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T.I. -

Let's start with the celebs who have a handful of arrests. The rapper has five arrests, with the first one dating back to 1998, for drug dealing.

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Connor McGregor -

The Irish MMA fighter is known for his temper, so it doesn't really come as a surprise that he was arrested five times in just two years (2018 and 2019). Twice for assault!

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Robert Downey Jr. -

The Hollywood star's troubled past is well known, and so is his criminal record. Between 1996 and 2000, the 'Iron Man' actor was arrested five times.

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Paris Hilton -

The socialite has had her troubles with the law, most notoriously for being charged with driving under the influence (DUI) and drug possession. For Hilton, it was a total of five arrests between 2006 and 2010.

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Winona Ryder -

2001 was definitely not a good year for the 'Stranger Things' actress. Winona Ryder was arrested five times during this period. Shoplifting and vandalism were among the charges.

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Mick Jagger -

We don't know if he moved like Jagger in jail, but the iconic front man of the Rolling Stones had the chance to five times. He was first arrested for public urination in 1965.

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Jane Fonda -

The veteran actress was famously arrested in 2019 for civil disobedience, after participating in a climate change protest (several more similar arrests followed). This was not, however, the first time Fonda was arrested. She has a total of six arrests on record, the first one being in 1970 on charges of drug smuggling.

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Lil' Kim -

The rapper was arrested six times. The first one  was in 1996, for possession of marijuana. She then served a one-year prison sentence in 2005 for lying in court a year earlier.

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Chris Brown -

The R&B star also has six arrests under his belt, spanning over a period of five years, between 2009 and 2014. Charges include assault and violating probation.

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Floyd Mayweather -

The boxing champ might be able to dodge many of his opponents' punches, but he wasn't able to escape the law six times. This includes two charges for battery, in 2003 and 2010, respectively.

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Lil Wayne -

The rapper enters the list with a total of seven arrests. The vast majority were for drug possession, between 2006 and 2010.

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Christian Slater -

The actor seems to get "active" every few years. Christian Slater was first arrested three times between 1989 and 1990, only to be arrested again three times in 1997. And then he was charged for sexual harassment in 2005. If you're losing track, that's seven arrests!

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Vanilla Ice -

The rapper became huge in 1990 with the hit 'Ice Ice Baby.' One year later, he was arrested for the first time. Six more arrests followed, including in 2015 when he was charged with burglary and grand theft. That's a total of seven arrests.

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Michelle Rodriguez -

The actress plays a kick*** woman in 'The Fast and the Furious' franchise. Well, maybe that's because she has some experience actually being one. Rodriguez was arrested seven times between 2002 and 2006.

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Shia LaBeouf -

The actor was first arrested in 2007 for trespassing, only to be arrested six more times leading up to 2017. Charges included being drunk in public and disorderly conduct. He's yet another celeb with seven arrests under his belt.

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50 Cent -

50 Cent was arrested eight times between 1991 and 2013, mostly related to drug possession charges.

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Amanda Bynes -

The actress ranks fairly high on this list, with a whopping eight arrests, all between 2012 and 2014, and mostly driving-related.

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Sean Penn -

The actor was a bit of a rebel in the '80s. He was even married to one of the most rebellious superstars at the time—Madonna. Penn was arrested six times in that decade, and then twice in 2009.

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Mike Tyson -

The boxing legend is no stranger to bad behavior. Tyson has in fact served time in prison. As for arrests, he has eight under his (heavyweight champion) belt.

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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 -

The singer was in the news in 2021 after being arrested on assault charges (and later for other reasons). But Manson's criminal record already had eight entries, from 1994 to 2001.

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O.J. Simpson -

O.J. Simpson's murder trial was huge in the mid '90s. But the former football player has a much longer criminal record acquired after that. He had eight charges ranging from 2001 to 2008, making for nine arrests in total.

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R. Kelly -

R. Kelly is a convicted felon and his high-profile case was on the news all over the world. In addition to the six charges he faced in 2019, the R&B singer already had another three under his belt, ever since 1998.

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Snoop Dogg -

The rapper was arrested a whopping six times for drug possession, twice for unlawful possession of a firearm, and infamously for murder in 1993.

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6ix9ine -

The rapper is also serving prison time, but he was released in 2020 and instead serves house arrest, due to his asthma and the high risk of contracting COVID-19 in prison. 6ix9ine was charged nine times in 2018 and once in 2015.

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Lindsay Lohan -

Lindsay Lohan has been famously arrested multiple times. The actress has a total of 10 charges to her name, from between 2007 and 2012.

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Courtney Love -

Courtney Love is also a member of the 10 charges club. She was first arrested in 1978 for shoplifting. Her latest charge dates back to 2005, for violating probation.

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Dennis Rodman -

The former NBA star is quite an eccentric character, and has also had problems with the law. Twelve times, to be more precise.

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Bobby Brown -

The singer and former husband of the late Whitney Houston takes the fifth spot on the list with a whopping 14 charges, ranging from 1995 to 2012.

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Suge Knight -

The former music executive and gangsta rap mogul is currently serving a 28-year prison sentence. Knight was first arrested in 1987. He amassed a total of 15 charges until 2015.

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DMX -

The late rapper will go down in history not only for his music, but also for his number of arrests: 24 in total.

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Pete Doherty -

In second place we have former Libertines front man (and Kate Moss' ex) Pete Doherty. The British rocker has 26 charges to his name, including multiple ones for drug possession.

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Martin Sheen -

And the top spot, perhaps surprisingly to many, goes to Hollywood veteran actor Martin Sheen. The race wasn't even close: he has a whopping 66 counts of civil disobedience, ever since 1986! All his arrests are tied to activism.

Sources: (TopCasinoBonus) 

See also: Stars detained or arrested protesting for a cause

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