Edward Scissorhands (1990)This is where it all started – the year the kid from Jump Street became a movie star, with lead roles in Tim Burton's divinely sweet fable about a boy with shears for fingers, and in John Waters's camp romance Cry-Baby. What Scissorhands has going for it, though, is a brilliant story, a delicate performance by Depp, and the deliciousness of knowing that Depp and costar Winona Ryder were a real-life item (and the prime example of why you don't get your girlfriend's name permanently inked on your bod).
Best scene: Edward finds his professional calling as the go-to avant-garde haircutter of suburbia, snipping the locals' stuffy styles into au courant coiffures. For a while, anyway, he finds a home.
Moviestore Collection / REX USA
Pirates of the Caribbean: The Curse of the Black Pearl (2003)If Edward Scissorhands is where Depp started using makeup and costumes to hide behind his characters, then Pirates is where he does it at his waggish, saucy best. Capt. Jack Sparrow may be a cliché now – your best friend's sister's boyfriend's go-to Halloween costume – but he was a bold, ballsy surprise a mere 10 years ago.
Best scene: Jack is at his most roguishly charming before you get used to him – or, God forbid, grow tired of him. So the best scene has to be the one in which we meet him, sailing his sinking ship into the harbor, only to step off the crow's nest and onto the dock, wherein he immediately skirts the law and steals a purse.
Donnie Brasco (1997)Depp dropped the masks and the makeup to play a man who hides in plain sight – Donnie Brasco, a.k.a., FBI agent Joe Pistone – in one of his most overlooked roles. It's understandable that Depp was sidestepped for Oscar consideration that year, since names like Fonda, Duvall, Damon, Nicholson and Hoffman were in contention. But it's still a shame, given how assured and comfortable Depp's performance was as a deep-cover mob infiltrator.
Best scene: Depp convinces Al Pacino's Lefty Ruggiero that he can be trusted by telling the wiseguy that the diamond he's trying to sell is a fake. The kicker is the little smile Donnie/Joe flashes when he realizes Lefty is buying his act – just a touch too much confidence from a guy in serious danger.
Industrial Light & Magic
Rango (2011)I've never been a huge fan of Depp's Hunter S. Thompson obsession (which means Fear and Loathing in Las Vegas and The Rum Diary were both somewhat lost on me). But animation seems like a dandy place for a persona that over the top, which is one of the reasons I find more to like about Rango every time I watch it. The movie didn't go over terribly well with the small set (it is about water rights in arid municipalities, after all), but there are plenty of sly jokes and wonderful voice acting from Depp.
Best scene: Rango blunders into the town saloon, then suddenly realizes that he can completely reinvent himself as a rascal from the west, “from everywhere there's trouble brewing and hell waiting to be raised.” A hero is born.
Before Night Falls (2000)Depp actually has two roles in the film about Cuban dissident poet Reinaldo Arenas (Javier Bardem, Oscar nominated for the role), but only a few minutes of screen time. He's terrifically twisted as prison warden Lt. Victor, but he completely steals his scenes as Bon Bon, a prison fixture who cross-dresses, spreading delight as much as she can in the repressive regime. It can be frustrating watching Depp duck behind disguises in film after film, but here it works on two levels: as a way for him to play with another kind of character and as an act of defiance for the transgressive transvestite.
Best scene: Bon Bon, in her enormous capacity for, um, let's call it kindness (not to mention bravery), smuggles Arenas's manuscript out of prison, ensuring that his work will get out, even if, perhaps, he never does.