Madsen began working at the
Steppenwolf Theatre Company in Chicago, where he served as an apprentice under
John Malkovich and appeared in a production of
Of Mice and Men. His first notable film role was a small part for the science fiction film,
WarGames. He appeared in
John Dahl's thriller
Kill Me Again as criminal Vince Miller opposite
Val Kilmer and
Joanne Whalley. In
Quentin Tarantino's directorial debut film
Reservoir Dogs, Madsen played "Mr. Blonde", a cruel criminal.
Steve Buscemi received the role of "Mr. Pink", which Madsen wanted because it had more scenes with
Harvey Keitel. In 2004, Tarantino discussed an idea for the film to unite Madsen and Travolta, as The Vega Brothers. In 2007, Tarantino said the film (which he intended to call
Double V Vega) was "kind of unlikely now", because of the age of the actors and the onscreen deaths of both characters. Madsen appeared in
Uwe Boll's
BloodRayne, a film he said is "an abomination... It's a horrifying and preposterous movie." He won Best Actor awards at the
Boston Film Festival and New York International Independent Film and Video Festival for his performance in
Strength and Honour. He played himself in the
mockumentary Being Michael Madsen. Madsen co-starred in
Coma, a Web series on
Crackle. All Star Festival Parade (with his son, right) He played
Jim Ricker, the old friend of
Jack Bauer (
Kiefer Sutherland), in the
eighth season of
24. Madsen starred in the comedy film
Let the Game Begin. On January 5, 2012, he entered the
Celebrity Big Brother house and he finished in 4th place in the competition. In February 2014, he played
Las Vegas casino mogul
Ted Binion in
Josh Evans' film
Death in the Desert. The screenplay was written by
John Steppling, based on the book
Death in the Desert by crime writer
Cathy Scott.In August 2014, Madsen starred in the
Kill Bill-themed music video for the song "
Black Widow" by
Iggy Azalea featuring
Rita Ora. Madsen starred in the ensemble western film
The Hateful Eight. He was among a number of people rumored to have leaked the film's script before it was released, causing Tarantino to almost not make the film and eventually rewrite it. It was later revealed that Madsen was not responsible for leaking the script. In 2016, he played a dramatized role of former
Texas Ranger Phil Ryan in
Real Detective on the
Investigation Discovery network. He was an executive producer in Vilan Trub's crime drama film
The Dirty Kind, which is loosely inspired by
Anthony Weiner. In 2024, he played Kensei, a "white Samurai" operating an underground society in the thriller Dark feathers: Dance of the Geisha, directed by Crystal J. Huang and Nicholas Ryan. His performance in this thriller earned him the Best Supporting Actor award at the 2024 Hollywood Reel Independent Film Festival. ==Personal life==