Oscar Winners Best male Supporting Actor

In their movies they played the side part, but at the Oscars they were the main attraction.
Our list of the Academy Award Winners for Best male Supporting Actor!

1999 – Michael Caine (The Cider House Rules)

The Cider House Rules is a 1999 American drama film directed by Lasse Hallström, based on John Irving’s novel of the same name. The film had its world premiere at the 56th Venice Film Festival. The film tells of the coming-of-age of Homer Wells, who lives in a World War II-era Maine orphanage run by Dr. Wilbur Larch (Michael Caine) who performs illegal abortions.

2000 – Benicio del Toro (Traffic)

Traffic is a 2000 American crime drama film directed by Steven Soderbergh and written by Stephen Gaghan. It explores the illegal drug trade from a number of perspectives: users, enforcers, politicians, and traffickers. Their stories are edited together throughout the film, although some of the characters do not meet each other. Benicio del Toro plays Javier Rodriguez, a Mexican police officer.

2001 – Jim Broadbent (Iris)

Iris is a 2001 British-American biographical drama film that tells the story of Irish-born British novelist Dame Iris Murdoch and her relationship with John Bayley. The film contrasts the start of their relationship, when Murdoch (Kate Winslet) was an outgoing, dominant individual as compared to her timid and scholarly partner Bayley (Hugh Bonneville), and their later life, when Murdoch (Judi Dench) was suffering from Alzheimer’s disease and tended to by a frustrated Bayley (Jim Broadbent) in their North Oxford home in Charlbury Road.

2002 – Chris Cooper (Adaption)

Adaptation stars Nicolas Cage as Kaufman and his fictional twin brother Donald, Meryl Streep as Orlean, and Chris Cooper as John Laroche, with Cara Seymour, Brian Cox, Tilda Swinton, Ron Livingston, and Maggie Gyllenhaal in supporting roles. Adaptation also adds a number of fictitious elements, including Kaufman’s twin brother and a romance between Orlean and Laroche, and culminates in completely invented events including fictional versions of Orlean and Laroche three years after the events related in The Orchid Thief.

2003 – Tim Robbins (Mystic River)

Mystic River is a 2003 American mystery film directed and scored by Clint Eastwood. It stars Sean Penn, Tim Robbins, Kevin Bacon, Laurence Fishburne, Marcia Gay Harden, and Laura Linney. It was nominated for Academy Awards for Best Picture, Best Director, Best Actor, Best Adapted Screenplay, Best Supporting Actress, and Best Supporting Actor. Penn won Best Actor and Robbins won Best Supporting Actor, making Mystic River the first film to win both awards since Ben-Hur in 1959.

2004 – Morgan Freeman (Million Dollar Baby)

Million Dollar Baby is about an underappreciated boxing trainer, the mistakes that haunt him from his past, and his quest for atonement by helping an underdog amateur boxer achieve her dream of becoming a professional. Morgan Freeman plays Eddie “Scrap-Iron” Dupris, a gym assistant; an elderly former boxer,who was blinded in one eye in his last fight.

2005 – George Clooney (Syriana)

Syriana is loosely adapted from ex CIA operative Robert Baer’s memoir See No Evil. The film focuses on petroleum politics and the global influence of the oil industry, whose political, economic, legal, and social effects are experienced by a Central Intelligence Agency operative (George Clooney), an energy analyst (Matt Damon), a Washington, D.C. attorney (Jeffrey Wright), and a young unemployed Pakistani migrant worker (Mazhar Munir) in an Arab state in the Persian Gulf. 

2006 – Alan Arkin (Little Miss Sunshine)

Little Miss Sunshine is a 2006 American comedy-drama road film and the directorial debut of the husband-wife team of Jonathan Dayton and Valerie Faris. The screenplay was written by first-time writer Michael Arndt. The film stars Greg Kinnear, Steve Carell, Toni Collette, Paul Dano, Abigail Breslin, and Alan Arkin, and was produced by Big Beach Films on a budget of US$8 million. Filming began on June 6, 2005 and took place over 30 days in Arizona and Southern California.

2007 – Javier Bardem (No Country for Old Men)

No Country for Old Men is a 2007 American neo-Western crime thriller film written and directed by Joel and Ethan Coen, based on Cormac McCarthy’s 2005 novel of the same name. A cat and mouse thriller starring Tommy Lee Jones, Javier Bardem, and Josh Brolin, it follows a Texas welder and Vietnam War veteran in the desert landscape of 1980 West Texas. Javier Bardem plays the hitman Anton Chigurh.

2008 – Heath Ledger (The Dark Knight)

The Dark Knight, based on the DC Comics character Batman. In the film, Bruce Wayne / Batman (Christian Bale), Police Lieutenant James Gordon (Gary Oldman) and District Attorney Harvey Dent (Aaron Eckhart) form an alliance to dismantle organized crime in Gotham City, but are menaced by an anarchistic mastermind known as the Joker(Heath Ledger), who seeks to undermine Batman’s influence and turn the city to chaos.