "Fear and Loathing in Las Vegas" (1998)
Playing a still-living real person (or at least a fictionalized version of him) is no easy task, but Depp's colorful portrayal of gonzo journalist (and walking pharmacy) Hunter S. Thompson proved that actors can be matched perfectly with certain material. In fact, Depp is reprising the role (basically) in this month's "The Rum Diary." With faux baldspot, ubiquitous cigarette and clenched-jaw drawl, Depp -- and lawyer-sidekick Bencio del Toro -- drifts through "Loathing's" modern-day Bacchanalia of mind-altering substances and deranged characters under the loose, hallucinatory direction of Terry Gilliam. Depp later re-teamed with Gilliam to play an alternate version of the late Heath Ledger in "The Imaginarium of Dr. Parnassus," but "Loathing" pushed Depp to the extremes of "Bat Country" unlike any of his previous films.
- Dave Lewis