Ann Pennington

Janice Pennington, our Miss May 1971, seems to have a started a family tradition that Playboy photographers and fans strongly encourage. Janice walked into Playboy’s offices in 1976 with a stunning companion, her younger sister. Ann Pennington had always wanted to pose for Playboy and after seeing her sister’s centerfold, she knew she needed to make becoming a Playmate a family rite of passage. “We’re all just a little bit crazy so we have a lot of fun together,” states the all-natural blonde. Like her sister, Ann has appeared on several games shows including Truth or Consequences and The Price is Right where Janice is best-known for being the show’s longest-running Barker’s Beauty. “I never really wanted to work,” admits Ann who married her high school sweetheart when she was very young so she wouldn’t have to. Unfortunately for her, that marriage lasted only five years and our Miss March 1976 found herself wondering what she was going to do next. “I never had the drive or the desire to really do anything for work,” says the busty blonde. “I enjoy needlepoint, dancing and reading. I also go to auctions with my sister Janice to shop for antiques, because she's opening a shop in Aspen, but that’s not work.” Life for Ann changed dramatically after a ski accident on a slope in Bear Valley that caused her to rethink her life’s trajectory and discover who she truly is. “I love being a Playmate because Playboy is a great company to work for. The money's not bad either,” says our Miss March 1976. Aside from modeling for Playboy, she has also appeared in magazine ads, and has acted in movies like Funny Lady and has modeled on game shows like Card Sharks. “I realize how lucky you are to be able to do anything and, for the first time, I've been getting my head into working. I was a model for The Price is Right and also appeared in the February 1974 issue of Playboy, in a ski layout shot in Aspen.” Ann’s love life improved as quickly as her career ambitions did. During our shooting of her gatefold, our Miss March 1976 told us she wasn’t against getting married again. In fact, she would love to, but this time around, she’ll be a married, working woman. “I might try marriage again, but not for a while. The one I had was supposed to be perfect, but we just didn't grow at the same pace. Marriage is a lot of work, and I've learned that life has no guarantees,” explains Ann. “I’m not a women’s libber, but I think women have been exploited in a lot of ways. If a man and a woman are living together, I don’t think she should be the one who has to clean the toilet bowl.” In 1979, she married Shaun Cassidy, son of legendary actress Shirley Jones and half-brother of Shirley’s on-screen Partridge Family son and real-life stepson, David Cassidy. The marriage dissolved by 1992, but during that union, Ann gave birth to a daughter named Caitlin Ann. Beauty and Playboy continued to run in the family when in 2009, Caitlin Ann joined her mother and her aunt as a Playboy model. She posed for Playboy’s Playmate Feature—Playmate Daughters. We hope the Pennington women continue to keep the Playboy tradition alive and well for many generations yet to come.