| Year | Title | Accolade | Results | Ref |
| 2004 | Sideways | Award Circuit Community Award, Best Supporting Actor | Nominated | |
| Award Circuit Community Award, Best Cast Ensemble | Won |
| Boston Society Film Critics Award, Best Supporting Actor | Won | |
| Boston Society Film Critics Award, Best Cast Ensemble | Won |
| Chicago Film Critics Association Award, Best Supporting Actor | Won | |
| Florida Film Critics Circle Award, Best Supporting Actor | Won | |
| Golden Schmoes Award, Best Supporting Actor of the Year | Nominated | |
| Kansas City Film Critics Circle Award, Best Supporting Actor | Won | |
| Los Angeles Film Critics Association Award, Best Supporting Actor | Won | |
| National Board of Review Award, Best Supporting Actor | Won | |
| New York Film Critics Circle Award, Best Supporting Actor | Nominated | |
| New York Film Critics Online Award, Best Supporting Actor | Won | |
| Phoenix Film Critics Society Award, Best Supporting Actor | Won | |
| Phoenix Film Critics Society Award, Best Ensemble Acting | Won |
| San Francisco Film Critics Circle Award, Best Supporting Actor | Won | |
| Seattle Film Critics Award, Best Supporting Actor | Won | |
| Southeastern Film Critics Association Award, Best Supporting Actor | Won | |
| St. Louis Film Critics Association Award, Best Supporting Actor | Won | |
| Utah Film Critics Association Award, Best Supporting Actor | Nominated | |
| Village Voice Film Poll Award, Best Supporting Performance | Nominated | |
| Washing D.C. Area Film Critics Association Award, Best Supporting Actor | Nominated | |
| 2005 | Academy Award, Best Supporting Actor | Nominated | |
| Critics Choice Award, Best Supporting Actor | Won | |
| Critics Choice Award, Best Ensemble | Nominated |
| Dallas-Fort Worth Film Critics Association Award, Best Supporting Actor | Won | |
| Gold Derby Award, Best Supporting Actor | Nominated | |
| Gold Derby Award, Best Ensemble | Nominated |
| Golden Globe Award, Best Supporting Actor in a Motion Picture | Nominated | |
| Independent Spirit Award, Best Supporting Male | Won | |
| International Online Cinema Award, Best Supporting Actor | Nominated | |
| Iowa Film Critics Award, Best Supporting Actor | Won | |
| National Society of Film Critics Award, Best Supporting Actor | Won | |
| Online Film & Television Association Award, Best Breakthrough Performance – Male | Won | |
| Online Film & Television Association Award, Best Supporting Actor | Nominated |
| Online Film Critics Society Award, Best Supporting Actor | Won | |
| Satellite Award, Best Supporting Actor in a Motion Picture, Comedy or Musical | Won | |
| Screen Actors Guild Award, Outstanding Performance by a Male Actor in a Supporting Role | Nominated | |
| Screen Actors Guild Award, Outstanding Performance by an Ensemble in a Motion Picture | Won |
| Vancouver Film Critics Circle Award, Best Supporting Actor | Nominated | |
| 2007 | Broken Trail | Gold Derby Award, Best Lead Actor in a Television Movie/Miniseries | Nominated | |
| Golden Globe Award, Best Supporting Actor in a Series, Miniseries or Motion Picture Made for Television | Nominated | |
| Monte-Carlo Television Festival Award, Mini-Series – Best Performance by an Actor | Nominated | |
| Online Film & Television Association Award, Best Supporting Actor in a Motion Picture or Miniseries | Won | |
| Primetime Emmy Award, Outstanding Supporting Actor in a Miniseries or Movie | Won | |
| Screen Actors Guild Award, Outstanding Performance by a Male Actor in a Television Movie or Miniseries | Nominated | |
| Spider-Man 3 | Teen Choice Award, Choice Movie – Rumble (shared with Tobey Maguire, James Franco, Topher Grace) | Nominated | |
| Broken Trail | Western Heritage Award, Outstanding Television Feature Film | Won | |
| 2014 | Whitewash | Vancouver Film Critics Circle Award, Best Actor in a Canadian Film | Nominated | |