The Oscars are meant to be the greatest honor in entertainment. Winning an Oscar can change a person’s career overnight, as receiving such an honor in front of all the most important people in Hollywood can open a lot of doors. The 2000s were, overall, a great time for the Academy. Generation-defining movies likeThe Lord of the Rings: The Return of the Kingbroke records, while indie efforts likeSidewaysandLittle Miss Sunshinemade a huge splash.
However, it wasn’t all great. Indeed, for every great and timeless win at the Oscars throughout the noughties, there’s also a truly questionable and often eye-rolling win rearing its ugly head.This list will rank the worst Oscar wins of the 2000sbased on how controversial they were at the time and how poorly they have aged since. Expect to see all the usual suspects here, but also prepare to see some surprising choices that might cause some divided opinions.
10Hilary Swank
Best Actress 2005 for ‘Million Dollar Baby’ (2004)
Hilary Swankgives a very good performance inMillion Dollar Baby. It’s a very demanding role, physically and emotionally, and she knocks it out of the park. Even as the movie descends into manipulative melodrama in the third act, Swank keeps her character grounded, making the emotions real and keeping the ending from crumbling on itself.
Yes, Swank was worthy of her Oscar. As always, the question we must ask ourselves is,“Was sheworthierthan her fellow nominees?“Those included a larger-than-lifeAnnette Beningsingle-handedly savingBeing Juliafrom mediocrity,Kate WinsletandImelda Stauntongiving career-best and career-defining performances inEternal Sunshine of the Spotless MindandVera Drake, andCatalina Sandino Morenogiving one of the greatest acting debuts of the 21st century inMaria Full of Grace. Considering the sheer talent in this category, and the fact that Swank had already won an Oscar barely five years before,the answer is probably “no.”
Million Dollar Baby
9’Memoirs of a Geisha' (2005)
Best Cinematography 2006
Memoirs of a Geishais such a bizarre movie. Surrounded in controversy from the get-go, the film opened in 2005 to a divided critical reception, with the casting of several Chinese women in leading roles andRob Marshall’s style-over-substance approach receiving the most heat. Ultimately,Memoirs of a Geishawon three Oscars, two of which — Art Direction and Costume Design — are uncontested.
However, its victory in Best Cinematography continues to raise some eyebrows, mainly because of the other nominees in the category, some of which can arguably be considered worthier.Rodrigo Prieto’s breathtaking work onBrokeback Mountainand especiallyEmmanuel Lubezki’s utterly magnificent work onThe New Worldwould’ve been far better choices in the category.Memoirs of a Geisha’s cinematography is good, butnothing to write home about.
Memoirs Of A Geisha
8Renée Zellweger
Best Supporting Actress 2004 for ‘Cold Mountain’ (2003)
Few actresses did better throughout the early 2000s thanRenée Zellweger. Following her breakthrough in the mid-90s, Zellweger became one of the most bankable stars of the noughties, earning three consecutive Oscar nominations for her work inBridget Jones’s Diary,Chicago, andCold Mountain, ultimately winning for the latter.
Had Zellweger’s first victory come forChicagoor evenBridget Jones, then it wouldn’t be so infamous. However,Cold Mountainis one of those fancy, elaborate period pieces thatshamelessly scream “Oscar bait.“The film’s association with disgraced and convicted felonHarvey Weinsteinfurther stains its legacy. In the acting department, Zellweger is fine, but her performance hardly warranted a nomination, let alone a win. In a fair world,Shohreh Aghdashloo’s powerful work inHouse of Sand and Fogwould’ve emerged victorious.
Cold Mountain
7Kate Winslet
Best Actress 2009 for ‘The Reader’ (2008)
By 2008,Kate Winslet already had five Oscar nominations. Moreover, she had delivered more than a few worthy performances, with many believing she should’ve won for her first nomination,Sense and Sensibility. Indeed, by this point, Winslet was considered “overdue.” EnterThe Reader, an utterly conventional World War II drama that sees Winslet as a former concentration camp guard standing trial.
The Readeris not a great movie; it’s simple and has aged like milk, but if there’s one highlight in it, it’s Kate Winslet. Still, for all her efforts, the performance is quite showy;you can tell she had Oscar in her mind in pretty much every scene, and that’s never good. Her efforts paid off, and she walked away with the golden statuette for what is probably the worst of her seven nominations so far.Meryl Streep’s work inDoubtshould’ve probably prevailed here, especially because the real winner,Sally Hawkinsfor her irresistible performance inHappy-Go-Lucky, wasn’t even nominated.
The Reader
6Sean Penn
Best Actor 2004 for ‘Mystic River’ (2003)
In hindsight,Mystic River’s success at the Oscars is truly puzzling. The film is a solid crime drama fromClint Eastwoodfeaturing fine performances from its talented cast.Sean Pennis pretty good in one of the lead roles, but, especially twenty-something years later, it’s hard not to see his Best Actor win ascompensation for his previous lossesinDead Man WalkingandSweet and Lowdown.
Penn has one splashy scene inMystic River, where his character finds out his daughter’s death and loudly mourns her. Other than that, the film is mostly a showcase forTim Robbins, who won the Supporting Actor Oscar, andKevin Bacon, who was unfairly overlooked throughout the season. Of the nominees,Bill Murray’s against-type performance inSofia Coppola’sLost in Translationprobably deserved to win, especially considering Penn would win a second Oscar only four years later for a much worthier performance.
Mystic River
5Sir Michael Caine
Best Supporting Actor 2000 for ‘The Cider House Rules’ (1999)
SirMichael Cainewon a richly deserved Best Supporting Actor Oscar in 1987 forHannah and Her Sistersand would’ve made for a very worthy Best Actor winner for eitherAlfieorEducating Rita. With such a prolific and legendary career, it’s something of a shame, then, that Caine’s second Oscar came for such a forgettable movie asThe Cider House Rules.
Caine is perfectly fine in the movie, butperfectly fine performances shouldn’t win Oscars. The competition in his category was an embarrassment of riches, too:Tom Cruisewith the performance of his career inMagnolia, the lateMichael Clarke Duncanbreaking everyone’s hearts inThe Green Mile, andHaley Joel Osmentdelivering a masterclass in dread inThe Sixth Sense. Any of them would’ve been far better winners, especially Cruise, andit’s a shame the Academy went for the most boring choice.
The Cider House Rules
4’The Cider House Rules' (1999)
Best Adapted Screenplay 2000
And speaking ofThe Cider House Rules, the film won another major award at the 2000 ceremony: Best Adapted Screenplay. In any other year, it would’ve been a decent winner; indeed,John Irvingdoes a pretty good job adapting his 1985 novel. However, looking back at the category, it’s truly wild that the Academy chose what isquite possibly the worst of the five nominees.
Michael MannandEric Rothdid terrific work adaptingThe Insider,Frank Darabontcemented his place as the ultimateStephen King-adapted with his work onThe Green Mile, andAnthony Minghellabreathed sexy new life intoThe Talented Mr. Ripley. More interesting would’ve been a win forAlexander PayneandJim Taylor, who adaptedElectioninto one of the most biting andinsightful political satires of the 20th centurydisguised as a teen drama.
3’A Beautiful Mind' (2001)
Best Picture 2002
Ron Howard’sA Beautiful Mindis probably the most biopic-y biopic movie of the 21st century, which is saying something. The film tells the story of mathematicianJohn Nash(Russell Crowe), whose work with the military regarding top-secret code-breaking duties led him to develop a mental illness.
Everything aboutA Beautiful Mindis painfully conventional, from the title to the by-the-numbers approach to what should be a deeply moving story. The one saving grace isRussell Crowe in one of his best performances, and he’s almost good enough to elevate the movie past its banality. In hindsight, its Best Picture win seems wholly undeserving, especially considering it was against what is now considered one of the greatest fantasy epics of all time:The Lord of the Rings: The Fellowship of the Ring.
A Beautiful Mind
2’American Beauty' (1999)
Best Picture, Best Director, Best Actor, Best Original Screenplay 2000
Few movies haveaged as badly asAmerican Beauty. TheSam Mendes-directed drama follows the disintegration of a well-off family living in a wealthy suburb. It features well-known themes that have been explored better in other works, but in 1999, it seemed groundbreaking and exciting. Well… not anymore!
Now,American Beautyis not a bad film; it’s competently made and performed, Annette Bening is genuinely great as the slowly-unraveling Caroline, and the score is pretty good. However, it’s hard to see it as anything more than a solid, albeit profoundly superficial, dissection of the hidden nightmare of suburbia. It’s all surface here;American Beautydoes nothing but acknowledge issues that it’s not clever enough to dissect. In terms of sheer originality and impact,The Sixth Senseshould’ve probably won Best Picture in a landslide. Well, at least it wasn’tThe Cider House Rules.
American Beauty
1’Crash' (2004)
Best Picture, Best Original Screenplay, Best Editing 2006
No movie of the 21st century is more derided by Oscar fans thanCrash, not evenGreen Book. The 2004 drama byPaul Haggisfeatures a large ensemble of actors in service of a sprawling story set in modern-day Los Angeles about race relations and issues facing several minorities.
Crash’s wins at the 2006 Academy Awards are the stuff of Hollywood infamy. Who can forget when a genuinely shockedJack NicholsonpresentedCrashwith the Best Picture Oscar with an expression that very much amounts to, “Are you seeing this?” The thing is, the film’s dubious reputation is wholly deserved:Crashis clumsy in its treatment of racial issues, laughably oversimplifying them to the point whereits narrative comes across as preachy and ineptrather than deep and impactful. The screenplay is also absurdly basic, lacking any nuance or insight into its dynamics. Twenty years later,Crash’s Best Picture winner is more derided than ever, but hey,at leastRoger Ebertliked it.
