Although her film appearances in The Hudsucker Proxy and Naked Gun 33⅓: The Final Insult were highly publicized in 1994, little was done to further Smith's acting career. Her first starring role was as Colette Dubois, a retired spy seeking revenge for the murder of her husband, in the action/thriller To the Limit (1995). Smith next starred in the action/thriller Skyscraper (1997), which she also produced, as a helicopter pilot, Carrie Wisk, who lands on a high rise building and, upon learning it has been taken over by terrorists, becomes engaged in a deadly fight to save hostages. Both films, and Smith's performances in them, were critically panned. During the course of the litigation over her late husband's estate, her career stalled. Her legal battle, her increasing weight, and her reportedly bizarre behavior made her regular fodder for late night television comedians.

In 2002, she debuted in her own reality TV series on the E! cable network, The Anna Nicole Show. The series focused on her personal and private life in the manner of other reality shows, such as the ratings hit The Osbournes. One of the recurring guests on the show was interior designer Bobby Trendy of West Hollywood, CA, who often feuded with lawyer Howard K. Stern. The debut of the The Anna Nicole Show was the highest rated series on the network, but critics blasted it and ratings dropped with each successive week. However, it achieved a cult status among some, particularly college fraternities. The show was canceled in February 2004 due to "creative differences," but has retained some life in reruns and on DVD releases.

Smith's next appearance on the big screen was as herself in Wasabi Tuna (2003), about a group of friends who kidnap her dog, Sugar-Pie, on Halloween. She appeared as herself again in Be Cool (2005), a crime/comedy about the film and music industries that stars John Travolta, Uma Thurman and The Rock. She produced and starred as "Lucy" in Illegal Aliens, a sci-fi/comedy about beautiful space aliens saving the earth from evil. A film biography of Smith's life is now in the works. The movie will document her rise from exotic dancer to her reality show/diet spokesmodel stardom (from her late teens until her February 2007 death at age 39). Willa Ford will star as Anna in the film.

• Illegal Aliens (2007) .... Lucy
• "N.Y.U.K" (2000) TV series .... Dr. Anita Hugg
  
• "Ally McBeal" .... Myra Jacobs (1 episode, 1999)
       - Pyramids on the Nile (1999) TV episode .... Myra Jacobs
• "Veronica's Closet" .... Donna (1 episode, 1999)
       - Veronica's Wedding Bell Blues (1999) TV episode .... Donna
• Skyscraper (1996) (V) .... Carrie Wisk
• To the Limit (1995) .... Colette Dubois/Vickie Linn
• Naked Gun 33 1/3: The Final Insult (1994) .... Tanya Peters
• The Hudsucker Proxy (1994) .... Za-Za
  ... aka Hudsucker - Der große Sprung (Germany)