| Year
|
Winners and nominees
|
Film
|
Role
|
| 1996 |
Tom Cruise |
Jerry Maguire |
Jerry Maguire ‡
|
| Nathan Lane |
The Birdcage |
Albert Goldman
|
| Eddie Murphy |
The Nutty Professor |
Sherman Klump / Various Characters
|
| Jack Nicholson |
Mars Attacks! |
James Dale
|
| Stanley Tucci |
Big Night |
Secondo
|
| 1997 |
Jack Nicholson |
As Good as It Gets |
Melvin Udall †
|
| Robert Carlyle |
The Full Monty |
Gary "Gaz" Schofield
|
| Dustin Hoffman |
Wag the Dog |
Stanley Motss ‡
|
| Tommy Lee Jones |
Men in Black |
Kevin Brown / Agent K
|
| Kevin Kline |
In & Out |
Howard Brackett
|
| Howard Stern |
Private Parts |
Himself
|
| 1998 |
Ian Bannen |
Waking Ned |
Jackie O'Shea
|
| David Kelly |
Waking Ned |
Michael O'Sullivan
|
| Warren Beatty |
Bulworth |
Senator Jay Billington Bulworth
|
| Jeff Bridges |
The Big Lebowski |
Jeffrey "The Dude" Lebowski
|
| Michael Caine |
Little Voice |
Ray Say
|
| Robin Williams |
Patch Adams |
Hunter "Patch" Adams
|
| 1999 |
Philip Seymour Hoffman |
Flawless |
Rusty
|
| Jim Carrey |
Man on the Moon |
Andy Kaufman
|
| Johnny Depp |
Sleepy Hollow |
Ichabod Crane
|
| Rupert Everett |
An Ideal Husband |
Arthur Goring
|
| Sean Penn |
Sweet and Lowdown |
Emmet Ray ‡
|
| Steve Zahn |
Happy, Texas |
Wayne Wayne Wayne, Jr. (a.k.a. David)
|
| 2000 |
Michael Douglas |
Wonder Boys |
Grady Tripp
|
| George Clooney |
O Brother, Where Art Thou? |
Ulysses Everett McGill
|
| Richard Gere |
Dr. T & the Women |
Dr. Sullivan Travis (Dr. T)
|
| Christopher Guest |
Best in Show |
Harlan Pepper
|
| Eddie Murphy |
Nutty Professor II: The Klumps |
Sherman Klump / Various Characters
|
| Edward Norton |
Keeping the Faith |
Brian Finn
|
| 2001 |
Ewan McGregor |
Moulin Rouge! |
Christian
|
| Colin Firth |
Bridget Jones's Diary |
Mark Darcy
|
| Gene Hackman |
The Royal Tenenbaums |
Royal Tenenbaum
|
| John Cameron Mitchell |
Hedwig and the Angry Inch |
Hansel Schmidt / Hedwig Robinson
|
| Ben Stiller |
Zoolander |
Derek Zoolander
|
| Chris Tucker |
Rush Hour 2 |
James Carter
|
| 2002 |
Kieran Culkin |
Igby Goes Down |
Jason "Igby" Slocumb, Jr.
|
| Nicolas Cage |
Adaptation. |
Charlie and Donald Kaufman ‡
|
| Hugh Grant |
About a Boy |
Will Freeman
|
| Sam Rockwell |
Confessions of a Dangerous Mind |
Chuck Barris
|
| Adam Sandler |
Punch-Drunk Love |
Barry Egan
|
| Aaron Stanford |
Tadpole |
Oscar Grubman
|
| 2003 |
Bill Murray |
Lost in Translation |
Bob Harris ‡
|
| Jack Black |
School of Rock |
Dewey Finn
|
| Johnny Depp |
Pirates of the Caribbean: The Curse of the Black Pearl |
Capt. Jack Sparrow ‡
|
| Robert Downey Jr. |
The Singing Detective |
Dan Dark
|
| Paul Giamatti |
American Splendor |
Harvey Pekar
|
| Billy Bob Thornton |
Bad Santa |
Willie T. Stokes
|
| 2004 |
Jamie Foxx |
Ray |
Ray Charles †
|
| Gerard Butler |
The Phantom of the Opera |
The Phantom
|
| Jim Carrey |
Eternal Sunshine of the Spotless Mind |
Joel Barish
|
| Paul Giamatti |
Sideways |
Miles Raymond
|
| Kevin Kline |
De-Lovely |
Cole Porter
|
| Bill Murray |
The Life Aquatic with Steve Zissou |
Steve Zissou
|
| 2005 |
Terrence Howard |
Hustle & Flow |
DJay ‡
|
| Kevin Costner |
The Upside of Anger |
Denny Davies
|
| Robert Downey Jr. |
Kiss Kiss Bang Bang |
Harry Lockhart
|
| Cillian Murphy |
Breakfast on Pluto |
Patrick "Kitten" Braden
|
| Bill Murray |
Broken Flowers |
Don Johnston
|
| Joaquin Phoenix |
Walk the Line |
Johnny Cash ‡
|
| 2006 |
Joseph Cross |
Running with Scissors |
Augusten Burroughs
|
| Sacha Baron Cohen |
Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan |
Borat Sagdiyev
|
| Aaron Eckhart |
Thank You for Smoking |
Nick Naylor
|
| Will Ferrell |
Stranger than Fiction |
Harold Crick
|
| Peter O'Toole |
Venus |
Maurice Russell ‡
|
| 2007 |
Ryan Gosling |
Lars and the Real Girl |
Lars Lindstrom
|
| Don Cheadle |
Talk to Me |
Ralph Greene, Jr.
|
| Richard Gere |
The Hoax |
Clifford Irving
|
| Ben Kingsley |
You Kill Me |
Frank Falenczyk
|
| Clive Owen |
Shoot 'Em Up |
Mr. Smith
|
| Seth Rogen |
Knocked Up |
Ben Stone
|
| 2008 |
Ricky Gervais |
Ghost Town |
Bertram Pincus
|
| Josh Brolin |
W. |
George W. Bush
|
| Michael Cera |
Nick and Norah's Infinite Playlist |
Nick O'Leary
|
| Brendan Gleeson |
In Bruges |
Ken Daley
|
| Sam Rockwell |
Choke |
Victor Mancini
|
| Mark Ruffalo |
The Brothers Bloom |
Stephen
|
| 2009 |
Michael Stuhlbarg |
A Serious Man |
Larry Gopnik
|
| George Clooney |
Up in the Air |
Ryan Bingham ‡
|
| Bradley Cooper |
The Hangover |
Phil Wenneck
|
| Matt Damon |
The Informant! |
Mark Whitacre
|
| Daniel Day-Lewis |
Nine |
Guido Contini
|
| 2010 |
Michael Cera |
Scott Pilgrim vs. the World |
Scott Pilgrim
|
| Steve Carell |
Dinner for Schmucks |
Barry Speck
|
| Romain Duris |
Heartbreaker |
Alex Lippi
|
| Andy García |
City Island |
Vince Rizzo
|
| Jake Gyllenhaal |
Love & Other Drugs |
Jamie Randall
|
| John Malkovich |
Red |
Marvin Boggs
|
| John C. Reilly |
Cyrus |
John Kilpatrick
|
