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Throughout the 1980s and 1990s, Alley appeared in various films, including Star Trek II: The Wrath of Khan (1982), Summer School (1987), Shoot to Kill (1988), Look Who's Talking (1989) and its two sequels (1990–1993), Madhouse (1990), Sibling Rivalry (1990), Village of the Damned (1995), It Takes Two (1995), Deconstructing Harry (1997), For Richer or Poorer (1997), and Drop Dead Gorgeous (1999). She won her second Emmy Award in 1994 for the television film David's Mother.

In 1997, Alley received another Emmy nomination for her work in the crime drama series The Last Don. In 2005, she played a fictionalized version of herself on Showtime's Fat Actress. She later appeared on Kirstie Alley's Big Life (2010), and was a contestant on the 12th season of Dancing with the Stars (2011–2012), finishing in second place. In 2013, Alley returned to acting with the title role on the sitcom Kirstie. In 2016, she appeared on the Fox comedy horror series Scream Queens. In 2018, she was a contestant on the 22nd series of the British reality show Celebrity Big Brother, in which she finished as runner-up.