Cybill Shepherd kicked off her career as a model after winning the 1966 Miss Teenage Memphis beauty pageant. Fortunately director Peter Bogdanovich serendipitously picked up a copy of Glamour that happened to feature young Cybill on the cover and proceeded to cast her in his cult classic The Last Picture Show (1971), launching the aspiring actress into a long and fruitful career, as well as an affair with ol' Pete. Naturally Bogdanovich made sure that Cybill shed her threads a number of times in Picture Show, which led to several gratuitous ganders at her globes, as well as an incredible ass shot, which we're sure helped Cybill out in garnering her a Golden Globe nod for Most Promising Newcomer. With a behind like that, though, she should have won! We all became winners in early 2007, however, when Cybill guest starred as a coochie chewer on the lesbian series The L Word, popping a hint of nip while going teat-to-teat with Leisha Hailey. Looks like Cyb was doing a little Poonlighting.