Though Madison was not a Playmate, she posed for a nude pictorial with her other co-stars published in the November 2005 issue. She was seen as an intern working at the Playboy studios. She also worked as the designer of The Girl Next Door calendar.
In 2009, she quit her work after her split with Hefner. Madison was partnered with Dmitry Chaplin on Dancing with the Stars. In 2009, she led the Guinness World Record-breaking “largest bikini parade ever.”
Madison also starred in Peepshow, a burlesque show at Planet Hollywood. She acted as Bo Peep and Goldilocks in the show. She also appeared in films like The Last Broadcast (1998), Scary Movie 4 (2006), The House Bunny (2008), The Telling (2009), Sharknado 3: Oh Hell No! (2015).
She has also appeared in several television programs including MTV Cribs (2002), The Surreal Life (2003), The Bernie Mac Show (2004), Curb Your Enthusiasm (2005), Entourage, The Tyra Banks Show, Amazon Fishbowl, Robot Chicken, The Ellen DeGeneres Show, Phenomenon, Last call with Carson Daly, Celebrity Family Feud, Living Lohan, Dancing with the Stars, Kendra, When I was 17, etc.