She also once had a red Playboy Bunny logo tattooed on her lower back but later had it removed.
In 2003, Madison was the subject of a Playboy Cyber Girl of the Week pictorial on the magazine's website.
In 2009, Madison attempted a Guinness World Record rallying women from all over Las Vegas to hold the World's "largest bikini parade ever," winning the title.
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She was named among the top Hooters girls of all time in 2008 as part of the restaurant's twenty-fifth anniversary.
Madison has spoken openly about her cosmetic surgeries, having had both a rhinoplasty and breast augmentation.
During an interview at the Playmate of the Year luncheon in May 2008, Hefner stated, "I love Holly very much and I think we’re going to be together the rest of my life, but marriage isn’t part of my puzzle.
It’s not a personal thing; I just haven’t had much luck with marriages." On October 7, 2008, Madison announced in a video posted on that her relationship with Hefner had ended, but that she, Bridget Marquardt, and Kendra Wilkinson are "still filming stuff together".
In the Season 3 episode "Girls Next Door," Madison stated that she wanted to have a career producing Playboy spreads.
During seasons three and four, Madison was shown working at the Playboy studios as an intern and later a junior photo editor.Madison was likewise initially signed to a three month contract, but she has since extended her contract to a full year.Like former The Girls Next Door co-star, Kendra Wilkinson, Madison stars in her own reality show, Holly's World, which revolves around her life at Planet Hollywood in Las Vegas.In April 2007, Madison was featured nude in a PETA advertisement, with the tagline "I'd Rather Go Naked Than Wear Fur".In February 2009, she quit working for the company altogether due to the split from Hefner making her position "awkward".She also appeared on the cover and inside of the November 2005 issue of Playboy, along with Marquardt and Wilkinson, as part of a special pictorial promoting The Girls Next Door.