Paris Hilton Almost Got Out of Serving Her Initial Prison Sentence, But the Judge Wasn’t Having It

Paris Hilton is one of the most high-profile celebrities of all time, a hotel chain heiress who rose to fame for her striking looks and love of partying. One of the world’s first big reality television stars, Paris Hilton has had her share of trials and tribulations.

Most notably, Paris Hilton had serious legal issues when she was in her 20s, making headlines not only for her short stint in prison but also for the crazy way that she was released early only to be sent back to jail on the judge’s orders. 

Paris Hilton smiling in front of a white background
Paris Hilton | Axelle/Bauer-Griffin/Getty Images

Paris Hilton is an heiress

Paris Hilton was born in 1981, the daughter of Rick and Kathy Hilton, and an heiress to the Hilton Hotel chain. Raised as one of four children, Paris Hilton moved frequently when she was young, exploring the world with her family and mingling with major celebrities like pop superstar Michael Jackson.

Still, Paris Hilton spent the majority of her formative years in LA, where she enjoyed spending time with her pets and her sister, Nicky Hilton. After attending several expensive schools, Paris Hilton began modeling, signing with Donald Trump’s modeling agency when she was 19.

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By the year 2000, Paris Hilton had started to attract attention from photographers and fans, many of whom raved about her unique presence and strikingly tall, thin figure.

In 2003, Paris Hilton’s star began to rise even higher when she made her reality television debut in the series The Simple Life, alongside her best friend, Nicole Richie. The show helped to cement Paris Hilton’s public persona as a “dumb blonde” with a fondness for expensive handbags, tiny dogs, and bleached blonde hair. 

Paris Hilton was known for her ‘wild child’ behavior

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Paris Hilton quickly became one of the most sought-after stars in the world — especially in the celeb-obsessed culture in LA. She was a staple presence at nightclubs and events and was often seen with other big-name stars like Lindsay Lohan and Britney Spears.

Still, by 2006, the heiress had managed to land herself in serious legal trouble. In September 2006, Paris Hilton was arrested for driving under the influence.

At the time, Paris Hilton denied that she was driving recklessly, although she did state that “maybe I was speeding a little bit.” She was sentenced to 36 months probation, but just a year later, she was caught driving on a suspended license. This time, the reality star was sentenced to 45 days in jail as recompense for breaking the terms of her probation. 

Why was Paris Hilton released and then sent back to jail?

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Paris Hilton’s legal issues were, unfortunately, only beginning when she was sentenced to 45 days in jail. She checked into jail in June 2007, but after only a few days, Hilton was released in order to serve out the remainder of her sentence in home confinement — reportedly due to a mysterious medical condition that was not disclosed to the press.

Still, the judge ended up ordering Paris Hilton back to jail after she had checked out in order to serve out the remainder of her sentence. According to a recent podcast, Paris Hilton was very upset at having to return to jail, shouting “it’s not right!” as she checked back in, and yelling for her mother.

By the end of the month, however, Paris Hilton was released from prison. Determined to have a fresh start, the heiress managed to dodge controversy and refocused her efforts on her business ventures, including fragrance launches and fashion designs. To this day, Paris Hilton remains a vital pop culture presence — although most of her original fans still remember her early days of wild partying and paparazzi scandal.