It's going to be difficult to top Cloud Atlas as the Multiple Role Masterpiece of our times as nearly everyone you see in the film - Tom Hanks, Halle Berry, Hugh Grant, Hugo Weaving, Jim Broadbent and Ben Whishaw - takes on a handful of multiple characters. You only think you catch them all. When the end credits highlight each actor's onscreen contribution, you'll be shocked by how often you failed to recognize Hugh Grant.
Before Tom Hanks took on a multiple role movie of his own with 'Cloud Atlas,' he witnessed co-star Meg Ryan give it a shot in Joe Versus the Volcano, where she played three different characters. While Hanks' many Cloud Atlas transformations required make-up and prosthetics, Ryan distinguished her trio of personalities using only wigs and good old-fashioned acting (not to dismiss actors who take the make-up route). It's quite clear which Meg Ryan is which even with the film on mute. Of course, it's the familiar blonde Meg Ryan that Joe falls in love with at the end.
Like 'Cloud Atlas,' Lost Highway doesn't utilize multiple role actors for novelty's sake but as part of the film's thematic through-line. The specifics of that thematic through-line, however, are up for debate. All we can say for sure is that this film has two Patricia Arquettes, one with blonde hair and one with black. There are enough Patricia Arquettes going around that both Bill Pullman and Balthazar Getty get one. Except Bill Pullman and Balthazar Getty are the same dude. So the two Patricia Arquettes are actually sharing them/him. I think. It's about the duality of man, Man.
You might think Army of Darkness is on this list because Bruce Campbell gets to play both Good and Evil Ash (like how the characters in 'Cloud Atlas' play both good and evil roles), but that's not it at all. No, despite Campbell's clear talents, Army of Darkness is a Multiple Role Masterpiece not for the two Ashes, but for the three Ted Raimi's.
Like with Bruce Campbell and that 1972 Oldsmobile Delta 88, no Sam Raimi film is complete without his brother Ted showing up somewhere. In Army of Darkness, Ted Raimi plays three different barely seen characters. One is a cowardly villager, one is a slightly less cowardly villager, and one is a fellow S-Mart employee Ash talks to near the film's end. Most people hardly recognize him in the film simply because most people don't know what he looks like.
No one has taken the Multiple Role tactic to heart more than Eddie Murphy. From his 'Nutty Professor' films to 'Norbit' to The Fatties to 'Vampire in Brooklyn,' Eddie Murphy is not shy about putting on tons of make up and playing against multiple versions of himself.
It's tired at this point, but back at the beginning Murphy's schtick was pure gold. Along with costar Arsenio Hall, Eddie Murphy fills Coming to America with many different racial caricatures making it one of the funniest films of the 1980s. The barbershop scene is a Multiple Role Masterpiece all by itself.
'Back to the Future, Part II'
We knew the Back to the Future series was into showing actors at different ages. The first film sported both young and old version of Lorraine Baines, Biff Tannen, and George McFly. So it seemed a no-brainer that Part 2's trip to the future would include elderly version of these characters as well.
What we maybe didn't expect was Michael J. Fox's turn as both his children: Marty McFly Jr. and Marlene McFly. As Marty Jr., Fox kind of plays a looser, dumber version of Marty Sr. But his portrayal of Marlene was accurate enough that boys all over the nation likely found themselves with very confusing crushes. (If I'm alone in this, please don't tell me.)
As the corrupt President Scroob and the mystical Schwartz master, Yogurt, Mel Brooks gets to portray both the most evil and most virtuous characters in his sweeping, epic Spaceballs universe. Brooks also played multiple characters in Blazing Saddles, clearly the more classic film, but the gulf between these two particular characters reveals the better multiple role example. Besides, little Yogurt is just way too adorable to discount.
Every Monty Python movie is a Multiple Role Masterpiece. Distributing a film's worth of roles across just handful of actors is a sketch comedy movie tradition, actually. And Python did it best. In Holy Grail, for instance, John Cleese gets to be Sir Lancelot, the Black Knight, the mean French guy, and Tim, the Enchanter. Those are four iconic character right there, and that's just one Python. Each member gets his fair share of awesome characters to play and knock out of the park.
Mike Myers' talent for writing jokes is surpassed only by his ability to run those jokes into the ground. But back when the whole Austin Powers thing was still a new surprise, Myers' portrayal of the swinging spy and his arch nemesis, Dr. Evil, seemed a stroke of Multiple Role genius. He'd already practiced the tactic once earlier in 1993's 'So I Married an Axe Murderer' so his success here wasn't that much of a surprise.
Myers would later take the novelty too far, adding Fat Bastard the 'The Spy Who Shagged Me' and Goldmember to 'Goldmember' and basically filling the sequels with too much of himself. But the original's double dip of Myers offered a perfect dose of his mugging and catchphrases.
'Diary of a Mad Black Woman'
Regardless of what you think of Tyler Perry as a person or a filmmaker, it's difficult to deny his success as a multiple role actor. Taking off from the precedent set by Eddie Murphy, Tyler Perry typically tackles three very distinctive roles in his Madea films. Obviously, there's Madea. But Perry also plays Joe, her pot smoking, lecherous brother, and Joe's son Brian, a mild-mannered lawyer who doesn't not require any special makeup and is therefore very boring.