★ = recommended, ♥ = personal favorite

Shakespeare in Love (1998) ★

• starring Gwyneth Paltrow, Joseph Fiennes, Geoffrey Rush, Colin Firth, Ben Affleck, Judi Dench
• directed by John Madden
• 123 minutes, color
• Won 7/13 Oscars, including Best Actress (Paltrow), Best Supporting Actress (Dench) and Best Screenplay

American Beauty (1999) ♥

• starring Kevin Spacey, Annette Bening, Thora Birch, Wes Bentley, Allison Janney, Mena Suvari, Chris Cooper
• directed by Sam Mendes
• 121-122 minutes, color
• Won 5/8 Oscars, including Best Actor (Spacey), Best Director, Best Screenplay and Best Cinematography

Gladiator (2000) ★

• starring Russell Crowe, Joaquin Phoenix, Connie Nielsen, Oliver Reed, Derek Jacobi, Djimon Hounsou, Richard Harris
• directed by Ridley Scott
• 155 minutes, color
• Won 5/12 Oscars, including Best Actor (Crowe)

A Beautiful Mind (2001) ★

• starring Russell Crowe, Ed Harris, Jennifer Connelly, Paul Bettany, Adam Goldberg, Judd Hirsch, Josh Lucas, Anthony Rapp, Christopher Plummer
• directed by Ron Howard
• 135 minutes, color
• Won 4/8 Oscars, including Best Supporting Actress (Connelly), Best Director and Best Screenplay

Chicago (2002) ♥

• starring Renée Zellweger, Catherine Zeta-Jones, Richard Gere, Queen Latifah, John C. Reilly
• directed by Rob Marshall
• 113 minutes, color
• Won 6/13 Oscars, including Best Supporting Actress (Zeta-Jones)

The Lord of the Rings: The Return of the King (2003) ♥

• starring Elijah Wood, Ian McKellen, Viggo Mortensen, Liv Tyler, Sean Astin, Sala Baker, Cate Blanchett, John Rhys-Davies, Bernard Hill, Billy Boyd, Dominic Monaghan, Orlando Bloom, Hugo Weaving, Miranda Otto, David Wenham, Karl Urban, John Noble, Andy Serkis, Ian Holm
• directed by Peter Jackson
• 201-251 minutes, color
• Won 11/11 Oscars, including Best Director and Best Screenplay
  • It has the highest perfect score at the Academy Awards, with 11 wins out of 11 nominations.
  • The only film to win more than 10 Academy Awards without receiving a single acting nomination.
  • At 35 letters, this film has the longest title of any Best Picture winner. It also set the record for the number of words in a Best Picture title, with 10.

Million Dollar Baby (2004) ★

• starring Clint Eastwood, Hilary Swank, Morgan Freeman
• directed by Clint Eastwood
• 132 minutes, color
• Won 4/7 Oscars, including Best Actress (Swank), Best Supporting Actor (Freeman) and Best Director

Crash (2004)

• starring Sandra Bullock, Don Cheadle, Matt Dillon, Jennifer Esposito, Michael Peña, Brendan Fraser, Terrence Howard, Ludacris, Thandie Newton, Ryan Phillippe, Larenz Tate
• directed by Paul Haggis
• 112 minutes, color
• Won 3/6 Oscars, including Best Screenplay
  • The first film to be set primarily or entirely in Los Angeles and win Best Picture.

The Departed (2006) ♥

• starring Leonardo DiCaprio, Matt Damon, Jack Nicholson, Mark Wahlberg, Martin Sheen, Ray Winstone, Vera Farmiga, Anthony Anderson, Alec Baldwin
• directed by Martin Scorsese
• 151 minutes, color
• Won 4/5 Oscars, including Best Director and Best Screenplay
  • The only remake of a foreign film to win Best Picture.
  • This film has the most uses of the word "fuck" and its derivatives (237) to win the Best Picture Oscar.

No Country for Old Men (2007) ♥

• starring Tommy Lee Jones, Javier Bardem, Josh Brolin, Woody Harrelson, Kelly Macdonald, Garret Dillahunt, Tess Harper
• directed by Joel Coen, Ethan Coen
• 122 minutes, color
• Won 4/8 Oscars, including Best Supporting Actor (Bardem), Best Director and Best Screenplay
  • The second film to win a Best Director Oscar for two directors.
  • The second Best Picture winner to be produced, directed, written, and edited by the same person (two in this case: Joel Coen and Ethan Coen).
  • Javier Bardem became the first Spanish actor to win an Oscar.