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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, playing opposite John Spencer, in the beginning of WarGames, and he was also in Free Willy. 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. For Pulp Fiction, Madsen declined the role of Vincent Vega, which went to John Travolta. Madsen starred in Mike Newell's gangster film Donnie Brasco. He once said of these films: "Some of them I'm only in for 10 minutes, but they bought my name, and they bought my face to put on the DVD box with a gun. What people don't always understand is that I established a certain lifestyle for my family back in the days of Species and Mulholland Falls and The Getaway. I wasn't about to move my six kids into a trailer park. So when people offered me work, it wasn't always the best, but I had to buy groceries and I had to put gas in the car."
In Kill Bill, Madsen played assassin Budd, the brother of Bill (David Carradine). The film was released in two parts, Vol. 1 and Vol. 2. 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 described as "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.
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, where he finished in 4th place in the final.
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, he 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 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 starred in Vilan Trub's crime drama film The Dirty Kind, which is loosely inspired by Anthony Weiner.
- Lifetime Achievement Award at Red Hen Press in 2006.
- 9th Annual Malibu International Film Festival honored Madsen in April 2008 for his Achievements in the Art of Acting
- Independent Firecracker Award for his book of poetry Burning In Paradise.
- 2007 Best Actor Boston Film Festival for Strength and Honour
- 2008 Best Actor New York International Independent Film & Video Festival for Strength and Honour.
- Madsen won Ensemble of the Year for The Hateful Eight at the Hollywood Film Awards.
Vivica A. Fox, 58, reprises her Kill Bill character Copperhead 20 YEARS later in new SZA music video
Actor Michael Madsen was arrested on Wednesday night at a home in the city of Malibu, California, according to media reports.
The 64-year-old film star was allegedly arrested by Los Angeles County Sheriff’s Department deputies for allegedly trespassing on a property in the beachside area.