It isn't that Adam Sandler's portrayal of Barry Egan was technically much of a stretch for the actor; the eternally adolescent comedian has made a career of playing eccentric characters who are dormant volcanoes of rage and frustration just waiting to boil over. What makes Sandler's performance in Punch Drunk Love so unique -- and, indeed, so astonishingly good -- is seeing him play that kind of character in the strange world of Paul Thomas Anderson. There's no safety net for Sandler here; he can't just start ad-libbing, come up with some half-assed joke and end a scene if he feels like it -- he's actually being directed in this movie, and you can see that not only can he take direction but he also seems to rather like it. Seeing Sandler being treated (and acting) like a grown-up for the first time in this strange tale of a salesman with seven overbearing sisters who falls in love with one of the sister's co-workers (Emily Watson) is truly a sight to behold -- and makes for an extremely pleasurable movie experience.
In the spring of 1988, Michael Keaton had us believing in the Ghost with the Most with his manic portrayal of a professional "bio-exorcist" in Tim Burton's bizarre and wonderful fantasy, Beetlejuice. Keaton had delivered top-notch comedic performances before (Night Shift, Mr. Mom), but his Betelgeuse was one for the books. So how strange was it to see Keaton follow up such a rollicking madcap supernatural tour de force later that summer with something like Clean and Sober, in which Keaton played a drug-addicted con artist who hides out in a detox clinic to escape some thugs who want him dead, only to discover that not only does he have a substance abuse problem but that he can beat it? Keaton brought his trademark intensity to a dramatic role for the first time and pulled it off just as expertly as he did with haunting the poor Deetzes.
The girl who pretended (pretty successfully) to be a boy from Boys Don't Cry as a 1940s femme fatale? Brian De Palma's bit of stunt casting for The Black Dahlia actually worked because 1) Hilary Swank is, after all, a damn good actor and 2) wow, she is pretty hot! The Black Dahlia was not De Palma's finest work… in fact, it was pretty much one big hot mess (James Ellroy deserves much, much better), but Swank kept us watching with her fierce, sexy portrayal of one messed-up cuckoo bird who's sleeping with (and conning) half of L.A., including members of her immediate family. Of course it would all come to a bloody end in a sleazy hotel room with Josh Hartnett and a gun, wouldn't it?
Woody the kind, clueless bartender from Cheers as a psychopathic yet hopelessly romantic mass murderer? Director Oliver Stone told Woody Harrelson that he wanted him to play Mickey Knox in Natural Born Killers because he saw "violence" in him, and once NBK was unleashed, we became true believers. The fact that Juliette Lewis was so good as Mickey's paramour and partner in crime, Mallory Knox, was no surprise, as she'd already made a career of playing crazy, angry white trash by 1994, but the only thing we'd really seen Woody do post-Cheers was play basketball with Wesley Snipes. There is no one else who could've played Mickey Knox, and Harrelson has never gotten another role since that has challenged him and allowed him to strut his stuff in the same way.
Both Jake Gyllenhaal and the late Heath Ledger had triumphed in several respective challenging roles before they were cast in Ang Lee's Brokeback Mountain, but no one could've expected these two would do so well as "gay cowboys" -- or, indeed, that they would be even cast as "gay cowboys." Both Jake and Heath give career-best performances in this film, which itself did wonders in addressing various stereotypes and stomping them into the dirt. Ultimately, no matter the details or circumstances, Brokeback Mountain was a love story, one told and performed with grace and passion -- and both Jake and Heath had plenty of that.