4 wins & 24 nominations
- 2007 Nominee Critics Choice Award
- Best Acting Ensemble
Shared with: Lindsay Lohan · Meryl Streep · Virginia Madsen · Tommy Lee Jones · Maya Rudolph · Lily Tomlin · Kevin Kline · Woody Harrelson · John C. Reilly
- 2006 Nominee Gotham Independent Film Award
- Best Ensemble Performance
Shared with: Woody Harrelson · Tommy Lee Jones · Kevin Kline · Lindsay Lohan · Virginia Madsen · John C. Reilly · Maya Rudolph · Meryl Streep · Lily Tomlin · L.Q. Jones · Sue Scott · Tim Russell
- 2000 Nominee Grammy
- Best Spoken Comedy Album
For "A Prairie Home Companion - 25th Anniversary Collection"
- 2007 Nominee OFTA Film Award
- Best Music, Adapted Song
For the traditional song "Frankie and Johnny".Shared with: Lindsay Lohan
- 2016 Nominee Voice Arts Award
- Outstanding Spoken Word or Storytelling - Best Performance
for "The Road Home" by Garrison Keillor - 2015 Winner Voice Arts Award
- Audiobook Narration - Author Performance, Best Voiceover
for "O, What a Luxury: Verses Lyrical, Vulgar, Pathetic & Profound" by Garrison Keillor
- 2007 Nominee Gold Derby Film Award
- Ensemble Cast
Shared with: Woody Harrelson · L.Q. Jones · Tommy Lee Jones · Kevin Kline · Lindsay Lohan · Virginia Madsen · John C. Reilly · Maya Rudolph · Meryl Streep · Lily Tomlin
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