| Chicago Film Critics Association Award for Best Actor | |
| Awarded For: | Best Performance by an Actor in a Leading Role |
| Country: | United States |
| Image Upright: | 0.7 |
| Year: | Jeremy Irons Dead Ringers (1988) |
| Holder: | Paul Giamatti The Holdovers (2023) |
The Chicago Film Critics Association Award for Best Actor is an annual award given by the Chicago Film Critics Association.
| 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 |
| Henry V | Henry V | ||
| My Left Foot | Christy Brown | ||
| Crimes and Misdemeanors | Judah Rosenthal | ||
| Sex, Lies, and Videotape | Graham Dalton | ||
| 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 |
| Bugsy | Bugsy Siegel | ||
| The Doctor | Dr. Jack MacKee | ||
| The Doors | Jim Morrison | ||
| Homicide | Bobby Gold | ||
| The Prince of Tides | Tom Wingo | ||
| Barton Fink | Barton Fink | ||
| 1992 | Denzel Washington | Malcolm X | Malcolm X |
| Chaplin | Charlie Chaplin | ||
| Unforgiven | William 'Will' Munny | ||
| Scent of a Woman | Frank Slade | ||
| The Player | Griffin Mill | ||
| 1993 | Liam Neeson | Schindler's List | Oskar Schindler |
| Fearless | Max Klein | ||
| The Age of Innocence | Newland Archer | ||
| What's Love Got to Do with It | Ike Turner | ||
| Philadelphia | Andrew Beckett | ||
| The Remains of the Day | James Stevens | ||
| 1994 | Tom Hanks | Forrest Gump | Forrest Gump |
| Ed Wood | Ed Wood | ||
| Pulp Fiction | Jules Winnfield | ||
| Cobb | Ty Cobb | ||
| Pulp Fiction | Vincent Vega | ||
| 1995 | Nicolas Cage | Leaving Las Vegas | Ben Sanderson |
| Seven | Detective Lt. William Somerset | ||
| Nixon | Richard Nixon | ||
| Dead Man Walking | Matthew Poncelet | ||
| Devil in a Blue Dress | Easy Rawlins | ||
| 1996 | Billy Bob Thornton | Sling Blade | Karl Childers |
| Hamlet | Hamlet | ||
| Fargo | Jerry Lundegaard | ||
| Michael Collins | Michael Collins | ||
| Shine | David Helfgott | ||
| Courage Under Fire | Lt. Colonel Nathaniel Serling | ||
| 1997 | Robert Duvall | The Apostle | Euliss Dewey/The Apostle |
| Ulee's Gold | Ulysses 'Ulee' Jackson | ||
| The Sweet Hereafter | Mitchell Stephens | ||
| As Good as It Gets | Melvin Udall | ||
| Donnie Brasco | Benjamin 'Lefty' Ruggiero | ||
| 1998 | Ian McKellen | Gods and Monsters | James Whale |
| Life Is Beautiful | Guido Orefice | ||
| The Truman Show | Truman Burbank | ||
| Saving Private Ryan | Captain John H. Miller | ||
| American History X | Derek Vinyard | ||
| 1999 | Kevin Spacey | American Beauty | Lester Burnham |
| Topsy-Turvy | W. S. Gilbert | ||
| The Insider | Jeffrey Wigand | ||
| The Straight Story | Alvin Straight | ||
| The Hurricane | Rubin "The Hurricane" Carter |
| Year | Winner and nominees | Film | Role |
|---|---|---|---|
| 2020[3] | Chadwick Boseman | Ma Rainey's Black Bottom | Levee Green |
| Riz Ahmed | Sound of Metal | Ruben Stone | |
| Anthony | |||
| Da 5 Bloods | Paul | ||
| Jacob Yi | |||
| 2021[4] | Benedict Cumberbatch | The Power of the Dog | Phil Burbank |
| Pig | Robin "Rob" Feld | ||
| Jonathan Larson | |||
| Drive My Car | Yūsuke Kafuku | ||
| Mikey Saber | |||
| 2022 | Colin Farrell | The Banshees of Inisherin | Pádraic Súilleabháin |
| Elvis | Elvis Presley | ||
| The Whale | Charlie | ||
| Aftersun | Calum | ||
| Mr. Williams | |||
| 2023 | Paul Giamatti | The Holdovers | Paul Hunham |
| Killers of the Flower Moon | Ernest Burkhart | ||
| Oppenheimer | J. Robert Oppenheimer | ||
| Andrew Scott | All of Us Strangers | Adam | |
| Past Lives | Hae Sung |