Born in Chicago, IL, Madsen was raised by his father, Cal, a fireman, and his mother, Elaine, an author, poet and Emmy-winning documentarian. Unlike his sister, Virginia Madsen, who became a popular actor after studying dancing and acting throughout her childhood, Madsen spent his youth working on cars and thinking that he would become a race car driver. Because his family relocated several times, he often found himself to be the new kid on the block, leading him to embrace his loner status early in life. He also ran afoul of the law by stealing cars and committing robbery, which led to a brief stint in prison. He eventually followed his sister into acting by way of the Steppenwolf Theatre in Chicago, where he was an apprentice for actor John Malkovich. While performing at the Steppenwolf, Madsen was spotted by acclaimed Italian director Sergio Leone, who encouraged the young actor to try a film career. Madsen heeded the advice and moved to Los Angeles in his early twenties, where he landed his feature acting debut with a few lines in the hit teen thriller, "WarGames" (1983). Following his debut, Madsen embarked on a series of small parts in a wide range of movies, including "Racing with the Moon" (1984) and "The Natural" (1984), while making his television premiere in Edward Zwick's Emmy-winning political drama, "Special Bulletin" (NBC, 1983). He quickly landed his first regular series role, playing the murderous son of a crime lord (Eli Wallach) on the short-lived series "Our Family Honor" (ABC, 1985-86). Following a small turn in the blackmail thriller "Shadows in the Storm" (1988), Madsen was a psychotic killer opposite Val Kilmer's seedy private detective in John Dahl's "Kill Me Again" (1989). Although his turn as the understanding boyfriend of Susan Sarandon in Ridley Scott's "Thelma & Louise" (1991) raised his profile substantially, Madsen had his breakout performance as psychopathic Mr. Blonde in Quentin Tarantino's own breakthrough, "Reservoir Dogs" (1992). Starring opposite heavy hitters like Harvey Keitel, Lawrence Tierney and Tim Roth, Madsen was nothing short of sensational as a recently released con who joins the crew of what turns out to be a botched diamond heist. But it was his interrogation and torture of a rookie police officer, where he slices off his ear while prancing around to the 1970s tune "Stuck in the Middle with You," that cemented his place in cinema history as playing one of the more twisted of villains.Taking a surprising turn toward family fare, Madsen played the foster father of a 12-year-old boy (Jason James Richter) who befriends a trained killer whale in "Free Willy" (1993). He went back to his sociopathic roots to play a killer hunting down his old heist partner (Alec Baldwin) in the remake of "The Getaway" (1994), which also starred Kim Basinger. Following a turn as the oldest Earp brother, Virgil, in Lawrence Kasdan's ponderous "Wyatt Earp" (1994), he hung up his holster and boot spurs to reprise his foster father role for "Free Willy 2: The Adventure Home" (1995). After playing the trained assassin hired to locate an escaped alien in "Species" (1995), Madsen portrayed the rakish member of the Hat Squad in the disappointing "Mulholland Falls" (1996). He provided able support to Al Pacino and Johnny Depp as Mafia hood Sonny Black in "Donnie Brasco" (1997) before returning to his trained assassin role for the sequel "Species II" (1998). Back on the small screen, he starred as the mysterious Mr. Chapel, a man with no first name, no past and no gun, who crafts unique punishments for criminals who have outsmarted the legal system in the short-lived drama, "Vengeance Unlimited" (ABC, 1998-99). While routinely starring in low-budget or straight-to-DVD releases like "Trail of a Serial Killer" (1998) and "Voodoo Dawn" (2000), Madsen popped up occasionally in big studio movies like "Die Another Day" (2002), playing U.S. government agent Damian Falco, who has a small, but pivotal role in redefining the relationship between James Bond (Pierce Brosnan) and his American counterparts. After a brief succession of roles in lower-grade fare, Madsen resurfaced in a high-profile way when he collaborated again with Quentin Tarantino for "Kill Bill, Vol. 1" (2003) and "Kill Bill, Vol. 2" (2004), in which he played Budd, one in a team of assassins marked for retribution by The Bride (Uma Thurman). After a welcome turn as Bruce Willis' corrupt cop partner in Robert Rodriguez's adaptation of writer-artist Frank Miller's "Sin City" (2005), he appeared in Uwe Boll's "Bloodrayne" (2006), the cinematic prequel to the popular video game, in which he was a vampire hunter schooled in battling the forces of darkness. Madsen next appeared in David Zucker's zany sequel, "Scary Movie 4" (2006), playing a crazed farmer who houses a bumbling father (Craig Bierko). Madsen returned to low-end movies following his resurgence in more mainstream Hollywood films, starring opposite Chevy Chase and Penelope Ann Miller in the farcical comedy, "Funny Money" (2007). In "Hoboken Hollow" (2007), he was an eccentric businessman who unwittingly discovers the horror behind a successful rancher (Mark Holton) and his sadistic family, while in "Vice" (2008) - which Madsen also executive produced - he was a former top cop-turned-ticking time bomb after his wife's death, who is targeted for execution by a killer following a botched drug sting. Madsen next starred in the erotic thriller, "Boarding Gate" (2008), playing the former pimp of a former prostitute (Asia Argento), who re-embark on their kinky sexual affair, which eventually becomes troubled following a botched drug deal. After a supporting turn in the made-for-television action drama "Crash & Burn" (Spike TV, 2008) and a starring role in the hostage thriller "Killing Jar" (2010), Madsen joined the cast of "24" (Fox, 2001-10) to play the recurring role of Jim Ricker, an old friend who helps Jack Bauer (Kiefer Sutherland) after the latter goes on the run.Meanwhile, Madsen - who largely remained out of the tabloid eye throughout his career - landed on the front pages of gossip websites when it became known that he was rushed to a hospital in England after a nine-day bender of booze and pills. Concerned emergency medics considered the actor a "high-risk" patient and placed him under suicide watch. Previously, he was rumored to have been in a Los Angeles-area hospital for poor mental health in 2008, a claim his representatives flatly dismissed at the time.