History of Holly Madison in Timeline
"Holly Madison is an American television personality widely recognized for her past relationship with Hugh Hefner and her appearances on the reality show 'The Girls Next Door.' She further gained fame through her own reality series, 'Holly's World,' which aired from 2009 to 2011. Madison has also authored two books: 'Down the Rabbit Hole' (2015), detailing her experiences at the Playboy Mansion and her relationship with Hefner, and 'The Vegas Diaries: Romance, Rolling the Dice, and the Road to Reinvention' (2016)."
December 23, 1979: Birth of Holly Madison
Holly Madison was born on December 23, 1979, as Hollin Sue Cullen. She would later become known for her time as Hugh Hefner's girlfriend and her appearances on reality TV.
August 2001: Moving into the Playboy Mansion
In August 2001, facing financial struggles, Holly Madison moved into the Playboy Mansion and became one of Hugh Hefner's girlfriends.
2001: First Encounter with Hefner and Allegations
Holly Madison alleged that during her first sexual encounter with Hugh Hefner in the summer of 2001, he attempted to offer her Quaaludes.
February 2002: Becoming Hefner's "#1 Girl"
Following the departure of most of Hefner's other girlfriends, Holly Madison became his primary girlfriend in February 2002.
November 2005: Playboy Pictorial
Holly Madison, along with her "The Girls Next Door" co-stars, were featured in a nude pictorial in the November 2005 issue of Playboy, despite Madison never being a Playmate.
September 2006: Playboy Cover Feature
Holly Madison, Bridget Marquardt, and Kendra Wilkinson graced the cover of the September 2006 issue of Playboy.
March 2008: Another Playboy Cover Feature
The trio, including Holly Madison, were featured on the cover of the March 2008 issue of Playboy.
May 2008: Hefner Publicly Dismisses Marriage
During the Playmate of the Year luncheon in May 2008, Hugh Hefner publicly stated that while he loved Holly Madison, marriage was not in his plans.
October 7, 2008: Breakup with Hugh Hefner
Holly Madison announced her separation from Hugh Hefner on October 7, 2008, although she continued to film with "The Girls Next Door" for a while.
February 2009: Final Playboy Cover and Departure from Playboy
Holly Madison, along with her co-stars, appeared on the cover of Playboy for the last time in February 2009. Following her split from Hugh Hefner, she left her position at Playboy.
May 2009: Guinness World Record for Largest Bikini Parade
Holly Madison participated in and helped lead a record-breaking "largest bikini parade ever" in Las Vegas in May 2009. The event coincided with the 50th anniversary of the Welcome to Fabulous Las Vegas sign.
December 6, 2009: Premiere of "Holly's World"
Holly Madison's reality show, "Holly's World," premiered on December 6, 2009, offering viewers a glimpse into her life in Las Vegas.
2009: Holly's World Premiere
Holly Madison's own reality show, "Holly's World," premiered on December 6, 2009. The show focused on her life in Las Vegas and ran for two seasons.
2009: Focus on Career and Independence
In 2009, Holly Madison expressed her desire to focus on her career and her independence, stating she was happy on her own and not interested in dating.
2011: Beginning Relationship with Pasquale Rotella
Holly Madison and Pasquale Rotella began their relationship in 2011.
2011: End of "Holly's World"
Holly Madison's reality show, "Holly's World," came to an end after two seasons in 2011.
2011: Insuring Her Breasts
In 2011, Holly Madison made headlines when she insured her breasts for $1 million.
August 2012: Announcing Pregnancy
Holly Madison announced her pregnancy with Pasquale Rotella in August 2012.
March 2013: Birth of Daughter
Holly Madison welcomed her daughter with Pasquale Rotella in March 2013 in Las Vegas.
September 10, 2013: Marriage to Pasquale Rotella
Holly Madison married Pasquale Rotella, whom she started dating in 2011, at Disneyland on September 10, 2013. Bridget Marquardt served as a bridesmaid.
2015: Release of Memoir "Down the Rabbit Hole"
Holly Madison's memoir, "Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny," was published in 2015, revealing details about her life at the Playboy Mansion and her experiences afterward.
2015: Publication of "Down the Rabbit Hole"
In 2015, Holly Madison released her first memoir, "Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny." The book delved into her experiences at the Playboy Mansion and the aftermath.
May 2016: Release of Memoir "The Vegas Diaries"
Holly Madison's second book, "The Vegas Diaries: Romance, Rolling the Dice and the Road to Reinvention," was released in May 2016. It became a New York Times Best Seller and focused on her life and self-discovery in Las Vegas.
August 2016: Birth of Son
Holly Madison gave birth to her second child, a son, with Pasquale Rotella in August 2016.
2016: Publication of "The Vegas Diaries"
Holly Madison's second memoir, "The Vegas Diaries: Romance, Rolling the Dice and the Road to Reinvention," hit the shelves in May 2016. This book focused on her personal growth and experiences in Las Vegas.
September 25, 2018: Separation from Pasquale Rotella
Holly Madison and Pasquale Rotella separated on September 25, 2018.
February 2019: Divorce Finalized
Holly Madison's divorce from Pasquale Rotella was finalized in February 2019.
2021: Revealing Autism Spectrum Belief and Diagnosis
Holly Madison shared in 2021 that she believed she was on the autism spectrum. This was later confirmed with a formal diagnosis, which she discussed on the podcast "Something Was Wrong."
2021: Speaking Out and Sharing Experiences
In 2021, Holly Madison began speaking more openly about her time at the Playboy Mansion and the negative aspects of that lifestyle.
January 2022: Featured in "Secrets of Playboy"
Holly Madison was prominently featured in the second episode of the A&E docuseries "Secrets of Playboy" which aired in January 2022. She detailed her experiences and allegations against Hugh Hefner.
