Best Actor, 1968, Charly
Robertson died in 2011, and achieved a real boost in fame during his last decade from fondly co-starring as Uncle Ben in the Tobey Maguire Spider-Man films. Before that, his resume doesn’t look much like one belonging to a Best Actor winner, who beat Peter O’Toole in one of his finest roles (as Henry II in The Lion in Winter) for playing a baker with learning disabilities in Charly, Ralph Nelson’s whimsical, largely forgotten tearjerker. It was a controversial win even then: Time magazine ran a piece about “the excessive and vulgar solicitation of votes” and singled out Robertson’s performance as overpromoted. Ouch.
Before the Oscar, he played a lot of soldiers and did some good television, in stuff like The Twilight Zone; after it, besides playing Confederate guerrilla Cole Younger in Philip Kaufman’s The Great Northfield Minnesota Raid (1972), the Jimmy Stewart role in Brian De Palma’s virtual Vertigo remake, Obsession (1976), Hugh Hefner in Bob Fosse’s Star 80 (1983) and the US president in Escape from L.A. (1996), it was a patchy career which never lived up to the potential suggested by his .
3. Cuba Gooding, Jr
Best Supporting Actor, 1996, Jerry Maguire
“Show me the money!”, Gooding’s Rod Tidwell forces Tom Cruise to scream down the phone in Jerry Maguire. Never has a catchphrase so tragically encapsulated an Oscar-winner’s subsequent career. Gooding was a visible star before this, thanks to his lead role in John Singleton’s wonderful Boyz N the Hood (1991) and support in the likes of hits A Few Good Men (1992) and Outbreak (1995).
Alas, things went so instantly wrong, post-Maguire, that to read his subsequent CV is to imagine a vivid procession of sacked agents begging, nay screaming, for one last chance. He was the Virgil to Robin Williams’s Dante in the afterlife schmaltz-fest What Dreams May Come (1998); a shrink in the ridiculous Instinct (1999); a wisecracking ice-cream delivery guy in the bio-warfare bomb thriller Chill Factor (1999). After accidentally checking onto a gay cruise and having to fend off Roger Moore’s advances in Boat Trip (2002), one of the worst-reviewed films of all time, and playing a Miami dentist who inherits a husky team in the same year’s Snow Dogs, things were really on the slide.
That’s even before al fresco sex with fellow assassin Helen Mirren in Lee Daniels's insane Shadowboxer (2005), standing in for Eddie Murphy in Daddy Day Camp (2007), and indeed co-starring with him in Norbit (2007). Still, small roles in The Butler and, not to mention his starring role as OJ Simpson in Ryan Murphy's TV series American Crime Story, suggest that a Gooding comeback could easily be in the offing
4. Louise Fletcher
Best Actress, 1975, One Flew Over the Cuckoo’s Nest
Is it unkind to call Louise Fletcher’s Oscar a bit of a fluke? Memorable though she is as Nurse Ratched, it took one of the all-time weirdest Best Actress fields to complete Cuckoo’s Nest’s full house of major Oscar wins. Fletcher had been raising two sons, and had barely worked for 10 years before that role, outside a supporting part in Altman’s Thieves Like Us (1974) (she lost a part in his Nashville, to Lily Tomlin). She wouldn’t have stood a chance against a Faye Dunaway, Jane Fonda or Ellen Burstyn vehicle that year (such was the paucity of prestige contenders, they even nominated Ann-Margret in The Who’s rock opera, Tommy).
Still, everyone warmed to Fletcher’s victory when she thanked her deaf parents using sign language, and she won for what is definitely her best performance.
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