2. Stacey Dash
The former teen actress, star of Clueless, cousin of Damon Dash and mother of two made a serious claim for Hollywood’s hottest MILF with her pictorials for Playboy and Smooth at 40 and 44, respectively.
Stacey Lauretta Dash is an American actress and former talk show host. Dash is known for her co–starring role as Dionne Marie Davenport in the 1995 feature film Clueless and its eponymous television series. She has also appeared in films such as Moving, Mo’ Money, Renaissance Man and View from the Top.
Other television work by Dash includes appearances in series such as CSI: Crime Scene Investigation, Single Ladies and the reality TV show Celebrity Circus. She has also appeared in music videos for Carl Thomas’ “Emotional” and Kanye West’s “All Falls Down”.