38 wins & 119 nominations
- 2001 Nominee Blockbuster Entertainment Award
- Favorite Supporting Actor - Comedy/Romance
- 2006 Winner Critics Choice Award
- Best Acting Ensemble
Shared with: Brendan Fraser · Larenz Tate · Sandra Bullock · Ludacris · Matt Dillon · Ryan Phillippe · Terrence Howard · Thandiwe Newton · Jennifer Esposito · Shaun Toub - 2005 Nominee Critics Choice Award
- Best Acting Ensemble
Shared with: George Clooney · Matt Damon · Andy Garcia · Bernie Mac · Brad Pitt · Julia Roberts · Catherine Zeta-Jones
- 2015 Winner Christopher Award
- Feature Films
Shared with: Theodore Melfi · Peter Chernin · Jenno Topping · Fred Roos · Ivana Lombardi · Bob Weinstein · Harvey Weinstein · Dylan Sellers · G. Mac Brown
- 2021 Nominee Primetime Emmy
- Outstanding Guest Actor in a Drama Series
As Colonel James Rhodes / War Machine in New World Order (2021) - 2019 Nominee Primetime Emmy
- Outstanding Lead Actor in a Comedy Series
For playing: "Maurice "Mo" Monroe".
- 1998 Winner FFCC Award
- Best Ensemble Cast
Shared with: Heather Graham · Luis Guzmán · Philip Baker Hall · Philip Seymour Hoffman · Thomas Jane · Ricky Jay · William H. Macy · Alfred Molina · Julianne Moore · Nicole Ari Parker · John C. Reilly · Burt Reynolds · Robert Ridgely · Mark Wahlberg · Melora Walters
- 2021 Nominee Golden Globe
- Best Performance by an Actor in a Television Series - Musical or Comedy
- 2015 Nominee Golden Globe
- Best Performance by an Actor in a Television Series - Comedy or Musical
- 2014 Nominee Golden Globe
- Best Performance by an Actor in a Television Series - Comedy or Musical
- 2013 Winner Golden Globe
- Best Performance by an Actor in a Television Series - Comedy or Musical
- 2000 Nominee Golden Satellite Award
- Best Performance by an Actor in a Miniseries or a Motion Picture Made for Television
- 2007 Winner Gotham Independent Film Award
- Best Ensemble Performance
Tied with Before the Devil Knows You're Dead (2007).Shared with: Cedric The Entertainer · Chiwetel Ejiofor · Mike Epps · Vondie Curtis-Hall · Taraji P. Henson · Martin Sheen - 2005 Nominee Gotham Independent Film Award
- Best Ensemble Performance
Shared with: Sandra Bullock · Matt Dillon · Jennifer Esposito · William Fichtner · Brendan Fraser · Terrence Howard · Ludacris · Thandiwe Newton · Ryan Phillippe · Larenz Tate · Nona Gaye · Michael Peña · Shaun Toub
- 2022 Winner Grammy
- Best Spoken Word Album (Includes Poetry, Audio Books & Storytelling)
For "Carry On: Reflections For A New Generation From John Lewis" - 2017 Winner Grammy
- Best Compilation Soundtrack For Visual Media
For "Miles Ahead" artist; Miles Davis and Various Artists
- 2005 Winner Hollywood Film Award
- Ensemble of the Year
Shared with: Matt Dillon · Terrence Howard · Ludacris · Sandra Bullock · Jennifer Esposito · William Fichtner · Brendan Fraser · Thandiwe Newton · Ryan Phillippe · Larenz Tate · Shaun Toub
- 2024 Nominee Image Award
- Outstanding Supporting Actor in a Television Movie, Limited Series or Dramatic Special
- 2002 Nominee MTV Movie Award
- Best On-Screen Team
Shared with: Casey Affleck · Scott Caan · George Clooney · Matt Damon · Elliott Gould · Eddie Jemison · Bernie Mac · Brad Pitt · Shaobo Qin · Carl Reiner
- 2006 Winner Actor
- Outstanding Performance by a Cast in a Motion Picture
Shared with: Ludacris · Sandra Bullock · Matt Dillon · Jennifer Esposito · William Fichtner · Brendan Fraser · Terrence Howard · Thandiwe Newton · Ryan Phillippe · Larenz Tate · Shaun Toub
- 2007 Winner ShoWest Award
- Male Star of the Year
- 2010 Nominee Teen Choice Award
- Choice Movie: Fight
Iron Man & War Machine vs. The Hammer DronesShared with: Robert Downey Jr. - 2007 Nominee Teen Choice Award
- Choice Movie: Chemistry
Shared with: George Clooney · Casey Affleck · Scott Caan · Matt Damon · Elliott Gould · Eddie Jemison · Bernie Mac · Brad Pitt · Shaobo Qin · Carl Reiner · Eddie Izzard · Andy Garcia
- 1999 Winner OFTA Television Award
- Best Supporting Actor in a Motion Picture or Miniseries
- 2005 Winner ACCA
- Best Cast Ensemble
Shared with: Sandra Bullock · Matt Dillon · Thandiwe Newton · Ludacris · Larenz Tate · Ryan Phillippe · Terrence Howard · Shaun Toub · Jennifer Esposito · Michael Peña · Brendan Fraser · William Fichtner · Nona Gaye · Loretta Devine
- 2006 Winner Gold Derby Film Award
- Ensemble Cast
Shared with: Ludacris · Sandra Bullock · Loretta Devine · Matt Dillon · Jennifer Esposito · William Fichtner · Brendan Fraser · Terrence Howard · Thandiwe Newton · Michael Peña · Ryan Phillippe · Larenz Tate · Shaun Toub
- 2019 Nominee The BAM Award
- Best Cast
Shared with: Robert Downey Jr. · Mark Ruffalo · Chris Evans · Scarlett Johansson · Chris Hemsworth · Jeremy Renner · Paul Rudd · Benedict Cumberbatch · Chadwick Boseman · Brie Larson · Tom Holland · Karen Gilligan · Zoe Saldana · Evangeline Lilly
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