Holly Madison, Bridget Marquardt, and Kendra Wilkinson in The Girls Next Door (2005)

Holly Madison and Kendra Wilkinson in The Girls Next Door (2005)

Holly Madison in The Girls Next Door (2005)

Hugh Hefner, Holly Madison, and Bridget Marquardt in The Girls Next Door (2005)

Hugh Hefner, Holly Madison, and Kendra Wilkinson in Entourage (2004)

Hugh Hefner, Holly Madison, Bridget Marquardt, and Kendra Wilkinson in The House Bunny (2008)

Hugh Hefner, Larry David, and Holly Madison in Curb Your Enthusiasm (2000)

Hugh Hefner, Holly Madison, and Kendra Wilkinson in The House Bunny (2008)

Hugh Hefner, Holly Madison, Weezer, Rivers Cuomo, Bridget Marquardt, Brian Bell, Kendra Wilkinson, Patrick Wilson, and Scott Shriner in Weezer: Beverly Hills (2005)

Holly Madison and Curtis Stone in Top Chef Masters (2009)

Holly Madison and James Oseland in Top Chef Masters (2009)

Holly Madison, James Oseland, Francis Lam, and Krista Simmons in Top Chef Masters (2009)

Holly Madison, James Oseland, Francis Lam, Curtis Stone, and Krista Simmons in Top Chef Masters (2009)

Hugh Hefner and Holly Madison in The Girls Next Door (2005)

Holly Madison in Secrets of Playboy (2022)

Hugh Hefner, Crystal Hefner, Holly Madison, Bridget Marquardt, Kendra Wilkinson, Kristina Shannon, and Karissa Shannon in The Girls Next Door (2005)

Hugh Hefner, Holly Madison, Bridget Marquardt, and Kendra Wilkinson in The Girls Next Door (2005)