Most Surprising Oscar Winners of the Past 20 Years
What movies, actors and directors provided the biggest shocks and surprises of the past 20 years at the Academy Awards? Read below to find our list of those whose wins still remain memorable and groundbreaking.
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- DirectorPaul HaggisStarsDon CheadleSandra BullockThandiwe NewtonLos Angeles citizens with vastly separate lives collide in interweaving stories of race, loss and redemption.The surprise Best Picture winner bested favorite Brokeback Mountain thanks to an aggressive campaign, and caused behind-the-scenes drama regarding the number of producers eligible for a nomination/win.
- DirectorRoman PolanskiStarsAdrien BrodyThomas KretschmannFrank FinlayDuring WWII, acclaimed Polish musician Wladyslaw faces various struggles as he loses contact with his family. As the situation worsens, he hides in the ruins of Warsaw in order to survive.Up against Jack Nicholson, Daniel Day-Lewis, Nicolas Cage and Michael Caine, Brody shocked the audience with his Best Actor win -- and presenter Halle Berry as well, upon whom he planted a big, huge kiss.
- DirectorJane CampionStarsHolly HunterHarvey KeitelSam NeillIn the mid-19th century a mute woman is sent to New Zealand along with her young daughter and prized piano for an arranged marriage to a farmer, but is soon lusted after by a farm worker.11 year-old Anna Paquin became the second youngest person to win an Oscar when she nabbed the Best Supporting Actress Oscar away from Rosie Perez, Emma Thompson, Winona Ryder and Piano co-star Holly Hunter, who was nominated for The Firm.
- DirectorJohn MaddenStarsGwyneth PaltrowJoseph FiennesGeoffrey RushThe world's greatest-ever playwright, William Shakespeare, is young, out of ideas, and short of cash, but meets his ideal woman and is inspired to write one of his most famous plays.So confident was everyone that Steven Spielberg's Saving Private Ryan would take home the Best Picture award that Indiana Jones himself, Harrison Ford, was the Best Picture presenter. But Harvey Weinstein sailed to victory with the little British comedy that could.
- DirectorJonathan LynnStarsJoe PesciMarisa TomeiRalph MacchioTwo New Yorkers accused of murder in rural Alabama while on their way back to college call in the help of one of their cousins, a loudmouth lawyer with no trial experience.Marisa Tomei's surprise Best Supporting Actress win created a maelstrom of controversy that presenter Jack Palance had misread the actual recipient; two Oscar nominations later, everyone knows that is most definitely not the case.
- DirectorAnthony MinghellaStarsRalph FiennesJuliette BinocheWillem DafoeAt the close of World War II, a young nurse tends to a badly burned plane crash victim. His past is shown in flashbacks, revealing an involvement in a fateful love affair.Lauren Bacall was expected to be the sentimental favorite for Best Supporting Actress (for The Mirror Has Two Faces) but the lovely Binoche was the shocked winner, stating that it was Bacall who indeed deserved the statuette.
- DirectorRoman PolanskiStarsAdrien BrodyThomas KretschmannFrank FinlayDuring WWII, acclaimed Polish musician Wladyslaw faces various struggles as he loses contact with his family. As the situation worsens, he hides in the ruins of Warsaw in order to survive.On top of star Adrien Brody's surprise win, the absent Polanski was the recipient of the Best Director Oscar over Chicago's Rob Marshall (who had won the DGA prize that year).
- DirectorRoberto BenigniStarsRoberto BenigniNicoletta BraschiGiorgio CantariniWhen an open-minded Jewish waiter and his son become victims of the Holocaust, he uses a perfect mixture of will, humor and imagination to protect his son from the dangers around their camp.Roberto Begnini danced on top of the seats as he made his way to the podium to accept Best Actor honors over Nick Nolte, Edward Norton, Tom Hanks and Ian McKellen.
- DirectorKimberly PeirceStarsHilary SwankChloë SevignyPeter SarsgaardA young transgender man named Brandon navigates love, life, and trying to pass as a boy in rural Nebraska.Hilary Swank was a little known actress whose primary credits were The Next Karate Kid and Beverly Hills 90210 when she swept the Best Actress award with her sensitive portrayal of transgendered teen Brandon Teena.
- DirectorSteven SoderberghStarsMichael DouglasBenicio Del ToroCatherine Zeta-JonesA conservative judge is appointed by the President to spearhead America's escalating war against drugs, only to discover that his teenage daughter is a crack addict. Two DEA agents protect an informant. A jailed drug baron's wife attempts to carry on the family business.Competing against himself for Erin Brockovich, Soderbergh was expected to split his own vote for Best Director, to be bested by either Ang Lee of Crouching Tiger, Hidden Dragon or Ridley Scott of Gladiator; instead, he took home the award for the acclaimed drama.
- DirectorEd HarrisStarsEd HarrisMarcia Gay HardenRobert KnottA film about the life and career of the American painter, Jackson Pollock.In a Best Supporting Actress field that could have gone any way, Marcia Gay Harden bested performances by Kate Hudson and Frances McDormand (Almost Famous), Julie Walters (Billy Elliott), and Judi Dench (Chocolat).
- DirectorCurtis HansonStarsEminemBrittany MurphyKim BasingerFollows a young rapper in the Detroit area, struggling with every aspect of his life; he wants to make it big but his friends and foes make this odyssey of rap harder than it may seem.A surprised Barbra Streisand presented the Best Song Oscar to "Lose Yourself," the first rap song when Eminem's hit won the award; the star and rapper himself, however, was not present to collect his honor.
- DirectorMichael MooreStarsMichael MooreCharlton HestonMarilyn MansonFilmmaker Michael Moore explores the roots of America's predilection for gun violence.Though it was a huge hit, few expected Michael Moore to take home the Oscar for Best Documentary feature for the controversial hit; when he won, Moore was almost booed off the stage thanks to his passionate acceptance speech.
- DirectorCraig BrewerStarsTerrence HowardLudacrisAnthony AndersonWith help from his friends, a Memphis pimp in a mid-life crisis attempts to become a successful hip-hop emcee.Up against Dolly Parton's country song for Transamerica and a haunting ballad from Crash, the rousing "It's Hard Out Here for a Pimp" brought the house down in live performance before snapping up the Best Song Oscar.
- DirectorJohn Lee HancockStarsQuinton AaronSandra BullockTim McGrawThe story of Michael Oher, a homeless and traumatized boy who became an All-American football player and first-round NFL draft pick with the help of a caring woman and her family.Sandra Bullock made a huge comeback with this inspirational drama, and the wave of popularity rode her to a Best Actress Oscar over the likes of Meryl Streep, who also won hearts as Julia Child in Julie & Julia.
- DirectorRichard EyreStarsJudi DenchJim BroadbentKate WinsletTrue story of the lifelong romance between novelist Iris Murdoch and her husband John Bayley, from their student days through her battle with Alzheimer's disease.Having appeared also in Moulin Rouge and Bridget Jones's Diary that year, Jim Broadbent took home the Best Supporting Actor Oscar for this sensitive drama about author Iris Murdoch and her devoted husband.
- DirectorMarc ForsterStarsBilly Bob ThorntonHalle BerryTaylor SimpsonAfter a family tragedy, a racist prison guard re-examines his attitudes while falling in love with the African-American wife of the last prisoner he executed.Though she had won the Screen Actors Guild award earlier, the shock on Halle Berry's face when she won Best Actress (and became the first African-American woman to do so) brought down the house and earned her a standing ovation.
- DirectorOlivier DahanStarsMarion CotillardSylvie TestudPascal GreggoryBiopic of the iconic French singer Édith Piaf. Raised by her grandmother in a brothel, she was discovered while singing on a street corner at the age of 19. Despite her success, Piaf's life was filled with tragedy.Though it was a big hit in France, few had seen this biopic of singer Edith Piaf stateside, until a highly successful campaign brought the heretofore unknown Marion Cotillard to mainstream popularity and an Oscar for Best Actress.
- DirectorFlorian Henckel von DonnersmarckStarsUlrich MüheMartina GedeckSebastian KochIn 1984 East Berlin, an agent of the secret police conducting surveillance on a writer and his lover finds himself becoming increasingly absorbed by their lives.When Pan's Labryinth nabbed three Oscars (Cinematography, Art Direction, Make-up), it was widely assumed it would win Best Foreign Language Film as well; enter the acclaimed German drama to sweep the award instead.
- DirectorHayao MiyazakiStarsDaveigh ChaseSuzanne PleshetteMiyu IrinoDuring her family's move to the suburbs, a sullen 10-year-old girl wanders into a world ruled by gods, witches and spirits, and where humans are changed into beasts.In a new category that was dominated by huge box office hits, Hayao Miyazaki's haunting film bested hits like Lilo & Stitch and Ice Age for the Best Animated Feature Oscar.
