Madsen’s career spans 25 years and close to 300 credits playing memorable characters in a myriad box office hits, including Robert Rodriguez and Frank Millers’ Sin City (2005), Pierce Brosnan’s final James Bond film, Die Another Day (2002), alongside Al Pacino and Johnny Depp in Donnie Brasco (1997), the sci-fi horror Species (1995), the family drama Free Willy (1993), and Ridley Scott’s much lauded Thelma & Louise (1991). Other notable films include War Games (1984), The Killing Time (1987), The Doors (1991), Wyatt Earp (1994), BloodRayne (2005), Scary Movie 4 (2006), Hell Ride (2008), and Vice (2008).
Madsen has received Best Actor awards for his role in the Irish boxing film Strength and Honour (2007) from the New York International Film Festival, the Boston Film Festival and the Downtown Los Angeles Film Festival.
In addition, Madsen is an accomplished poet, with his first book, Burning In Paradise, winning the Independent Firecracker Award, and the international bestseller The Complete Poetic Works. His poetry has an international following that has been honored at International Poetry Festivals in Genoa, Italy and Mexico. He was recently the Guest of Honor at the Crossing Border Festival in Netherlands. In 2009, he released American Badass, which was dedicated to the memory of the late David Carradine, his friend and Kill Bill co-star.
In 2014, Madsen appeared in the Iggy Azalea/Rita Ora music video for their song Black Widow, which is an homage to Kill Bill and has been viewed over 545 million times on YouTube.