The best Michael Madsen movies span several popular genres, often collaborating with directors like Oliver Stone and Quentin Tarantino. Madsen died on July 3, 2025, at the age of 67. The actor had a long career in Hollywood after getting his start as a stage actor, learning under the guidance of John Malkovich, before he got his break in Hollywood.
That break included small roles in movies like WarGames and Kill Me Again, before Quentin Tarantino made him a star by casting him in his debut film, Reservoir Dogs. After this, Madsen split his time between working on small, independent movies and films with directors like Tarantino, who used him multiple times throughout his career.
10
Free Willy (1993)
Michael Madsen Played Glen Greenwood
Free Willy
- Release Date
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July 16, 1993
- Runtime
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112 minutes
- Director
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Simon Wincer
By the time Michael Madsen appeared in the family movie Free Willy, he had already made his name working with Quentin Tarantino in Reservoir Dogs. That made his role as Glen Greenwood, Jesse’s foster dad, in Free Willy seem like a slight departure. However, Glen was the owner of an auto repair shop, which fit his reputation from previous films.
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Free Willy tells the story of a 12-year-old orphaned boy named Jesse who becomes friends with a captive orca named Willy at an amusement park. However, when he learns the park’s owner plans to “dispose” of Willy, Jesse sets out to find a scheme to break Willy out of captivity and help the whale find its freedom.
Madsen has a challenging role as a foster father to a young man who only wants to find his real mother and gets in trouble more often than most kids. However, he was instrumental in helping Jesse achieve his dreams of saving Willy, and it remains Madsen’s best feel-good movie of his career.
9
Die Another Day (2002)
Michael Madsen Played Damian Falco
Die Another Day
- Release Date
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November 22, 2002
- Runtime
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133 minutes
- Director
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Lee Tamahori
While Michael Madsen mostly starred in independent movies or films by auteur filmmakers, in 2002, he appeared in what was one of the biggest blockbusters of his career. Madsen had a role in the final Pierce Brosnan James Bond movie, Die Another Day. In this film, Madsen played Damian Falco, Jinx’s superior in the NSA.
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This film starred Brosnan as James Bond, who teamed up with NSA agent Jinx (Halle Berry) to locate a British intelligence traitor, someone connected to a North Korean operative Bond believed he had killed years earlier. Toby Stephens, Will Yun Lee, and Rosamund Pike starred as the villains in the movie.
Madsen signed on as Falco, expecting that it would be a returning role, as he and Jinx were supposed to appear in a spinoff movie that was never made. However, it was a nice payday for Madsen, and while it ended Brosnan’s run as Bond, Madsen was solid in his role.
8
The Hateful Eight (2015)
Michael Madsen Played Joe Gage
Michael Madsen appeared in several Quentin Tarantino movies, including the 2015 Western The Hateful Eight. This film follows eight strangers who seek refuge during a blizzard in a stagecoach stopover. However, some of these strangers are not who they claim to be, and almost no one gets out of this situation alive.
Michael Madsen plays a man named Joe Gage, who is also known as “Grouch” Douglass. Joe was one of the people staring at the lodge when bounty hunter Marquis Warren (Samuel L. Jackson) arrived with fellow bounty hunter John Ruth (Kurt Russell), who had a fugitive (Jennifer Jason Leigh) handcuffed to him as he brought her to justice.
Madsen’s Joe is a key part of the story’s twisting plot and delivers the exact type of performance fans would expect from him
Madsen’s Joe is a key part of the story’s twisting plot and delivers the exact type of performance fans would expect from him, reciting Tarantino dialogue. The film was not as acclaimed as other Tarantino movies, with a 74% on Rotten Tomatoes, but a Tarantino movie is still better than most films released in theaters.
7
The Doors (1991)
Michael Madsen Played Tom Baker
The Doors
- Release Date
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March 1, 1991
- Runtime
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140 minutes
- Director
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Oliver Stone
In 1991, Michael Madsen teamed with Oliver Stone for the musical biopic The Doors. This movie stars Val Kilmer as Jim Morrison, the lead singer of the classic rock band The Doors. As for Michael Madsen, he took on the role of Tom Baker, an actor from the 1960s who befriended Jim Morrison during their time in the spotlight.
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In real life, Tom Baker was one of the few people in Jim Morrison’s circle of friends, and he was able to hook up with Andy Warhol for his movie I, A Man. The role in The Doors wasn’t a huge one, but it was a familiar face working alongside Kilmer to tell the story of this iconic musician’s life.
The Doors was not a big box office success, despite Val Kilmer’s incredible performance as Jim Morrison. It also received mixed reviews, primarily due to its historical inaccuracies. However, for fans of The Doors, it offers a lot to love, and Kilmer’s performance here was easily Oscar-worthy.
6
Sin City (2005)
Michael Madsen Played Detective Bob
Sin City
7/10
- Release Date
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April 1, 2005
- Runtime
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124 minutes
Michael Madsen joined Robert Rodriguez’s adaptation of Frank Miller’s Sin City in 2005. The film was an interesting exercise for Rodriguez, who shot the movie in front of a green screen and then added a background that looked straight out of the graphic novels on which the story is based.
Sin City tells the story in six chapters, with an all-star cast taking on roles in each of the segments. Bruce Willis is the main star as Detective John Hartigan, a good cop in a city overrun with corruption. Madsen, on the other hand, is Hartigan’s partner, Detective Bob, and he betrays Hartigan to the evil Rourke family.
The betrayal was no surprise for anyone who follows Madsen’s career, but he delivered as great a performance as expected in the role of a corrupt cop on the take.
The betrayal was no surprise for anyone who follows Madsen’s career, but he delivered as great a performance as expected in the role of a corrupt cop on the take. Sin City was a box office success and received good reviews, spawning a sequel a few years later.
5
Once Upon A Time In Hollywood (2019)
Michael Madsen Played Sheriff Hackett
Michael Madsen appeared in a small role in the 2019 Quentin Tarantino movie, Once Upon a Time in Hollywood. However, his part was a very small blink-and-you-miss-it moment. He played the character of Sheriff Hackett on the fictional TV show Bounty Law. This was the show in which Rick Dalton (Leonardo DiCaprio) starred.
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This scene was shown during the dinner scene when producer Marvin Schwarz (Al Pacino) was having dinner with Rick Dalton. This was the only place in Once Upon a Time in Hollywood where he was seen. Interestingly, the scene was even longer, but it was cut down and shortened in post-production, and it still exists in the film’s deleted scenes.
4
Donnie Brasco (1997)
Michael Madsen Played Dominick “Sonny Black” Napolitano
Donnie Brasco
- Release Date
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February 28, 1997
- Runtime
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127 minutes
- Director
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Mike Newell
Michael Madsen portrayed another real-life person in the 1997 crime drama Donnie Brasco. Based on the true-crime novel by Joseph D. Pistone, the film stars Johnny Depp as Pistone, an undercover FBI agent who infiltrates the Bonanno crime family in New York City in the 1970s under the alias Donnie Brasco.
Al Pacino was Depp’s co-star, portraying Mafia hitman Lefty Ruggiero, the gangster who vouched for Donnie Brasco. As for Madsen, he stars as Sonny Black, a real-life Mafia capo named Dominick Napolitano. He is the man who mistakenly allowed Brasco to infiltrate his crew and almost inducted Donnie as a full member of the family.
Madsen received praise for his performance as the Mafia capo-turned-boss.
Donnie’s undercover work led to over 200 indictments. However, while the film didn’t show it implicitly, Sonny Black was killed for his role in allowing Donnie to get into the family. Critics loved the movie, awarding it an 88% Rotten Tomatoes score, and Madsen received praise for his performance as the Mafia capo-turned-boss.
3
Reservoir Dogs (1992)
Michael Madsen Played Mr. Blonde
Michael Madsen had starred in several movies before 1992, but it was Quentin Tarantino’s Reservoir Dogs that made him a star. Madsen was part of an impressive cast of actors who all took on assumed names, with Madsen playing Mr. Blonde, as they planned and executed a botched jewelry robbery.
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Of all the characters, it was Madsen who had the biggest chance to shine. Tim Roth was the undercover police officer who had taken a bullet in the escape, while Harvey Keitel was the secondary lead, the one man who trusted Roth’s character. However, it was Mr. Blonde who was the worst of them all, the most despicable of villains.
The scene where Mr. Blonde took a cop, tied to a chair, and then did a song and dance to “Stuck in the Middle With You” before cutting his ear off is one of the film’s most horrifying moments. Even though we don’t see the cut, it was visual enough to cause people to dismiss the movie based on violence.
2
Thelma & Louise (1991)
Michael Madsen Played Jimmy Lennox
Ridley Scott directed one of the best dramas of the 90s with Thelma & Louise. In this movie, Susan Sarandon and Geena Davis star as two friends who are taking a break from their lives for a weekend vacation. Thelma (Davis) is a housewife married to an abusive husband, while Louise (Sarandon) is a waitress dating an easygoing musician.
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When Louise shoots and kills a man who tried to rape Thelma, the two women go on the run. They realize that their lives are in danger when they become wanted for murder, and the police begin to pursue them, led by Harvey Keitel’s Det. Slocumb. Madsen plays Jimmy, Louise’s musician boyfriend.
Madsen’s role is essential because he is the person the police use to try to lure Louise back to him so that she can turn on Thelma, which she refuses to do. Thelma & Louise earned six Oscar nominations, and in 2016, the Library of Congress added it to the National Film Registry.
1
Kill Bill (2003)
Michael Madsen Played Budd
The best Michael Madsen movie was also voted one of the top 100 films of the 21st century by film professionals. This film is Kill Bill, and Madsen starred as an associate of the Deadly Viper Assassination Squad. To be more precise, he is the brother of the titular Bill, the man who ordered The Bride’s death at her wedding.
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Madsen plays Budd (also known as Sidewinder), a former member of the Deadly Vipers who works as a bouncer at a strip club. He is the third person that The Bride comes after for revenge when she wakes up from her coma. Unlike most of the Deadly Vipers, Budd actually seems to show remorse for what happened.
The first film was a monster success, making $180.9 million at the box office on a $30 million budget. It also earned Uma Thurman a Golden Globe nomination and picked up five BAFTA nominations. While Michael Madsen was only in a supporting role, he proved that he was always at his best with Quentin Tarantino.
