The Life of Barbi Benton: Hugh Hefner’s One That Got Away

Barbi Was A Playboy Cover Star Four Times

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Barbie landed her first Playboy cover in July 1969. She went on to appear on the cover three more times: March 1970, May 1972, and December 1985 (after she’d already split from Hef.) She also appeared in two nude spreads in 1973 and 1975.

“I was shy and would make the photographer turn his back when I changed poses,” she told People about her first nude shoot. “By the second one, I just let it all hang out.” Though Benton was indeed one of the Hugh Hefner’s most lasting loves, she never actually ended up becoming Playmate of the Month.