History of Holly Madison in Timeline

Holly Madison is an American television personality famous for her role in the reality TV show The Girls Next Door as one of Hugh Hefner's girlfriends. Following that, she starred in her own reality series, Holly's World. Madison authored two memoirs: Down the Rabbit Hole, detailing her life in the Playboy Mansion and her relationship with Hefner, and The Vegas Diaries, which chronicles her experiences in Las Vegas.

Sections (3)

Full Timeline Early Life & Education Career & Achievements

December 23, 1979: Holly Madison's Birth

On December 23, 1979, Hollin Sue Cullen, later known as Holly Madison, was born. She would become an American television personality.

Others born on this day/year

August 2001: Madison Moves Into the Playboy Mansion

In August 2001, facing credit card debt and potential homelessness, Holly Madison moved into the Playboy Mansion and became one of Hugh Hefner's girlfriends.

2001: First Sexual Encounter with Hefner

In the summer of 2001, during her first sexual encounter with Hefner, Madison alleges that he attempted to offer her quaaludes.

February 2002: Madison Becomes Hefner's "#1 Girl"

In February 2002, after most of his girlfriends left, Holly Madison became Hugh Hefner's "#1 Girl".

November 2005: Nude Pictorial in Playboy

In November 2005, Playboy published a nude pictorial of Holly Madison with her The Girls Next Door costars in the Playboy magazine.

September 2006: Cover of Playboy

In September 2006, Holly Madison and her The Girls Next Door costars were featured again on the covers of Playboy magazine.

March 2008: Playboy Cover

In March 2008, Holly Madison and her The Girls Next Door costars were featured again on the covers of Playboy magazine.

May 2008: Hefner on Marriage

In May 2008, at the Playmate of the Year luncheon, Hugh Hefner stated that marriage was not part of his "puzzle" with Holly Madison.

October 7, 2008: Madison Announces Breakup With Hefner

On October 7, 2008, Holly Madison announced that her relationship with Hugh Hefner had ended.

February 2009: Madison quits Playboy

In February 2009, with the ending of the sixth season of the Girls Next Door Holly Madison quit working for Playboy altogether due to her split from Hefner making her position awkward.

May 2009: Guinness World Record Bikini Parade

In May 2009, Holly Madison and Las Vegas Mayor Oscar Goodman led a Guinness World Record-breaking "largest bikini parade ever".

December 6, 2009: Premiere of Holly's World

On December 6, 2009, Holly Madison's reality show, Holly's World, premiered, revolving around her life at Planet Hollywood in Las Vegas.

2009: Debut of Holly's World

In 2009, Holly Madison began starring in her own reality show, Holly's World, which ran until 2011.

2009: Madison's focus

In 2009, Holly Madison stated she was not dating again and was focused on forwarding her career.

2011: Breast Augmentation Insurance

In 2011, Holly Madison announced that she had insured her breasts for $1 million, after having undergone breast augmentation.

2011: Dating Pasquale Rotella

In 2011, Holly Madison began dating Pasquale Rotella.

2011: End of Holly's World

In 2011, Holly Madison's reality show, Holly's World, ended.

August 2012: Pregnancy Announcement

In August 2012, Holly Madison announced that she and Pasquale Rotella were expecting their first child.

March 2013: Birth of First Child

In March 2013, Holly Madison gave birth to her first child, a daughter, in Las Vegas.

September 10, 2013: Madison and Rotella's Wedding

On September 10, 2013, Holly Madison and Pasquale Rotella were married at Disneyland, with Bridget Marquardt as a bridesmaid.

2015: Publication of "Down the Rabbit Hole"

In 2015, Holly Madison released her memoir "Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny", which detailed her life in the Playboy Mansion and her recovery afterward. She stated that the environment led her to contemplate suicide.

Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny

Check it on Amazon

May 2016: Release of "The Vegas Diaries"

In May 2016, Holly Madison released her second memoir, "The Vegas Diaries: Romance, Rolling the Dice and the Road to Reinvention", which also debuted on the New York Times Best Seller list, chronicling her journey toward reinvention and self-acceptance in Las Vegas.

The Vegas Diaries: Romance, Rolling the Dice, and the Road to Reinvention

Check it on Amazon

August 2016: Birth of Second Child

In August 2016, Holly Madison gave birth to her second child, a son.

2016: Release of "The Vegas Diaries"

In 2016, Holly Madison released her second memoir, "The Vegas Diaries: Romance, Rolling the Dice, and the Road to Reinvention".

The Vegas Diaries: Romance, Rolling the Dice, and the Road to Reinvention

Check it on Amazon

September 25, 2018: Separation Announcement

On September 25, 2018, it was announced that Holly Madison and Pasquale Rotella were separated.

February 2019: Divorce Finalized

In February 2019, the divorce between Holly Madison and Pasquale Rotella was finalized.

2021: Autism Spectrum Belief and Diagnosis

In 2021, Holly Madison revealed that she believed herself to be on the autism spectrum, something her parents had long suspected, and was later formally diagnosed.

2021: Madison Shares Dark Sides of Playboy Lifestyle

In 2021, Holly Madison shared some of the dark sides of the Playboy lifestyle in an interview, which were further revealed in the 2022 Secrets of Playboy docuseries.

January 2022: Secrets of Playboy Airs

In January 2022, Holly Madison was the subject of the second episode of the A&E documentary series Secrets of Playboy. She described the Playboy Mansion as "dangerous" and "very cult-like".