The lovely and talented Claudia Jennings was Playboy‘s Miss November 1969, and Playmate of the Year in 1970. Her birth name was Mary Eileen Chesterton. If it was me, I’d’ve changed my name too — but I would have just switched my first name to Chesty. Can you dig it? “Hi, I’m Chesty. Chesty Chesterton.” That is a name you can take straight to the mother effing bank!
Photographed by Pompeo Posar
Her father was a sales manager and her mother was a college professor. She was raised in Milwaukee, Wisconsin, and later moved to Evanston, Illinois, where she graduated from high school in 1968. Later that year, she joined the Hull House theater company in Chicago and got a job as a receptionist at the offices of Playboy magazine (the wiki).
Claudia feels it’s necessary for her, at this point in her career, to move to one coast or the other, for the Windy City’s theatrical opportunities are limited. “Every actress has her particular skills and drawbacks,” says Claudia. “It’s a show-business axiom that if you really want to overcome your limitations, you go to New York, but if you’re satisfied with your skills, then you’re ready for Hollywood. The reasoning is that with a stage play, you get to work with the same material over a longer period of time than you do with a film, so you have more of a chance to improve.” (“Acting Playmate,” Playboy, November 1969.)
Five years later she was unemployed, single, and depressed; ten years later, she was dead. If you ask me, she chose the wrong coast. I think her sadly short life took a left turn at Albuquerque when she left Chicago and went to that shithole Los Angeles. In Hollywood, she appeared on an episode of The Brady Bunch in 1973 and lived with songwriter Bobby Hart (actual birth name Robert Luke Harshman; do you suppose they called each other by their real names when they were at home, or went with the show biz handles? oh, I fervently hope he called her Chesty…) from 1970-1975. He was the less handsome half of the almost-kinda-famous songwriting duo Boyce and Hart.
I assume the boyfriend got her the part on The Brady Bunch because the Monkees and the Brady Bunch appeared in each other’s shit a lot and Boyce and Hart wrote (and sometimes performed) most of the tunes for the Monkees — please tell me it is not news to you that the Monkees were a sham act developed to be a sort of made-for-tv-Beatles — including “Last Train to Clarksville” and the show’s theme (“Hey, hey, we’re the Monkees,” etc). They also penned such hits as “I’m Not Your Stepping Stone” and “Come a Little Bit Closer.” Hart broke up with her in ’75 and, living alone in much smaller quarters than she had been accustomed to, she got super-depressed, turned to a party crowd, and started regularly doing heroin and coke.
On the career side, throughout the 70’s, Claudia appeared in films, mainly just drive-in horror movie flicks. The wiki claimed they called her Queen of the B’s but I’m a huge B-movie guy and I have never heard this. I mean, I recognized her, but I didn’t think of her particularly as the queen. And the wiki has it somewhat wrong: I wouldn’t really call them B movies, because I associate that with an earlier genre of film, a la Ed Wood.
The types of 1970’s movies that Claudia was in are more like cult classics, thinly veiled excuses for weirdo softcore porn. Think of it as early skinemax, or very lite spatterporn. Personal favorites are Unholy Rollers about the motherfucking all-girl ROLLER DERBY (sorry, I get excited, cause, you know … sk8 or die), Deathsport, which takes place in the year 3000, and Gator Bait, which I believe needs no explanation.
In ’79, she auditioned to replace Kate Jackson on Charlie’s Angels but good old Aaron Spelling and company were not fans of her Playboy credit and gave the job to Shelley Hack instead. (Hack’s turn as Tiffany Welles almost sank the show and she was fired in 1980 anyways, so whatever.)
On October 3, 1979, almost a decade to the day after her Playboy pictorial hit the newsstands, Claudia was driving to the home of her on-again, off-again boyfriend Stan Herman in Malibu to pick up her shit cause they had broken up again when her Volkswagen Beetle was hit by a van and she was killed. She was thirty years old.
The Thought Experiment 