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Holly Madison

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Model

The Resume

    (December 23, 1979- )
    Raised in Prince of Whales Island, Alaska
    Birth name is Holly Cullen
    Acted in 'Scary Movie 4' and 'The Last Broadcast'
    Appears on 'The Girls Next Door'

Why she might be annoying:

    She dated Hugh Hefner, who was more than fifty years her senior.
    She began living in the Playboy mansion less than a week after meeting Hugh Hefner for the first time.
    Making sure her priorities were straight she dropped out of college after becoming a Playboy bunny.
    She says Hef is her soul mate, which apparently means Hef's soul didn't have a mate for 75 years until they met.

Why she might not be annoying:

    She's an animal lover and takes care of a lot of Hef's exotic pets.
    She's into classic movies and music thus the connection with her geezer boyfriend.
    She shares a room with Hugh Hefner and is his main squeeze.

Credit: Campwankyourself


Featured in the following Annoying Collections:

Year In Review:

    In 2023, Out of 59 Votes: 23.73% Annoying
    In 2022, Out of 23 Votes: 43.48% Annoying
    In 2021, Out of 59 Votes: 64.41% Annoying
    In 2020, Out of 13 Votes: 53.85% Annoying
    In 2019, Out of 10 Votes: 50.0% Annoying
    In 2018, Out of 18 Votes: 66.67% Annoying
    In 2017, Out of 21 Votes: 66.67% Annoying
    In 2016, Out of 31 Votes: 74.19% Annoying
    In 2015, Out of 8 Votes: 62.50% Annoying
    In 2014, Out of 33 Votes: 48.48% Annoying
    In 2013, Out of 116 Votes: 66.38% Annoying
    In 2012, Out of 29 Votes: 68.97% Annoying
    In 2011, Out of 83 Votes: 72.29% Annoying
    In 2010, Out of 146 Votes: 67.12% Annoying
    In 2009, Out of 97 Votes: 65.98% Annoying
    In 2008, Out of 118 Votes: 67.80% Annoying
    In 2007, Out of 304 Votes: 74.01% Annoying
    In 2006, Out of 283 Votes: 73.50% Annoying