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T.I. -

We begin with celebrities who have several arrests. The rapper had the first incident in 1998, related to drug dealing.

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Connor McGregor -

The UFC legend Conor McGregor, known for his explosive personality, has faced multiple arrests, including incidents involving property damage and violent behavior. One notable arrest followed an incident in 2018 when McGregor attacked a UFC bus, resulting in injuries to other athletes.

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Winona Ryder -

In 2001, the actress from 'Stranger Things' had a challenging year. Winona Ryder faced five arrests during this time, with charges including shoplifting and vandalism.

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Mick Jagger -

It is unclear whether he danced like Jagger while incarcerated, but the legendary lead singer of the Rolling Stones had the opportunity to do so on five occasions. His initial arrest for urinating in public occurred in 1965.

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Lil' Kim -

The rapper has been arrested on six occasions. In 1996, she was arrested for possessing marijuana. Later in 2005, she was sentenced to one year in prison for perjury committed a year prior.

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Chris Brown -

The R&B singer has been arrested six times from 2009 to 2014, facing charges that involve assault and probation violation.

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Floyd Mayweather -

The boxing champion successfully avoided many punches from his opponents, but he faced legal consequences in six instances. These included two battery charges, one in 2003 and another in 2010.

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Lil Wayne -

The rapper is included in the list for having been arrested seven times, mainly for drug possession, from 2006 to 2010.

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Christian Slater -

Christian Slater has had a pattern of periodic activity, particularly in legal matters. Between 1989 and 1990, he faced arrest on three occasions, and in 1997, he was arrested another three times. Furthermore, in 2005 he was charged with sexual harassment, amounting to a total of seven arrests.

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Vanilla Ice -

In 1990, the rapper gained immense popularity with the widely successful track 'Ice Ice Baby.' In the subsequent year, he faced his initial arrest. Over the following years, he encountered six more arrests, with the most recent one occurring in 2015, wherein he was charged with burglary and grand theft. Consequently, his total number of arrests reached seven.

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Michelle Rodriguez -

The actress portrays a strong female character in 'The Fast and the Furious' film series. Perhaps this is due to her personal experience, as Rodriguez was arrested a total of seven times from 2002 to 2006.

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Shia LaBeouf -

The actor's initial arrest occurred in 2007 due to trespassing, followed by an additional six arrests leading up to 2017. Charges consisted of being drunk in public and engaging in disorderly conduct. He joins the ranks of numerous celebrities with seven arrests.

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50 Cent -

50 Cent was taken into custody on eight different occasions, from 1991 to 2013, primarily for drug possession offenses.

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Amanda Bynes -

The actress is quite high on this list, with a surprising eight arrests, taking place from 2012 to 2014, mainly related to driving.

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Sean Penn -

During the 1980s, the actor displayed a rebellious nature and formed a marital bond with the iconoclastic superstar, Madonna. Penn faced six arrests in that era and subsequently encountered legal trouble twice in 2009.

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Mike Tyson -

The famous boxer is familiar with misconduct. Tyson has, in fact, been incarcerated. When it comes to arrests, he has accumulated a total of eight throughout his career.

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Justin Bieber -

Can you believe the Canadian singer has been arrested the exact same amount of times as Mike Tyson? Assault, DUI, and reckless driving make up most of the charges.

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Marilyn Manson -

In 2021, the singer garnered media attention for his arrest on assault charges, adding to his pre-existing criminal record of eight incidents between 1994 and 2001. He also faces a series of rape allegations in recent years, which he denies.

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O.J. Simpson -

O.J. Simpson's murder trial garnered immense attention during the mid '90s. However, his criminal history extends well beyond that period. Between 2001 and 2008, he faced eight charges, resulting in a total of nine arrests.

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R. Kelly -

R. Kelly, a well-known celebrity, was widely covered in the media due to his criminal record. Apart from the six accusations he faced in 2019, the famous R&B artist had previously encountered three charges dating back to 1998.

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Jane Fonda -

The well-known actress was famously apprehended in 2019 for defying civil rules, subsequent to her involvement in a demonstration against climate change (more arrests of a similar nature ensued later on). Nonetheless, this was not Fonda's initial encounter with detainment. A total of six arrests have been documented, with the earliest occurring in 1970 for allegedly engaging in drug trafficking.

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Snoop Dogg -

The rapper was arrested a staggering six times for drug possession, twice for illegal possession of a firearm, and famously for murder in 1993, but was ultimately acquitted.

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Paris Hilton -

Hilton, a socialite, has faced legal issues, notably being charged with DUI and drug possession. She had a total of five arrests from 2006 to 2010

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6ix9ine -

The rapper, 6ix9ine, was released from prison in 2020 and is currently under house arrest due to his asthma and the increased risk of COVID-19 in correctional facilities. He faced charges nine times in 2018 and once in 2015.

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Dennis Rodman -

The former NBA star is known for being an eccentric individual and has encountered legal issues on exactly twelve occasions.

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Robert Downey Jr. -

The past difficulties of the Hollywood actor are widely recognized, as is his record of illegal activities. From 1996 to 2000, the actor known as 'Iron Man' was arrested on five occasions.

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Bobby Brown -

Bobby Brown, the singer and ex-husband of the late Whitney Houston, secures the fifth position on the list with an astonishing 14 charges spanning from 1995 to 2012.

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Suge Knight -

The ex-music executive and gangsta rap leader is presently incarcerated for a period of 28 years. Knight was initially apprehended in 1987 and faced a cumulative of 15 charges until 2015.

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Courtney Love -

Courtney Love is part of the 10 charges club as well. Beginning in 1978, she was arrested for shoplifting, with her most recent charge occurring in 2005 due to probation violation.

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DMX -

The rapper, who has passed away, will be remembered for both his music and the significant number of arrests he had, totaling 24.

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Lindsay Lohan -

Lindsay Lohan, the well-known actress, has gained attention for her frequent arrests, accumulating a total of 10 charges between 2007 and 2012.

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Pete Doherty -

Coming in second is Pete Doherty, former frontman of the Libertines and ex-partner of Kate Moss. This British musician faces a total of 26 charges, with several related to the possession of illegal substances.

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Martin Sheen -

Surprisingly, the Hollywood actor Martin Sheen has claimed the top spot with an impressive 66 counts of civil disobedience since 1986, according to sources. All of his arrests are related to activism.

See also: Stars detained or arrested protesting for a cause

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