Cindy Crawford appeared on the cover of Playboy in 1988, and then again in 1998. Years later, she told Net-a-Porter that she had no regrets about posing nude.
Anna Faris starred in the 2008 comedy ‘The House Bunny.’ She played a Playboy Bunny who joins a sorority of awkward girls to teach them about men. Faris appeared on the cover of Playboy to promote the movie, but she kept it pretty PG.
Azealia Banks’ 2013 Playboy cover was fun and vibrant. She got a little raunchier for the rest of the photos, where she posed completely nude in a paddling pool pouring milk all over herself.
This next singer tried to spice up the magazine…..