Most Surprising Oscar Winners of the Past 20 Years

by englehar | created - 09 Sep 2010 | updated - 21 Sep 2010 | Public

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.

 Refine See titles to watch instantly, titles you haven't rated, etc
  • Instant Watch Options
  • Genres
  • Movies or TV
  • IMDb Rating
  • In Theaters
  • Release Year
  • Keywords



IMDb user rating (average) to
Number of votes to »



Reset
Release year or range to »




































































































1. Crash (I) (2004)

14A | 112 min | Crime, Drama, Thriller

66 Metascore

Los Angeles citizens with vastly separate lives collide in interweaving stories of race, loss and redemption.

Director: Paul Haggis | Stars: Don Cheadle, Sandra Bullock, Thandiwe Newton, Karina Arroyave

Votes: 421,687 | Gross: $54.58M

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.

2. The Pianist (2002)

AA | 150 min | Biography, Drama, Music

85 Metascore

A Polish Jewish musician struggles to survive the destruction of the Warsaw ghetto of World War II.

Director: Roman Polanski | Stars: Adrien Brody, Thomas Kretschmann, Frank Finlay, Emilia Fox

Votes: 740,923 | Gross: $32.57M

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.

3. The Piano (1993)

18A | 121 min | Drama, Music, Romance

89 Metascore

In 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 wealthy landowner, but is soon lusted after by a local worker on the plantation.

Director: Jane Campion | Stars: Holly Hunter, Harvey Keitel, Sam Neill, Anna Paquin

Votes: 79,723 | Gross: $40.16M

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.

4. Shakespeare in Love (1998)

14A | 123 min | Comedy, Drama, History

87 Metascore

The 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.

Director: John Madden | Stars: Gwyneth Paltrow, Joseph Fiennes, Geoffrey Rush, Tom Wilkinson

Votes: 215,375 | Gross: $100.32M

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.

5. My Cousin Vinny (1992)

14A | 120 min | Comedy, Crime

68 Metascore

Two 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.

Director: Jonathan Lynn | Stars: Joe Pesci, Marisa Tomei, Ralph Macchio, Mitchell Whitfield

Votes: 108,719 | Gross: $52.93M

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.

6. The English Patient (1996)

14A | 162 min | Drama, Romance, War

87 Metascore

At 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.

Director: Anthony Minghella | Stars: Ralph Fiennes, Juliette Binoche, Willem Dafoe, Kristin Scott Thomas

Votes: 180,245 | Gross: $78.65M

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.

7. The Pianist (2002)

AA | 150 min | Biography, Drama, Music

85 Metascore

A Polish Jewish musician struggles to survive the destruction of the Warsaw ghetto of World War II.

Director: Roman Polanski | Stars: Adrien Brody, Thomas Kretschmann, Frank Finlay, Emilia Fox

Votes: 740,923 | Gross: $32.57M

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).

8. La vita è bella (1997)

PG | 116 min | Comedy, Drama, Romance

59 Metascore

When an open-minded Jewish librarian 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.

Director: Roberto Benigni | Stars: Roberto Benigni, Nicoletta Braschi, Giorgio Cantarini, Giustino Durano

Votes: 631,600 | Gross: $57.60M

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.

9. Boys Don't Cry (1999)

R | 118 min | Biography, Crime, Drama

86 Metascore

A young man named Brandon Teena navigates love, life, and being transgender in rural Nebraska.

Director: Kimberly Peirce | Stars: Hilary Swank, Chloë Sevigny, Peter Sarsgaard, Brendan Sexton III

Votes: 92,961 | Gross: $11.53M

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.

10. Traffic (2000)

14A | 147 min | Crime, Drama, Thriller

86 Metascore

A 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.

Director: Steven Soderbergh | Stars: Michael Douglas, Benicio Del Toro, Catherine Zeta-Jones, Jacob Vargas

Votes: 197,119 | Gross: $124.12M

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.

11. Pollock (2000)

18+ | 122 min | Biography, Drama

77 Metascore

A film about the life and career of the American painter, Jackson Pollock.

Director: Ed Harris | Stars: Ed Harris, Marcia Gay Harden, Robert Knott, Molly Regan

Votes: 27,048 | Gross: $8.60M

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).

12. 8 Mile (2002)

18A | 110 min | Drama, Music

77 Metascore

A young rapper, struggling with every aspect of his life, wants to make it big but his friends and foes make this odyssey of rap harder than it may seem.

Director: Curtis Hanson | Stars: Eminem, Brittany Murphy, Kim Basinger, Mekhi Phifer

Votes: 252,099 | Gross: $116.72M

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.

13. Bowling for Columbine (2002)

18 | 120 min | Documentary, Crime, Drama

72 Metascore

Filmmaker Michael Moore explores the roots of America's predilection for gun violence.

Director: Michael Moore | Stars: Michael Moore, Charlton Heston, Marilyn Manson, Salvador Allende

Votes: 140,124 | Gross: $21.58M

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.

14. Hustle & Flow (2005)

14A | 116 min | Crime, Drama, Music

68 Metascore

With help from his friends, a Memphis pimp in a mid-life crisis attempts to become a successful hip-hop emcee.

Director: Craig Brewer | Stars: Terrence Howard, Ludacris, Anthony Anderson, Taryn Manning

Votes: 38,796 | Gross: $22.20M

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.

15. The Blind Side (2009)

PG | 129 min | Biography, Drama, Sport

53 Metascore

The 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.

Director: John Lee Hancock | Stars: Quinton Aaron, Sandra Bullock, Tim McGraw, Jae Head

Votes: 296,447 | Gross: $255.96M

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.

16. Iris (I) (2001)

AA | 91 min | Biography, Drama, Romance

76 Metascore

True 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.

Director: Richard Eyre | Stars: Judi Dench, Jim Broadbent, Kate Winslet, Hugh Bonneville

Votes: 17,295 | Gross: $1.29M

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.

17. Monster's Ball (2001)

18A | 111 min | Drama, Romance

69 Metascore

After 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.

Director: Marc Forster | Stars: Billy Bob Thornton, Halle Berry, Taylor Simpson, Gabrielle Witcher

Votes: 83,187 | Gross: $31.25M

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.

18. La Vie En Rose (2007)

PG-13 | 140 min | Biography, Drama, Music

66 Metascore

Biopic 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.

Director: Olivier Dahan | Stars: Marion Cotillard, Sylvie Testud, Pascal Greggory, Emmanuelle Seigner

Votes: 83,295 | Gross: $10.30M

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.

19. The Lives of Others (2006)

14A | 137 min | Drama, Mystery, Thriller

89 Metascore

In 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.

Director: Florian Henckel von Donnersmarck | Stars: Ulrich Mühe, Martina Gedeck, Sebastian Koch, Ulrich Tukur

Votes: 362,823 | Gross: $11.29M

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.

20. Sen to Chihiro no kamikakushi (2001)

PG | 125 min | Animation, Adventure, Family

96 Metascore

During 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.

Director: Hayao Miyazaki | Stars: Daveigh Chase, Suzanne Pleshette, Miyu Irino, Rumi Hiiragi

Votes: 662,942 | Gross: $10.06M

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.



Recently Viewed