Don Cheadle’s storied acting career began in the 1980s with various television roles that led to feature film castings throughout the preceding years. Scaling the industry quickly, Cheadle was named Best Supporting Actor by the Los Angeles Film Critics for his outstanding performance alongside Denzel Washington in Devil in a Blue Dress (1995). Since then, Cheadle’s filmography has only grown wider in thematic diversity and more critically acclaimed with several Oscar-nominated performances throughout the 2000s.
Since the 2010s, Cheadle has become a household name because of his performances in multiple award-winning films and his role as James ‘Rhodey’ Rhodes aka War Machine, in Marvel Cinematic Universe films Iron Man 2 and 3, Captain America: Civil War, and Avengers: Infinity War and Endgame. He consistently delivers standout performances regardless of how small or large the role, and has blossomed into one of Hollywood’s most versatile actors. If there’s any doubt about that, check out Cheadle’s underrated, Funny-Or-Die comedy miniseries, Captain Planet on YouTube.
Next year, Cheadle is set to star in his own Disney+ series, Armor Wars, centered on “what happens when Tony Stark’s tech falls into the wrong hands.” Cheadle is also slated for Marvel’s Secret Invasion premiering in 2023. Before watching those shows, check out Don Cheadle’s best movies, ranked.
9 Out of Sight (1998)
Universal Pictures
Steven Soderbergh’s heist film Out of Sight casts frequent collaborator (Cheadle) in a rare villain role. Appearing alongside George Clooney and Jennifer Lopez, Cheadle shines as both antagonist and comedic relief. Though Cheadle has more memeroable performances, Entertainment Weekly voted it as the sexiest film ever on their “50 Sexiest Movies Ever” poll due to the romance between Clooney and Lopez. The film also secured Academy Awards nominations for Best Adapted Screenplay and Best Film Editing, making it a worthy entry to Cheadle’s filmography.
8 Captain America: Civil War (2016)
Walt Disney Studios Motion Pictures
The final entry in Captain America’s MCU trilogy is widely lauded as the 5th Avengers film for its huge ensemble cast and MCU-altering plot. After Age of Ultron, the Avengers public and governmental reputation are in question, leading to the Sokovia Accords–an initiative to restrict the Avengers and other “enhanced individuals” to prevent further superpower related disasters.
The Accords pit Avengers against each other in 2 groups, one led by Iron Man and the other led by Captain America — that’s where Don Cheadle’s War Machine comes in. A loyal ally to Tony Stark, Rhodey, nearly becomes a martyr to the cause, but is instead left paralyzed after being shot out of the sky in an intense battle with Vision. This is a pivotal moment in the film that solidifies the division between the Avengers; Cheadle’s performance is a highlight of Captain America: Civil War and perhaps his best since the Iron Man franchise.
7 Hamburger Hill (1987)
Paramount Pictures
Starring in large-ensemble war films seems like a rite of passage for young actors hoping to break into Hollywood’s most exclusive roles. In one of his early roles, Cheadle plays a soldier fighting in one of the most violent battles in the Vietnam War. Hamburger Hill is a realistic gruesome, tragic, disastrous depiction of war that makes for an empowering message against it. As the only Black soldier in the group, Cheadle’s character represents a large sect of Black men who fought valiantly in Vietnam for a country that really didn’t treat them with the respect and honor they deserved at home.
6 Avengers: Infinity War (2018)
Avengers: Infinity War features the disbanded Avengers against their most harrowing opponent, Thanos. Despite losing the most from the conflicts in Civil War, War Machine is actually the person who put aside the group’s differences and broke the Sokovia Accords, allowing the Avengers in hiding to join the fight against Thanos.
Infinity War largely focuses on Thanos’ conquest and motivations for pursuing the Infinity Stones; however, it’s also the film that many key MCU characters meet each other for the first time. Without concrete performances from seasoned actors like Don Cheadle, tying characters together and bridging storylines becomes much more difficult.
5 Boogie Nights (1997)
New Line Cinema
Boogie Nights has an extremely recognizable and memorable cast that features many actors who are still relevant today. Paul Thomas Anderson’s script on the Golden Age of Porn was an unlikely success due to its wild subject matter; however, it has maintained critical acclaim and cult-classic status among casual moviegoers enthralled by its award-winning cast, writing, and soundtrack.
Don Cheadle’s character, Buck Swope, may be easily overlooked among this stellar ensemble; however, his performance and characterization of a Black man struggling with his identity has been praised, especially considering the many less nuanced depictions of Black culture and masculinity throughout this time period.
4 Avengers: Endgame (2019)
The followup to Avengers: Infinity War, Endgame is an action-packed, emotional, epic that concludes storylines sprawling 22 films. The film follows the remaining Avengers five years after their defeat at the hands of Thanos, and their attempt to reverse the consequences of Thanos’ “snap.” War Machine is integral in accomplishing the “time heist,” bringing the fallen Avengers back to the final fight against Thanos. The film obviously had major repercussions for every character in the MCU and the next time we’ll see Cheadle’s War Machine is the Disney+ series, Armor Wars.
3 Fail Safe (2000)
Warner Bros. Television
Fail Safe is a live television broadcasted play that was adapted from a 1964 film of the same name and a Cold War novel by Eugene Burdick and Harvey Wheeler. While the film’s style may be unconventional — it’s black and white photography even a bit deceiving — the film is surely ahead of its time and a poignant reminder of the frail line that is civility. Don Cheadle bolsters a cast featuring George Clooney, Sam Elliot, Harvey Keitel, and James Cromwell.
2 Hotel Rwanda (2004)
MGM Distribution
There’s no film on this list more important to Don Cheadle’s legacy than 2004’s Hotel Rwanda. As the lead, Cheadle secured a Best Actor Oscar nomination while highlighting a real-life humanitarian crisis, the Rwandan Genocide in 1994. Cheadle plays a hotel manager who courageously chooses to save thousands of refugees by hiding them in his hotel. For its cultural importance alone, Hotel Rwanda is an essential watch; but Cheadle’s performance makes it all the more captivating.
1 Crash (2004)
Lions Gate Films
Paul Haggis’ story about racism, economic inequality, and power dynamics won the Academy Award for Best Picture in 2006. Although it’s since been hailed as one of the worst Best Picture Oscar winners of the 2000s, it’s still a great film with standout performances from Don Cheadle, Matt Dillon, Thandiwe Newton, and Terrence Howard. Crash confronts critical issues head-on and forces audiences to realize the interconnected nature in which humans think, work, and feel beyond race, financial situation, or social status.
