Madsen was sensational in Tarantino's "Reservoir Dogs" (1992), prancing to the classic 70s tune "Stuck in the Middle with You" while slicing the ear off a bound and gagged policeman. He looked surprisingly at home throwing a football with his 12-year old foster son in "Free Willy" (1993) but took willingly to the part of Rudy, the kitten-loving sociopathic killer in the remake of "The Getaway" (1994), starring Alec Baldwin and Kim Basinger. Madsen put away his pistol for "Free Willy 2" (1995) but strapped on a holster as the oldest Earp brother in Lawrence Kasdan's ponderous "Wyatt Earp" (also 1994), played the trained assassin hired to locate an escaped alien in "Species" (1995) and 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) and reprised his role in the sequel "Species II" (1998). The actor once again tackled series TV as 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 ABC drama "Vengeance Unlimited" (1998-99).

In 2002, Madsen joined Pierce Brosnan and Halle Berry for the much anticipated James Bond feature "Die Another Day," directed by Lee Tamahori, playing CIA Agent Damian Falco, redefining Bond's relationship with his American counterparts. After a brief succession of roles in lower-grade fare, Madsen next 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) as Budd, one of the team of assassins marked for retribution by The Bride (Uma Thurman). He also had a welcome turn as Bruce Willis' corrupt cop partner Bob in Robert Rodriguez's adaptation of writer-artist Frank Miller's "Sin City" (2005). In “Bloodrayne” (2006), the cinematic prequel to the popular video game, Madsen was a vampire hunter schooled in battling the forces of darkness. Along with the other founding members of the Brimstone Society, he does battle with the evil Lord Kagan (Ben Kingsley), the most powerful man alive whose quest for even more power has no bounds. “Bloodrayne” was distributed by director Uwe Boll himself, making a paltry $1 million at the box office. Meanwhile, Madsen appeared in David Zucker’s zany sequel, “Scary Movie 4” (2004), playing a crazed farmer who houses a bumbling father (Craig Bierko) and his daughter (Conchita Campbell) during an alien invasion—a spoof of Steven Spielberg’s “War of the Wolds” (2006).