Ruehl made a big splash as a gun-toting mafia moll in Married to the Mob (1988) and received an Oscar as best supporting actress for her role in The Fisher King (1991). She won a Tony for her Broadway performance in Lost in Yonkers (1991) and appeared in the movie of the same name (1993). Her other film appearances include Radio Days (1987), Slaves of New York (1989), Last Action Hero (1993), Out of the Cold (1999), What's Cooking? (2000), and More Dogs Than Bones (2000). She had a recurring role on the sitcom Frasier as Frasier's boss (1995–96).