2. KELLY MONACO

Hef played a big role in getting Monaco's name in the spotlight, but she's taken it from there. Monaco is the only former playmate to rise to legitimate fame with her acting talent despite using her naked body to get her foot in the door. Hef needs a lady he doesn't have to tend to, and with Kelly's Daytime Emmy nominations for General Hospital and her Dancing With The Stars trophy, we think she's clean. This relationship would be all about love, not career-catapulting business.