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1. Eddie Murphy, Dreamgirls > Norbit
When Oscar prognosticators were laying odds for the 2007 Academy Awards, Eddie Murphy’s dynamic supporting performance in Dreamgirls, as an R&B superstar felled by personal demons, was far and away the category’s frontrunner. Here was a gifted yet reclusive performer, seemingly resigned to starring in lowbrow family comedies like Daddy Day Care and the Nutty Professor movies, who had finally bared his soul onscreen—and it was beautiful. Then Norbit happened, and the Oscar went to Alan Arkin in Little Miss Sunshine. Although Murphy’s surly public appearances did him no favors, the image of him in a grotesque fat suit and hot-pink bikini as Rasputia—a malevolent, flatulent Big Momma-type who terrorizes everyone she encounters—spurred his precipitous decline. (And if that wasn’t enough, his work as “Mr. Wong,” an Asian-American stereotype to rival Mickey Rooney in Breakfast At Tiffany’s, sealed the deal.) Murphy stormed out of the Oscar ceremony early that night, no doubt to comfort himself by cuddling a giant pile of money.
2. Jamie Foxx, Ray > Stealth
Jamie Foxx was the toast of Hollywood with his spot-on, Oscar-winning portrayal of Ray Charles and simultaneous Oscar nomination for a cabdriver in Collateral. (He was the first black actor to be nominated twice in the same year.) Having just completed the 14-year journey from unknown In Living Color comedian to pinnacle of screen success, Foxx opted to rapidly regress in a wasted role in the action-thriller Stealth, one of the biggest flops of all time, in which the actors take a back seat to a talking fighter jet. Foxx’s death by robo-plane—which achieved hyper-intelligence after being hit by lightning, no less—seemed to take his career down in the wreckage, as he hasn’t done anything even remotely nomination-worthy since. His Rain Man-esque turn in The Soloist seems like a conscious grab at Oscar respectability after a few years in the desert.
3. Anne Hathaway, Rachel Getting Married > Bride Wars
To be fair, Anne Hathaway was best-known for light, tween-girl-friendly comedies like The Princess Diaries, Ella Enchanted, and The Devil Wears Prada prior to her revelatory, Oscar-nominated performance as a recovering drug addict in Jonathan Demme’s jittery melodrama Rachel Getting Married. It probably seemed like a good idea at the time—career insurance, really—to book another lighthearted chick-flick to come out right on the heels of her adventures in indie-land. Still, Hathaway could’ve read the Bride Wars script a little more closely, just to realize she was about to follow a nuanced, funny, heartrending film about sisterly devotion with a shrill, hateful farce about wedding-crazy harpies. Bride Wars may not ultimately set Hathaway’s career back much, but it’s done some heavy damage to womankind.
4. Steven Spielberg, Munich > Indiana Jones And The Kingdom Of The Crystal Skull
Spielberg has made a ton of films, but Munich is the most controversial and the most polarizing. Taking a look at a historical tragedy beyond dispute, Munich then called into question the “eye for an eye” mentality of human nature, with strong implications about the current war on terrorism. Oscar-nominated for his unusual thoughtfulness, Spielberg turned around and made another polarizing film, in which the controversy was, “How much should the plot focus on aliens?” No one wanted Spielberg to make Indiana Jones as somber and reflective as Munich, but they also didn’t want him to wind up the franchise on a bad note. The two films could be held up as textbook cases of, respectively, a film where the director wanted to say something, and a film a director made just to make it.
5. Tom Hanks, Saving Private Ryan > You've Got Mail
At this point, Tom Hanks’ name is all but synonymous with “overblown, middlebrow prestige fare”; unlike many of the people on this list, he’s maintained a fairly even keel throughout his career, not so much veering from quality to crap as focusing on a particular kind of expensive, high-polish, tasteful-prestige-picture crap, from Sleepless In Seattle to Forrest Gump to The Polar Express to Cast Away and beyond. Still, there's a fairly noticeable drop-off between his Oscar-nominated role in the emotionally wringing, exhaustingly ambitious World War II picture Saving Private Ryan and his immediate follow-up in the schmaltzy, pandering Norah Ephron Shop Around The Corner remake You’ve Got Mail. From grit and glory to smarm and cutesy in the same year, and without ever changing that pinched, vaguely strained expression… that's Tom Hanks’ career in a nutshell. Well, that and vast heaps of money.
6-7. Kate Winslet and Jackie Earle Haley, Little Children > All The King’s Men
The duo who most stood out from the strong ensemble cast of Little Children—earning Best Actress and Best Supporting Actor nods—ended up on another ensemble cast the next year, for the second film adaptation of Robert Penn Warren’s All The King’s Men. The film was a complete flop, mostly because, for all the stars crammed into the cast, most didn’t have enough space to work. Winslet, an opponent and eventual mistress of Sean Penn’s Huey Long, is used as a bland stereotype of Southern aristocracy, while Jackie Earle Haley is cast as Penn’s taciturn bodyguard. In the book, Haley’s character is a stuttering, devoted admirer, but the film’s version could have been played by an extra—an example of what’s wrong throughout. Maybe Winslet and Haley would have opted out if they had known how much All The King’s Men was going to be about the king.
8. Terrance Howard, Hustle & Flow > Four Brothers
There's some argument to be made that Terrance Howard’s performance in the already badly aging Hustle & Flow wasn’t terribly great, but at least the movie had a reasonably compelling story: Pimp becomes rap star by writing about his own life. He stood virtually no chance of winning, given the competition that year—Heath Ledger, Joaquin Phoenix, David Strathairn, and winner Philip Seymour Hoffman—but at least he was in lofty company. Instead of building on that goodwill, Howard wound up in John Singleton’s borderline-retarded Four Brothers, about four unrelated dudes (Mark Wahlberg! Andre 3000! Tyrese! Um… Garret Hedlund!) who discover that their adoptive mother’s death wasn’t a botched robbery, but rather a murder perpetrated by some sort of badly defined underworld characters. Howard pops in as the brothers’ potential savior, a cop who tells it like it is, then dies before he can expose the truth: that this was a shitty, shitty movie.
9. Felicity Huffman, Transamerica > Georgia Rule
Transamerica proved that at least someone on Desperate Housewives could act; Georgia Rule proved that there are far worse forms of femintertainment than Desperate Housewives. Huffman plays the mom of Lindsay Lohan (who, as a sex- and booze-crazed teenager, basically plays herself) and daughter of blue-blood über-Christian Jane Fonda, forming a generational trifecta of boring. In Transamerica, Huffman got a lot of mileage out of unconventional, sometimes uncomfortable, sexual topics; in Georgia Rule, sexual abuse of a minor is used as a lazy plot device. The only convincing thing Huffman does in the film is drink excessively; perhaps, given the film around her, that part didn’t take too much acting.
10. Denzel Washington, Training Day > John Q
After winning an Oscar for his portrayal of a pistol-waving, angry criminal-cop in Training Day, Denzel Washington opted to play a pistol-waving, angry criminal-parent-of-a-child-with-an-enlarged-heart in John Q. Not surprisingly, watching Washington antagonize police newbie Ethan Hawke with a mindfuck of violence, drugs, and corruption turned out to be a lot more interesting than watching Washington antagonize police veteran Robert Duvall with a non-mindfuck of clichéd hostage games. But hey, even DW is allowed a movie off every now and then; sure, his John Q perfectly fits Hollywood's sympathetic-hostage-taker stereotype, but even Duvall and mean-cop Ray Liotta basically give half-assed reprisals of their characters from Falling Down and Cop Land, respectively.
11. Alec Baldwin, The Cooler > The Cat In The Hat
Don’t remember the mean next-door neighbor in Dr. Seuss’ The Cat In The Hat who tries to marry the kids’ mom and send the boy away to military school? Well, Alec Baldwin’s character, which was added to the film version, surely wasn’t memorable. In that and The Cooler, Baldwin plays a somewhat seedy individual trapped in an unusual world, but the dying universe of Las Vegas’ gritty underbelly turned out to be a lot more captivating than the bonkers, slime-covered alternate dimension of The Cat In The Hat. As a repulsive, unemployed schmuck with nothing better to do than watch strippers on TV and harass children, Baldwin is easy to dislike in The Cat In The Hat—too bad, considering the best thing about Baldwin’s old-Vegas, hard-line casino boss was how hard he was to dislike. He earned a Best Supporting Actor nomination for his Cooler role, though he lost to Tim Robbins for Mystic River.
12. Renée Zellweger, Cold Mountain > Bridget Jones: The Edge Of Reason
Zellweger won a Best Supporting Actress Oscar for her no-nonsense, poor land-working Southerner in Cold Mountain, adding a sympathetic personality to the rough reality of life during the Civil War. Rescuing a failing farm with her bare hands is a fine feat, for sure, but not one likely to draw the date-movie hordes like rescuing a failing relationship with her fake British accent. That required Bridget Jones: The Edge Of Reason, where Zellweger’s stint as the titular diary-writer wanders off into the silliness of sequel-land as she’s caught with cocaine in Thailand and becomes a human-rights celebrity while in prison. Truly operating from the outer edges of reason, Reason is a further reminder to actors that winning an Oscar allows them to choose roles rather than taking every sequel they’re pitched.
13. Hilary Swank, Million Dollar Baby > The Black Dahlia
With Million Dollar Baby (and its Best Actress Oscar), Swank proved once and for all that she could hold down a big-ticket film on her own. So it’s curious that she would allow her next project to be one with Josh Hartnett at the helm: Playing a rich, promiscuous socialite, Swank is the girlfriend in Hartnett’s love triangle who is supposed to—but in reality absolutely doesn’t—look like the spitting image of the titular victim. (It’s unclear why no other character sees the stark non-similarities.) To be fair, Swank probably was thinking Brian De Palma was crafting another L.A. Confidential, where even a bit role becomes part of a memorable, enjoyable whole. She was wrong.
14. Christopher Walken, Catch Me If You Can > Kangaroo Jack
Walken reminded the world he could still do heartfelt with an unexpectedly affecting portrayal of Leonardo DiCaprio’s concerned-but-loving father in Catch Me If You Can. He then immediately reminded the world that he can still do completely ridiculous, as an unloving mobster stepfather in Kangaroo Jack. Instead of trying to dissuade his son from a life of crime, Walken’s Kangaroo Jack character forces his stepson into one by transporting money to Australia, where a kangaroo steals it. Catch Me If You Can got him a Best Supporting Actor nomination; Kangaroo Jack got him a Worst Supporting Actor nomination at the Razzies. That said, most of the people who went to see the movie were probably less disappointed in Walken than in the fact that the kangaroo didn’t talk.
15. Jack Nicholson, About Schmidt > Anger Management
Nicholson has been in semi-retirement for more than a decade, emerging every year or two to take parts with some special meaning to him. He won an Academy Award for the 1997 James L. Brooks dramedy As Good As It Gets, then took four years off before appearing in Sean Penn’s bleak character sketch The Pledge. In 2002, Nicholson was nominated for a Best Actor Oscar again for a performance many considered a career high, playing a lonely retiree on a dispiriting road trip in About Schmidt. He then jumped straight into Anger Management, a shaggy Adam Sandler comedy in which Nicholson played an offbeat therapist teaching the repressed Sandler how to express himself appropriately. (Perhaps not coincidentally, Anger Management was also Sandler’s first major role since playing a similar character in Paul Thomas Anderson’s decidedly artier Punch-Drunk Love.) Nicholson has often expressed his admiration for physical comedians like Sandler and Jim Carrey, so perhaps it isn’t too surprising that he’d want to take a break from tough dramas and do something broad. Nevertheless, when the Academy prepares its “In Memoriam” clip reel for Nicholson someday, don’t expect a lot of footage of Nicholson and Sandler yelling at each other.
16. Djimon Hounsou, In America > Biker Boyz
Hounsou gave a startlingly touching performance in In America as a Nigerian artist lurking in New York’s impoverished underground, and he earned a Supporting Actor nomination in the process. His follow-up, Biker Boyz, kept the Africa theme alive (his name is “Motherland”) and moved him to the California underground… well, the underground world of motorcycle racing. Viewers hoping to see a repeat of his inspirational role as an AIDS-afflicted neighbor who gives hope to an immigrant family didn’t get it. Those viewers did, however, see him ride a motorcycle fast.
17. Gus Van Sant, Good Will Hunting > Psycho
The critical and commercial success (and Best Director nomination) of the sleeper hit Good Will Hunting gave indie-maverick-turned-A-list-big-shot Gus Van Sant the clout to get just about any project green-lit. Unfortunately, Van Sant had his heart set on a pointless remake of Psycho starring a bizarrely miscast Vince Vaughan as everybody’s favorite mama’s boy gone awry. The result was less an intriguing postmodern experiment than a leaden vanity project.
18. Rob Reiner, A Few Good Men > North
Rob Reiner’s A Few Good Men is in many ways the very definition of a prestige picture: adapted for the screen by Aaron Sorkin from his own successful stage play, tackling weighty issues about military and personal responsibility, and featuring A-List actors, including Jack Nicholson in a brief but meaty role. Reiner managed to snag a Best Picture nomination for the film, and while it didn’t win the prize, Men left him at a critical and commercial peak. Which is one of the many (many, many) reasons North is as painful as it is. A chintzy kid comedy suffering from an aggressively cute high-concept script, it isn’t the worst movie ever made, but it’s arguably the worst film Reiner’s done, and coming after a career highpoint, it landed with a resounding thud in multiplexes nationwide. Reiner learned his lesson, though, and teamed back up with Sorkin in 1995 for the moderately well-received The American President. It didn’t earn the same Oscar buzz, but at least they dumped the whole Bruce Willis-in-a-bunny-suit thing.
19. Kevin Costner, Dances With Wolves > Robin Hood: Prince Of Thieves
Kevin Costner’s bloated-but-affecting Civil War epic Dances With Wolves scored seven Oscars, including Best Director for Costner. (He was also nominated for Best Actor, but lost to Jeremy Irons for Reversal Of Fortune.) Costner’s plainspoken, Midwestern folksiness suited his role as an army lieutenant stranded in the wilds of the Dakota Territory, but it was awkwardly conspicuous in Robin Hood, a quintessentially English tale of the fabled outlaw. Although set in England, Costner sounds like he just flew in from Indianapolis. (Rumor has it he had no choice, as he was unable to pull off a convincing English accent.) It didn’t really matter, as this bland adaptation of the Robin Hood story is unmemorable—though Bryan Adams’ nauseating hit song from the film, “(Everything I Do) I Do It For You” still haunts easy-listening stations everywhere.
20. Peter Sellers, Being There > The Fiendish Plot Of Dr. Fu Manchu
After spending the bulk of the ’70s primarily playing Inspector Clouseau in the Pink Panther series (among other slapsticky roles), Sellers closed the decade by reminding critics of the formidable actor he’d been in the ’50s and ’60s. As a mentally handicapped gardener who inadvertently becomes a political sage in Being There, Sellers was restrained and beatific, creating a character that’s arguably as iconic as Clouseau. (He earned a nomination for Best Actor in the process.) He followed Being There with The Fiendish Plot Of Dr. Fu Manchu, reverting to outlandish (and more than a little racist) character comedy, in the dual roles of a centenarian master criminal and the cop on his tail. Making matters worse, Sellers died of a heart attack after completing Fu Manchu, leaving that movie with the dubious distinction of being his last work as an actor.
21. Sally Field, Norma Rae > Beyond The Poseidon Adventure
Hollywood has always been a precarious place for young actresses, but few starlets have gotten as raw a deal as Sally Field did when she started out in the business. Field launched her career in 1965 with Gidget, a delightful surfer sitcom that showcased her talent splendidly, but didn’t become a hit until it went into summer reruns—after it had been canceled. The team behind Gidget responded to their unexpected success by readying a new sitcom for the fall, and Field signed on, urged by her advisors to maintain her showbiz momentum. That’s how Field ended up spending three years starring in The Flying Nun, a commercially successful but critically derided show that made Field a walking punchline among her peers, right when the culture in Hollywood was favoring the young and the hip. Field spent the ’70s slogging her way back into contention, taking parts in low-budget productions and edgy TV movies like Sybil, before finally breaking through again in 1978 with the labor-union drama Norma Rae. Then the bad-advice bug hit Field again, pushing her to star in the preposterous sequel Beyond The Poseidon Adventure, in which she plays an irritating tugboat passenger beset by terrorists and treasure-hunters, all fighting for the salvage rights of a capsized luxury liner. Field recovered from the indignity of Poseidon and won a second Best Actress Oscar a few years later, for Places In The Heart. It was in that acceptance speech that she delivered the famous line, “You like me,” which has been parodied and mocked for decades since. But the line wasn’t a joke to Field; she had good reason to feel paranoid.
22. Elizabeth Taylor, Butterfield 8 > Cleopatra
Taylor was on a run at the end of the ’50s, landing Best Actress Oscar nominations for 1957’s Raintree County, 1958’s Cat On A Hot Tin Roof, and 1959’s Suddenly Last Summer, before winning the award for playing a neurotic “kept woman” in 1960’s Butterfield 8. The producers of the historical epic Cleopatra asked the newly powerful Taylor to star in their film, figuring that with her critical acclaim and box-office clout, they could raise the money to make the movie they envisioned. Taylor quickly surmised that the producers needed her more than she needed them, and began making demands for script changes, as well as suggesting some of her cronies for positions in the cast and crew. Shooting began in the fall of 1960. Three years, two directors, $44 million, and several Taylor illnesses and diva fits later, Cleopatra was released to critical jeers. The hype surrounding the film—mostly negative, but still intriguing—made Cleopatra one of the top box-office draws of 1963, but Taylor’s reputation took a serious hit. Outside of Who’s Afraid Of Virginia Woolf in 1966, she never made another significant film.
23. Al Pacino, Glengarry Glen Ross > Scent Of A Woman
Late-period Al Pacino is usually about the roar and the bluster; it’s as though, after a long, illustrious career, he’s happily settled down to a steady, nutritious diet of scenery. It worked to terrific effect in Glengarry Glen Ross. As hard-hitting salesman Ricky Roma, Pacino snorts, snarls, and sneers his way through the middle of an equally mesmerizing cast, establishing the high end of the success spectrum for a bunch of mopeish cold-call real-estate salesman. He earned a Supporting Actor Oscar nomination for the role, but lost out to Gene Hackman in Unforgiven—possibly because the Academy was already plotting to give him the Best Actor Oscar for Scent Of A Woman, his follow-up film from the same year. After six previous Best Actor nominations and no wins, the Academy probably felt he was way overdue for the top honors, but it’s just another black mark on the institution’s name that he simultaneously lost for such a terrific role, and won for such a hammy, hackneyed one, “Hoo-ah!” catchphrase and all.