# Chicago Film Critics Association Award for Best Supporting Actor

The Chicago Film Critics Association Award for Best Supporting Actor is an annual award given by the Chicago Film Critics Association.

## Winners
### 1980s

| Year | Winner and nominees | Film | Role |
| 1988 | Martin Landau | Tucker: The Man and His Dream | Abe Karatz |
| 1989 | Danny Aiello | Do the Right Thing | Sal |
| 1989 | Marlon Brando | A Dry White Season | Joe Bella |
| 1989 | Morgan Freeman | Glory | Sergeant Major John Rawlins |
| 1989 | John Goodman | Sea of Love | Det. Sherman Touhey |
| 1989 | Lance Henriksen | Johnny Handsome | Rafe Garrett |
| 1989 | Jack Nicholson | Batman | Jack Napier / The Joker |
| 1989 | Denzel Washington | Glory | Private Silas Trip |

### 1990s

| Year | Winner and nominees | Film | Role |
| 1990 | Joe Pesci | Goodfellas | Tommy DeVito |
| 1991 | Harvey Keitel | Bugsy | Mickey Cohen |
| 1991 | Danny Aiello | Once Around | Joe Bella |
| 1991 | Ice Cube | Boyz n the Hood | Darrin "Doughboy" Baker |
| 1991 | Laurence Fishburne | Boyz n the Hood | Furious Styles |
| 1991 | John Goodman | Barton Fink | Charlie Meadows |
| 1991 | Samuel L. Jackson | Jungle Fever | "Gator" Purify |
| 1991 | Michael Lerner | Barton Fink | Jack Lipnick |
| 1991 | Jack Palance | City Slickers | Curly Washburn |
| 1991 | Alan Rickman | Robin Hood: Prince of Thieves | Sheriff of Nottingham |
| 1992 | Jack Nicholson | A Few Good Men | Colonel Nathan Jessup |
| 1992 | Al Freeman Jr. | Malcolm X | Elijah Muhammad |
| 1992 | Jeff Goldblum | Deep Cover | David Jason |
| 1992 | Gene Hackman | Unforgiven | Little Bill Daggett |
| 1992 | Al Pacino | Glengarry Glen Ross | Ricky Roma |
| 1993 | Ralph Fiennes | Schindler's List | Amon Göth |
| 1993 | Jeff Daniels | Gettysburg | Colonel Joshua Chamberlain |
| 1993 | Tommy Lee Jones | The Fugitive | Marshal Samuel Gerard |
| 1993 | John Malkovich | In the Line of Fire | Mitch Leary |
| 1993 | Sean Penn | Carlito's Way | David Kleinfeld |
| 1994 | Martin Landau | Ed Wood | Bela Lugosi |
| 1994 | Morgan Freeman | The Shawshank Redemption | Ellis Boyd "Red" Redding |
| 1994 | Anthony Hopkins | The Road to Wellville | Dr. John Harvey Kellogg |
| 1994 | Chazz Palminteri | Bullets Over Broadway | Cheech |
| 1994 | Gary Sinise | Forrest Gump | Lt. Dan Taylor |
| 1994 | John Turturro | Quiz Show | Herb Stempel |
| 1995 | Kevin Spacey | The Usual Suspects | Roger "Verbal" Kint |
| 1995 | Don Cheadle | Devil in a Blue Dress | Mouse Alexander |
| 1995 | Gene Hackman | Get Shorty | Harry Zimm |
| 1995 | Ed Harris | Apollo 13 | Gene Kranz |
| 1995 | Delroy Lindo | Clockers | Rodney Little |
| 1996 | Cuba Gooding Jr. | Jerry Maguire | Rod Tidwell |
| 1996 | Steve Buscemi | Fargo | Carl Showalter |
| 1996 | Nathan Lane | The Birdcage | Albert Goldman |
| 1996 | Edward Norton | Primal Fear | Aaron Stampler |
| 1996 | James Woods | Ghosts of Mississippi | Byron De La Beckwith |
| 1997 | Burt Reynolds | Boogie Nights | Jack Horner |
| 1997 | Robert Forster | Jackie Brown | Max Cherry |
| 1997 | Anthony Hopkins | Amistad | John Quincy Adams |
| 1997 | Greg Kinnear | As Good as It Gets | Simon Bishop |
| 1997 | Kevin Spacey | L.A. Confidential | Det. Sgt. Jack Vincennes |
| 1998 | Billy Bob Thornton | A Simple Plan | Jacob Mitchell |
| 1998 | Michael Caine | Little Voice | Ray Say |
| 1998 | Robert Duvall | A Civil Action | Jerome Facher |
| 1998 | Bill Murray | Rushmore | Herman Blume |
| 1998 | Nick Nolte | The Thin Red Line | Lt. Col. Gordon Tall |
| 1999 | Tom Cruise | Magnolia | Frank T.J. Mackey |
| 1999 | Michael Clarke Duncan | The Green Mile | John Coffey |
| 1999 | John Malkovich | Being John Malkovich | John Horatio Malkovich |
| 1999 | Haley Joel Osment | The Sixth Sense | Cole Sear |
| 1999 | Christopher Plummer | The Insider | Mike Wallace |

### 2000s

| Year | Winner and nominees | Film | Role |
| 2000 | Benicio del Toro | Traffic | Javier Rodriguez |
| 2000 | Jack Black | High Fidelity | Barry |
| 2000 | Willem Dafoe | Shadow of the Vampire | Max Schreck |
| 2000 | Albert Finney | Erin Brockovich | Edward L. Masry |
| 2000 | Philip Seymour Hoffman | Almost Famous | Lester Bangs |
| 2001 | Steve Buscemi | Ghost World | Seymour |
| 2001 | Ben Kingsley | Sexy Beast | Don Logan |
| 2001 | Jude Law | A.I. Artificial Intelligence | Gigolo Joe |
| 2001 | Tony Shalhoub | The Man Who Wasn't There | Freddy Riedenschneider |
| 2001 | Jon Voight | Ali | Howard Cosell |
| 2002 | Dennis Quaid | Far from Heaven | Frank Whitaker |
| 2002 | Chris Cooper | Adaptation | John Laroche |
| 2002 | Willem Dafoe | Auto Focus | John Henry Carpenter |
| 2002 | Alfred Molina | Frida | Diego Rivera |
| 2002 | Paul Newman | Road to Perdition | John Rooney |
| 2003 | Tim Robbins | Mystic River | Dave Boyle |
| 2003 | Sean Astin | The Lord of the Rings: The Return of the King | Samwise Gamgee |
| 2003 | Alec Baldwin | The Cooler | Shelly Kaplow |
| 2003 | Benicio del Toro | 21 Grams | Jack Jordan |
| 2003 | Peter Sarsgaard | Shattered Glass | Chuck Lane |
| 2003 | Andy Serkis | The Lord of the Rings: The Return of the King | Sméagol/Gollum |
| 2004 | Thomas Haden Church | Sideways | Jack |
| 2005 | Mickey Rourke | Sin City | Marv |
| 2005 | Matt Dillon | Crash | Officer John Ryan |
| 2005 | Terrence Howard | Crash | Cameron Thayer |
| 2005 | Paul Giamatti | Cinderella Man | Joe Gould |
| 2005 | Jake Gyllenhaal | Brokeback Mountain | Jack Twist |
| 2005 | Donald Sutherland | Pride & Prejudice | Mr. Bennet |
| 2006 | Jackie Earle Haley | Little Children | Ronald J. McGorvey |
| 2006 | Ben Affleck | Hollywoodland | George Reeves |
| 2006 | Eddie Murphy | Dreamgirls | James "Thunder" Early |
| 2006 | Jack Nicholson | The Departed | Frank Costello |
| 2006 | Brad Pitt | Babel | Richard Jones |
| 2006 | Michael Sheen | The Queen | Tony Blair |
| 2007 | Javier Bardem | No Country for Old Men | Anton Chigurh |
| 2007 | Casey Affleck | The Assassination of Jesse James by the Coward Robert Ford | Robert Ford |
| 2007 | Philip Seymour Hoffman | Charlie Wilson's War | Gust Avrakotos |
| 2007 | Hal Holbrook | Into the Wild | Ron Franz |
| 2007 | Tom Wilkinson | Michael Clayton | Arthur Edens |
| 2008 | Heath Ledger (posthumous) | The Dark Knight | The Joker |
| 2008 | Robert Downey Jr. | Tropic Thunder | Kirk Lazarus |
| 2008 | Philip Seymour Hoffman | Doubt | Father Brendan Flynn |
| 2008 | Bill Irwin | Rachel Getting Married | Paul |
| 2008 | Michael Shannon | Revolutionary Road | John Givings, Jr. |
| 2009 | Christoph Waltz | Inglourious Basterds | Col. Hans Landa |
| 2009 | Peter Capaldi | In the Loop | Malcolm Tucker |
| 2009 | Woody Harrelson | The Messenger | Capt. Tony Stone |
| 2009 | Christian McKay | Me and Orson Welles | Orson Welles |
| 2009 | Stanley Tucci | The Lovely Bones | George Harvey |

### 2010s

| Year | Winner and nominees | Film | Role |
| 2010 | Christian Bale | The Fighter | Dicky Eklund |
| 2010 | Andrew Garfield | The Social Network | Eduardo Saverin |
| 2010 | John Hawkes | Winter's Bone | Teardrop Dolly |
| 2010 | Mark Ruffalo | The Kids Are All Right | Paul Hatfield |
| 2010 | Geoffrey Rush | The King's Speech | Lionel Logue |
| 2011 | Albert Brooks | Drive | Bernie Rose |
| 2011 | Nick Nolte | Warrior | Paddy Conlon |
| 2011 | Patton Oswalt | Young Adult | Matt Freehauf |
| 2011 | Brad Pitt | The Tree of Life | Mr. O'Brien |
| 2011 | Christopher Plummer | Beginners | Hal Fields |
| 2012 | Philip Seymour Hoffman | The Master | Lancaster Dodd |
| 2012 | Jason Clarke | Zero Dark Thirty | Dan |
| 2012 | Leonardo DiCaprio | Django Unchained | Calvin Candie |
| 2012 | Dwight Henry | Beasts of the Southern Wild | Wink |
| 2012 | Tommy Lee Jones | Lincoln | Thaddeus Stevens |
| 2013 | Jared Leto | Dallas Buyers Club | Rayon |
| 2013 | Barkhad Abdi | Captain Phillips | Abduwali Muse |
| 2013 | Michael Fassbender | 12 Years a Slave | Edwin Epps |
| 2013 | James Franco | Spring Breakers | Alien |
| 2013 | James Gandolfini | Enough Said | Albert |
| 2014 | J. K. Simmons | Whiplash | Terence Fletcher |
| 2014 | Josh Brolin | Inherent Vice | Lt. Det. Christian "Bigfoot" Bjornsen |
| 2014 | Ethan Hawke | Boyhood | Mason Evans, Sr. |
| 2014 | Edward Norton | Birdman | Mike Shiner |
| 2014 | Mark Ruffalo | Foxcatcher | Dave Schultz |
| 2015 | Benicio Del Toro | Sicario | Alejandro |
| 2015 | Sam Elliott | Grandma | Karl |
| 2015 | Mark Rylance | Bridge of Spies | Rudolf Abel |
| 2015 | Michael Shannon | 99 Homes | Rick Carver |
| 2015 | Sylvester Stallone | Creed | Rocky Balboa |
| 2016 | Mahershala Ali | Moonlight | Juan |
| 2016 | Alden Ehrenreich | Hail, Caesar! | Hobie Doyle |
| 2016 | Ben Foster | Hell or High Water | Tanner Howard |
| 2016 | Lucas Hedges | Manchester by the Sea | Patrick Chandler |
| 2016 | Trevante Rhodes | Moonlight | Chiron/"Black" |
| 2016 | Michael Shannon | Nocturnal Animals | Detective Bobby Andes |
| 2017 | Willem Dafoe | The Florida Project | Bobby Hicks |
| 2017 | Armie Hammer | Call Me by Your Name | Oliver |
| 2017 | Jason Mitchell | Mudbound | Ronsel Jackson |
| 2017 | Sam Rockwell | Three Billboards Outside Ebbing, Missouri | Jason Dixon |
| 2017 | Michael Stuhlbarg | Call Me by Your Name | Mr. Perlman |
| 2018 | Richard E. Grant | Can You Ever Forgive Me? | Jack Hock |
| 2018 | Mahershala Ali | Green Book | Dr. Don Shirley |
| 2018 | Timothée Chalamet | Beautiful Boy | Nic Scheff |
| 2018 | Michael B. Jordan | Black Panther | Erik Killmonger |
| 2018 | Steven Yeun | Burning | Ben |
| 2019 | Brad Pitt | Once Upon a Time in Hollywood | Cliff Booth |
| 2019 | Tom Hanks | A Beautiful Day in the Neighborhood | Fred Rogers |
| 2019 | Shia LaBeouf | Honey Boy | James Lort |
| 2019 | Al Pacino | The Irishman | Jimmy Hoffa |
| 2019 | Joe Pesci | The Irishman | Russell Bufalino |

### 2020s

| Year | Winner and nominees | Film | Role |
| 2020 | Paul Raci | Sound of Metal | Joe |
| 2020 | Chadwick Boseman | Da 5 Bloods | "Stormin'" Norman Earl Holloway |
| 2020 | Bill Murray | On the Rocks | Felix Keane |
| 2020 | Leslie Odom Jr. | One Night in Miami... | Sam Cooke |
| 2020 | David Strathairn | Nomadland | David |
| 2021 | Kodi Smit-McPhee | The Power of the Dog | Peter Gordon |
| 2021 | Bradley Cooper | Licorice Pizza | Jon Peters |
| 2021 | Colman Domingo | Zola | Abegunde “X” Olawale |
| 2021 | Mike Faist | West Side Story | Riff |
| 2021 | Jeffrey Wright | The French Dispatch | Roebuck Wright |
| 2022 | Ke Huy Quan | Everything Everywhere All at Once | Waymond Wang |
| 2022 | Brendan Gleeson | The Banshees of Inisherin | Colm Doherty |
| 2022 | Brian Tyree Henry | Causeway | James Aucoin |
| 2022 | Barry Keoghan | The Banshees of Inisherin | Dominic Kearney |
| 2022 | Mark Rylance | Bones and All | Sully |
| 2023 | Charles Melton | May December | Joe Yoo |
| 2023 | Robert Downey Jr. | Oppenheimer | Lewis Strauss |
| 2023 | Ryan Gosling | Barbie | Ken |
| 2023 | Glenn Howerton | BlackBerry | Jim Balsillie |
| 2023 | Mark Ruffalo | Poor Things | Duncan Wedderburn |
| 2024 | Kieran Culkin | A Real Pain | Benji Kaplan |
| 2024 | Yura Borisov | Anora | Igor |
| 2024 | Clarence Maclin | Sing Sing | Himself |
| 2024 | Guy Pearce | The Brutalist | Harrison Lee Van Buren |
| 2024 | Adam Pearson | A Different Man | Oswald |