NSFW November: Claudia Jennings, Miss November 1969

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.

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11 Responses to “NSFW November: Claudia Jennings, Miss November 1969”

  1. bishop2 Says:

    Claudia in the central poster: today she would be classified like “fat”…ha ha ha!!! She is so beautiful… :) Greetings from Spain!
    http://labalsadelanostromo.wordpress.com

  2. Tony Says:

    Very beautiful. I searched for November 69′, Just wanting to know who was happening, and I am not surprised to see it was someone so beautiful, with autumn leaves that fall all year long. Where is she now?

    • E. Says:

      Hi, Tony. Claudia might be my favorite of the Playmates: it is doubly sad to me that she has been dead since 1979; she was just a few months short of 30 when she died in her tragic car accident. Hard to believe. According to her wishes as expressed to family and friends, Ms. Jennings was cremated and her ashes were scattered over the ocean. But I think many fans of her large body of drive-in flicks and her memorable Playboy appearances as first PMOM and then PMOY will agree that her memory lives on.

  3. Nope Dope Says:

    Although tragic, it is unlikely that Mimi was faultless
    with regard to the accident that ended her life, just
    noting that she indulged heavily in drugs and alcohol.

    In any event, she was a sweet POA who did not
    escape the horrific jaws of the Hebrew Hollywoodland
    flesh chipping machine, largely due to her own
    sad naivety.

  4. bishop2 Says:

    I think the “Hebrew” pejorative adjective in Nope Dope’s comment is out of place here, in this clean, beautiful page… it’s as if we say “the Christian jaws destroying Iraq…” Absurd the form in both cases, without a delicate and documented explanation I can’t see in your post. In other happier order of things, greetings E. and congratulations for your page again.

  5. Ooooooya Says:

    How sad. She was lovely. It’s too bad they weren’t showing pubic hair yet at this time. I imagine her bush must have been beautiful.

  6. Michael Lee Says:

    CLAUDIA JENNINGS WAS NOT ONLY A BEAUTIFULWOMAN BUT VERY TALENTED AND OVERLOOKED. SWEETY YOU WILL ALWAYS BE IN OUR HEARTS AND MEMORIES. REST IN PEACE SWEET ANGEL AND MAY YOU WATCH OVER US. CLAUDIA YOU WILL ALWAYS BE A LEGEND AND A VERY SPECIAL PERSON. LOVE ALWAYS YOUR #1 FAN MICHAEL LEE.

  7. Curvature Aficionado Says:

    Claudia Jennings – the ultimate playmate redhead!

    Such a tragic end to her life. (One cannot help but contemplate the so-called “playmate curse”.)

    Rest in peace, adorable Claudia.

  8. Curvature Aficionado Says:

    [Addendum to my previous post.]

    Recommended viewing for Claudia fans: “The Great Texas Dynamite Chase” (1976).

    Classic 1970’s drive-in movie!

  9. Michael Lee Says:

    claudia jennings was a very beautiful woma as well as a very talented actress. claudia you are an inspiration to me and im glad to share you with people that didnt know you. we miss you and our world in entertainment isnt the same without you. heavens blessings to you sweetheart. love you always. michael lee

  10. Anonymous Says:

    Claudia was known for her strong, offensive vaginal odor. In fact, that was the main reason she was cremated.

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