# Chicago Film Critics Association Award for Best Actor

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

## Winners
### 1980s

| Year | Winner and nominees | Film | Role |
| 1988 | Jeremy Irons | Dead Ringers | Beverly Mantle / Elliot Mantle |
| 1989 | Tom Cruise | Born on the Fourth of July | Ron Kovic |
| 1989 | Kenneth Branagh | Henry V | Henry V |
| 1989 | Daniel Day-Lewis | My Left Foot | Christy Brown |
| 1989 | Martin Landau | Crimes and Misdemeanors | Judah Rosenthal |
| 1989 | James Spader | Sex, Lies, and Videotape | Graham Dalton |

### 1990s

| Year | Winner and nominees | Film | Role |
| 1990 | Jeremy Irons | Reversal of Fortune | Claus von Bülow |
| 1991 | Anthony Hopkins | The Silence of the Lambs | Hannibal Lecter |
| 1991 | Warren Beatty | Bugsy | Bugsy Siegel |
| 1991 | William Hurt | The Doctor | Dr. Jack MacKee |
| 1991 | Val Kilmer | The Doors | Jim Morrison |
| 1991 | Joe Mantegna | Homicide | Bobby Gold |
| 1991 | Nick Nolte | The Prince of Tides | Tom Wingo |
| 1991 | John Turturro | Barton Fink | Barton Fink |
| 1992 | Denzel Washington | Malcolm X | Malcolm X |
| 1992 | Robert Downey Jr. | Chaplin | Charlie Chaplin |
| 1992 | Clint Eastwood | Unforgiven | William 'Will' Munny |
| 1992 | Al Pacino | Scent of a Woman | Frank Slade |
| 1992 | Tim Robbins | The Player | Griffin Mill |
| 1993 | Liam Neeson | Schindler's List | Oskar Schindler |
| 1993 | Jeff Bridges | Fearless | Max Klein |
| 1993 | Daniel Day-Lewis | The Age of Innocence | Newland Archer |
| 1993 | Laurence Fishburne | What's Love Got to Do with It | Ike Turner |
| 1993 | Tom Hanks | Philadelphia | Andrew Beckett |
| 1993 | Anthony Hopkins | The Remains of the Day | James Stevens |
| 1994 | Tom Hanks | Forrest Gump | Forrest Gump |
| 1994 | Johnny Depp | Ed Wood | Ed Wood |
| 1994 | Samuel L. Jackson | Pulp Fiction | Jules Winnfield |
| 1994 | Tommy Lee Jones | Cobb | Ty Cobb |
| 1994 | John Travolta | Pulp Fiction | Vincent Vega |
| 1995 | Nicolas Cage | Leaving Las Vegas | Ben Sanderson |
| 1995 | Morgan Freeman | Seven | Detective Lt. William Somerset |
| 1995 | Anthony Hopkins | Nixon | Richard Nixon |
| 1995 | Sean Penn | Dead Man Walking | Matthew Poncelet |
| 1995 | Denzel Washington | Devil in a Blue Dress | Easy Rawlins |
| 1996 | Billy Bob Thornton | Sling Blade | Karl Childers |
| 1996 | Kenneth Branagh | Hamlet | Hamlet |
| 1996 | William H. Macy | Fargo | Jerry Lundegaard |
| 1996 | Liam Neeson | Michael Collins | Michael Collins |
| 1996 | Geoffrey Rush | Shine | David Helfgott |
| 1996 | Denzel Washington | Courage Under Fire | Lt. Colonel Nathaniel Serling |
| 1997 | Robert Duvall | The Apostle | Euliss Dewey/The Apostle |
| 1997 | Peter Fonda | Ulee's Gold | Ulysses 'Ulee' Jackson |
| 1997 | Ian Holm | The Sweet Hereafter | Mitchell Stephens |
| 1997 | Jack Nicholson | As Good as It Gets | Melvin Udall |
| 1997 | Al Pacino | Donnie Brasco | Benjamin 'Lefty' Ruggiero |
| 1998 | Ian McKellen | Gods and Monsters | James Whale |
| 1998 | Roberto Benigni | Life Is Beautiful | Guido Orefice |
| 1998 | Jim Carrey | The Truman Show | Truman Burbank |
| 1998 | Tom Hanks | Saving Private Ryan | Captain John H. Miller |
| 1998 | Edward Norton | American History X | Derek Vinyard |
| 1999 | Kevin Spacey | American Beauty | Lester Burnham |
| 1999 | Jim Broadbent | Topsy-Turvy | W. S. Gilbert |
| 1999 | Russell Crowe | The Insider | Jeffrey Wigand |
| 1999 | Richard Farnsworth | The Straight Story | Alvin Straight |
| 1999 | Denzel Washington | The Hurricane | Rubin "The Hurricane" Carter |

### 2000s

| Year | Winner and nominees | Film | Role |
| 2000 | Tom Hanks | Cast Away | Chuck Noland |
| 2000 | Javier Bardem | Before Night Falls | Reinaldo Arenas |
| 2000 | Michael Douglas | Wonder Boys | Prof. Grady Tripp |
| 2000 | Mark Ruffalo | You Can Count on Me | Terry Prescott |
| 2000 | Geoffrey Rush | Quills | Marquis de Sade |
| 2001 | Gene Hackman | The Royal Tenenbaums | Royal Tenenbaum |
| 2001 | Russell Crowe | A Beautiful Mind | John Nash |
| 2001 | John Cameron Mitchell | Hedwig and the Angry Inch | Hansel Schmidt/Hedwig Robinson |
| 2001 | Guy Pearce | Memento | Leonard Shelby |
| 2001 | Denzel Washington | Training Day | Alonzo Harris |
| 2001 | Tom Wilkinson | In the Bedroom | Matt Fowler |
| 2002 | Daniel Day-Lewis | Gangs of New York | William "Bill the Butcher" Cutting |
| 2002 | Adrien Brody | The Pianist | Władysław Szpilman |
| 2002 | Nicolas Cage | Adaptation | Charlie and Donald Kaufman |
| 2002 | Hugh Grant | About a Boy | Will Freeman |
| 2002 | Jack Nicholson | About Schmidt | Warren R. Schmidt |
| 2003 | Bill Murray | Lost in Translation | Bob Harris |
| 2003 | Johnny Depp | Pirates of the Caribbean: The Curse of the Black Pearl | Captain Jack Sparrow |
| 2003 | Paul Giamatti | American Splendor | Harvey Pekar |
| 2003 | Ben Kingsley | House of Sand and Fog | Colonel Massoud Amir Behrani |
| 2003 | Sean Penn | Mystic River | Jimmy Markum |
| 2004 | Paul Giamatti | Sideways | Miles Raymond |
| 2005 | Philip Seymour Hoffman | Capote | Truman Capote |
| 2005 | Terrence Howard | Hustle & Flow | DJay |
| 2005 | Heath Ledger | Brokeback Mountain | Ennis Del Mar |
| 2005 | Joaquin Phoenix | Walk the Line | Johnny Cash |
| 2005 | David Strathairn | Good Night, and Good Luck | Edward R. Murrow |
| 2006 | Forest Whitaker | The Last King of Scotland | Idi Amin |
| 2006 | Leonardo DiCaprio | The Departed | Billy Costigan |
| 2006 | Ryan Gosling | Half Nelson | Dan Dunne |
| 2006 | Peter O'Toole | Venus | Maurice |
| 2006 | Will Smith | The Pursuit of Happyness | Chris Gardner |
| 2007 | Daniel Day-Lewis | There Will Be Blood | Daniel Plainview |
| 2007 | George Clooney | Michael Clayton | Michael Clayton |
| 2007 | Ryan Gosling | Lars and the Real Girl | Lars Lindstrom |
| 2007 | Frank Langella | Starting Out in the Evening | Leonard Schiller |
| 2007 | Viggo Mortensen | Eastern Promises | Nikolai Luzhin |
| 2008 | Mickey Rourke | The Wrestler | Randy Robinson |
| 2008 | Clint Eastwood | Gran Torino | Walt Kowalski |
| 2008 | Richard Jenkins | The Visitor | Walter Vale |
| 2008 | Frank Langella | Frost/Nixon | Richard Nixon |
| 2008 | Sean Penn | Milk | Harvey Milk |
| 2009 | Jeremy Renner | The Hurt Locker | SFC. William James |
| 2009 | Jeff Bridges | Crazy Heart | Bad Blake |
| 2009 | George Clooney | Up in the Air | Ryan Bingham |
| 2009 | Matt Damon | The Informant! | Mark Whitacre |
| 2009 | Michael Stuhlbarg | A Serious Man | Larry Gopnik |

### 2010s

| Year | Winner and nominees | Film | Role |
| 2010 | Colin Firth | The King's Speech | King George VI |
| 2010 | Jeff Bridges | True Grit | Rooster Cogburn |
| 2010 | Jesse Eisenberg | The Social Network | Mark Zuckerberg |
| 2010 | James Franco | 127 Hours | Aron Ralston |
| 2010 | Ryan Gosling | Blue Valentine | Dean |
| 2011 | Michael Shannon | Take Shelter | Curtis LaForche |
| 2011 | George Clooney | The Descendants | Matt King |
| 2011 | Jean Dujardin | The Artist | George Valentin |
| 2011 | Michael Fassbender | Shame | Brandon Sullivan |
| 2011 | Gary Oldman | Tinker Tailor Soldier Spy | George Smiley |
| 2012 | Daniel Day-Lewis | Lincoln | Abraham Lincoln |
| 2012 | John Hawkes | The Sessions | Mark O'Brien |
| 2012 | Denis Lavant | Holy Motors | Mr. Oscar |
| 2012 | Joaquin Phoenix | The Master | Freddie Quell |
| 2012 | Denzel Washington | Flight | Whip Whitaker |
| 2013 | Chiwetel Ejiofor | 12 Years a Slave | Solomon Northup |
| 2013 | Bruce Dern | Nebraska | Woody Grant |
| 2013 | Oscar Isaac | Inside Llewyn Davis | Llewyn Davis |
| 2013 | Matthew McConaughey | Dallas Buyers Club | Ron Woodroof |
| 2013 | Robert Redford | All Is Lost | Our Man |
| 2014 | Michael Keaton | Birdman | Riggan Thomson / Birdman |
| 2014 | Benedict Cumberbatch | The Imitation Game | Alan Turing |
| 2014 | Jake Gyllenhaal | Nightcrawler | Lou Bloom |
| 2014 | David Oyelowo | Selma | Martin Luther King Jr. |
| 2014 | Eddie Redmayne | The Theory of Everything | Stephen Hawking |
| 2015 | Leonardo DiCaprio | The Revenant | Hugh Glass |
| 2015 | Christopher Abbott | James White | James White |
| 2015 | Michael Fassbender | Steve Jobs | Steve Jobs |
| 2015 | Eddie Redmayne | The Danish Girl | Lili Elbe / Einar Wegener |
| 2015 | Jason Segel | The End of the Tour | David Foster Wallace |
| 2016 | Casey Affleck | Manchester by the Sea | Lee Chandler |
| 2016 | Adam Driver | Paterson | Paterson |
| 2016 | Joel Edgerton | Loving | Richard Loving |
| 2016 | Colin Farrell | The Lobster | David |
| 2016 | Denzel Washington | Fences | Troy Maxson |
| 2017 | Timothée Chalamet | Call Me by Your Name | Elio Perlman |
| 2017 | Daniel Day-Lewis | Phantom Thread | Reynolds Woodcock |
| 2017 | James Franco | The Disaster Artist | Tommy Wiseau |
| 2017 | Gary Oldman | Darkest Hour | Winston Churchill |
| 2017 | Harry Dean Stanton | Lucky | Lucky |
| 2018 | Ethan Hawke | First Reformed | Ernst Toller |
| 2018 | Christian Bale | Vice | Dick Cheney |
| 2018 | Bradley Cooper | A Star Is Born | Jackson Maine |
| 2018 | Rami Malek | Bohemian Rhapsody | Freddie Mercury |
| 2018 | Joaquin Phoenix | You Were Never Really Here | Joe |
| 2019 | Adam Driver | Marriage Story | Charlie Barber |
| 2019 | Antonio Banderas | Pain and Glory | Salvador Mallo |
| 2019 | Robert De Niro | The Irishman | Frank Sheeran |
| 2019 | Joaquin Phoenix | Joker | Arthur Fleck / Joker |
| 2019 | Adam Sandler | Uncut Gems | Howard Ratner |

### 2020s

| Year | Winner and nominees | Film | Role |
| 2020 | Chadwick Boseman | Ma Rainey's Black Bottom | Levee Green |
| 2020 | Riz Ahmed | Sound of Metal | Ruben Stone |
| 2020 | Anthony Hopkins | The Father | Anthony |
| 2020 | Delroy Lindo | Da 5 Bloods | Paul |
| 2020 | Steven Yeun | Minari | Jacob Yi |
| 2021 | Benedict Cumberbatch | The Power of the Dog | Phil Burbank |
| 2021 | Nicolas Cage | Pig | Robin "Rob" Feld |
| 2021 | Andrew Garfield | tick, tick... BOOM! | Jonathan Larson |
| 2021 | Hidetoshi Nishijima | Drive My Car | Yūsuke Kafuku |
| 2021 | Simon Rex | Red Rocket | Mikey Saber |
| 2022 | Colin Farrell | The Banshees of Inisherin | Pádraic Súilleabháin |
| 2022 | Austin Butler | Elvis | Elvis Presley |
| 2022 | Brendan Fraser | The Whale | Charlie |
| 2022 | Paul Mescal | Aftersun | Calum |
| 2022 | Bill Nighy | Living | Mr. Williams |
| 2023 | Paul Giamatti | The Holdovers | Paul Hunham |
| 2023 | Leonardo DiCaprio | Killers of the Flower Moon | Ernest Burkhart |
| 2023 | Cillian Murphy | Oppenheimer | J. Robert Oppenheimer |
| 2023 | Andrew Scott | All of Us Strangers | Adam |
| 2023 | Teo Yoo | Past Lives | Hae Sung |
| 2024 | Adrien Brody | The Brutalist | László Tóth |
| 2024 | Timothée Chalamet | A Complete Unknown | Bob Dylan |
| 2024 | Colman Domingo | Sing Sing | John "Divine G" Whitfield |
| 2024 | Ralph Fiennes | Conclave | Thomas Cardinal Lawrence |
| 2024 | Keith Kupferer | Ghostlight | Dan Mueller |