Cloud Atlas

"Cloud Atlas" (2012)
Actor: Almost all of the principal cast take multiple roles. Tom Hanks, Halle Berry, Hugo Weaving, Jim Sturgess and Hugh Grant all feature in all six of the film's storylines as different characters in each, while Jim Broadbent, Doona Bae, Ben Whishaw, James D'Arcy, Zhou Xun, Keith David, David Gyasi and Susan Sarandon play at least three each.
Characters: They're a pretty diverse bunch of roles: Hanks goes from a mad ginger-bearded doctor to a poorly-accented Irish hoodlum, Broadbent is both a sea captain and a Korean musician, and Weaving plays sinister devil figure Old Georgie and a female, Nurse Ratchet-esque villain.
"Cloud Atlas" was always going to be one of the most ambitious films of recent memory: the adaptation of David Mitchell's bestseller had three directors, in Lana and Andy Wachowski and Tom Tykwer, it had a sprawling cast, a story that spanned thousands of years and multiple genres, and a three-hour running time. So it's no surprise that it's one of the most divisive: when it premiered two years ago, it was hailed simultaneously as both a masterpiece and a train wreck. The truth, as with so many cases, lies somewhere in between. The film is occasionally rubbish, and inconsistently acted (if Jim Sturgess has never been particularly good at playing one character, why would he be better as six?), and adds a slightly sappy destined-to-be-together subtext onto the novel. But it's also bold, beautifully made, incredibly well acted, consistently surprising, and always hugely engaging. The film does attempt to make its multi-cast form its substance, to some degree, but particularly given Lana Wachowski's involvement, making a film about how our bodies don't define our souls feels deeply felt and very personal. A bit of a mess, then, but a hugely compelling one.

Joe vs The Volcano Ryan

Joe Versus The Volcano” (1990)
Actor: Meg Ryan
Characters: Dede, Angelica, Patricia
It was loving writer/director John Patrick Shanley’s “Doubt” as much as we did that made us go back and relook at his only other directorial feature, the seemingly-couldn’t-be-more-different famed flop “Joe Versus the Volcano.” And while we’re hardly going to go as far as some revisionist critics in claiming it as neglected genius or anything, it certainly is a whole lot better that its initial reputation suggested. It starts very promisingly too, with a stylized, “Brazil”-esque imagining of the dehumanizing effects of wage slavery, before the titular Joe discovers he’s dying and finds a novel way to commit suicide, meeting three women successively along the way, all played by Ryan. Ironically for the purposes of this feature, one of the issues with the film seems to be its miscasting, which contributes to the unsettled tone of the endeavor which tries and fails to meld the sappy romance we’d expect of a Hanks/Ryan film from this era, with the fairly caustic and pessimistic wit of Shanley’s script. And Ryan, certainly at this stage more a light comedienne than an actress of great range or depth, struggles to convince in her triple role, with both of the early characters coming across as rather one note until the more rounded Patricia (still rather too odd and prickly a character to sit comfortably with the actress) takes over as primary love interest. By no means an unqualified success, the film’s ambition and hidden intelligence, along with an unusually philosophical bent, make it about ten times more interesting than the standard Hollywood romcom that it was marketed as, and isn’t. 

The Life and Death of Colonel Blimp kerr

"The Life And Death Of Colonel Blimp" (1943)
Actor: Deborah Kerr
Characters: Edith Hunter, Barbara Wynne, Angela "Johnny" Cannon
The first of Powell & Pressburger's multiple masterpieces (read more about them here), "The Life & Death of Colonel Blimp" is an extraordinary end-of-Empire masterpiece that follows Roger Livesey's army lifer Major-General Clive Wynne-Candy from his youth in the Boer War through the Great War, to old age and semi-retirement during the (then-still-ongoing) Second World War. The film is expansive and multi-faceted, primarily focused on the passing of time, of good soldiers and bad wars, and on the demise of England as past generations had known it, replaced by the birth of something new. But as ever, Powell & Pressburger have a romantic streak a mile wide, and that's represented in the three roles played by Archers' favorite Deborah Kerr here. The one that perpetually got away, she's initially Edith, a British woman whom Clive falls for, but who becomes engaged to his German friend Theo (Anton Walbrook); then her doppelganger Barbara, a young nurse in the First World War (who dies offscreen in the 1930s); and then, in the then-present-day, a sparky young driver nicknamed Johnny. Kerr has no prosthetics or anything to distinguish the three, but subtly modulates each one so that they feel truly like women of their era, and few would blame Livesey's character for being haunted by her. The heartbreaking reveal that she's involved with his rival, Spud Wilson, near the end is one of the many ways that Powell & Pressburger show how the 1940s have brought a changing of the guard, with a brasher, more ruthless brand of soldier replacing the more gentlemanly Wynn-Candy. "The Life And Death Of Colonel Blimp" is a film positively bursting with soul, but much of it comes from Kerr's trio of performances.