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 (

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7 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.

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