Madsen is often hired because of his deep, sexy, voice. Soon after his apprenticeship, he was cast in a small role in the movie WarGames (1983). He moved to Los Angeles and appeared in a series of minor film roles, including playing baseball player Bump Bailey in The Natural, a deranged killer in Kill Me Again (1989), and Susan Sarandon's tough but touching boyfriend "Jimmy" in Thelma & Louise (1991).
 
 He played a razor-wielding, sadistic ex-con and jewel thief, "Mr. Blonde", in the film Reservoir Dogs. The film gained attention among film critics and fans, as did Madsen's performance and the brutality of his character. During the scene in Reservoir Dogs where Michael Madsen's character, Mr. Blonde, tortures Officer Nash, actor Kirk Baltz ad-libbed a line about being father of a young child. Madsen, who himself had just become a father, was so upset by this line that he had difficulty finishing the scene. On some copies of the DVD, as Baltz completes the line, a voice can be heard off-screen saying "Oh, no, no..." The line compounded Madsen's already mixed feelings about filming the scene because of his aversion to violence in real life.
 
 Subsequently, Madsen was cast in a variety of supporting roles in major studio films, including Free Willy, Mulholland Falls, Species, and the critically-acclaimed Donnie Brasco. Quentin Tarantino wanted Madsen to play Vincent Vega in Pulp Fiction, a role that ultimately went to John Travolta (the character is the brother of Vic Vega, Madsen's character in Reservoir Dogs). However, Madsen was already committed to Wyatt Earp (1994) and couldn't appear in the film.
 
 Since his peak in the mid 1990s, Madsen has appeared in a large number of lower-budget films that have been released directly to video or television. Some notable exceptions include his major role in Quentin Tarantino's Kill Bill and appearances in the James Bond film Die Another Day and the film version of Frank Miller's Sin City. He also appeared in Scary Movie 4 in 2006 parodying Tim Robbins's character from War of the Worlds.
 
 Madsen has also appeared in a few television series, including the short-lived series Vengeance Unlimited and most recently as "Don Everest" in the poker-themed ESPN series Tilt. He appeared in Michael Jackson's 2001 music video, "You Rock My World" and has provided voice work for several video games, including Grand Theft Auto III, True Crime: Streets of L.A., and Driver 3. He also provided voice work for the movie of The Chronicles of Narnia: The Lion, the Witch and the Wardrobe as Maugrim the wolf, captain of the White Witch's secret police.
 
 Madsen's latest voice-over role is for the Playstation 2 game, Yakuza, where he voices the role of Futo Shimano, a violent and unforgiving leader of a Yakuza family.
 
 Quentin Tarantino has confimed that he will use Madsen in another upcoming movie by him, this time as the lead role of Babe Buchinsky in Inglorious Bastards. Madsen will also reprise his role as Bob in Sin City 2. He is also set to appear in House, a horror movie that is adapted from the acclaimed novel by Ted Dekker and Frank Peretti, in which he will portray a police officer. It is scheduled to be released on October 22 2007.
 
 Madsen appeared in Every Time I Die's music video "Kill The Music".