From Lindsay Lohan's SIX bookings to Robert Downey Jr's legendary police portrait – as Justin Timberlake's red-eyed mugshot goes viral following his DWI arrest – where does it rank among Hollywood's most iconic jail snaps?

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Justin Timberlake‘s mugshot sent social media into a frenzy on Tuesday, after it was revealed that the singer had been arrested for driving while intoxicated.

The hitmaker was pictured in handcuffs after being charged with the offence, with police saying he ran a stop sign and veered out of his lane in the posh seaside summer retreat.

Obtained by DailyMail.com, Justin’s mugshot showed the singer staring stony-faced into the camera moments after he was pulled over, and it has already sparked a flurry of viral memes and social media reaction.

Of course Justin is far from the first big-named star to face the indignity of a mugshot, with names such as Lindsay Lohan, Robert Downey Jr and Justin Bieber enduring the photoshoot no Hollywood star wants to sign up.

But where does Justin’s mugshot rank among some of the most iconic in Hollywood history? MailOnline takes a look-back at some of the most legendary mug shots…

Justin Timberlake 's mugshot sent social media into a frenzy on Tuesday, after it was revealed that the singer had been arrested for driving while intoxicated

Justin Timberlake ‘s mugshot sent social media into a frenzy on Tuesday, after it was revealed that the singer had been arrested for driving while intoxicated

Robert Downey Jr

He is far from the latest star to suffer a brush with the law, with Robert Downey Jnr's 1999 mugshot (pictured) one of the most famous in Hollywood history

He is far from the latest star to suffer a brush with the law, with Robert Downey Jnr’s 1999 mugshot (pictured) one of the most famous in Hollywood history

Despite now being one of the biggest earning stars in Hollywood history, thanks to his role in Iron Man, Robert Downey Jr endured a tough few years in the industry when he battled drugs and alcohol addiction.

From 1996 to 2001, the Oscar winner was arrested several times, with the first being for possession of heroin, cocaine and a .357 Magnum handgun – this one unloaded – while roaring down Hollywood’s Sunset Boulevard. 

In 1997, after missing repeated drugs tests, he was given a 180-day jail sentence for violating probation but was caught fighting with another inmate. 

Fellow prisoners reportedly targeted the celebrity in their midst and Downey Jr twice woke up in a pool of his own blood.

‘I would never tell you the worst things that have happened to me,’ he once said of his time behind bars.

The actor spent another year incarcerated, this time undergoing drug treatment, in 1999, with his now-iconic smiling mugshot taken while he was bring transferred to the California Substance Abuse Treatment Facility and State Prison.

But after Robert met his wife Susan in 2003, he vowed to give up drugs for good, and after landing his starring role in Iron Man, he became one of the highest-paid actors in Hollywood history.

Lindsay Lohan

Lindsay Lohan has endured multiple unwanted jail photoshoots, including a DUI arrest in 2007 (top left), stealing a necklace (bottom centre) and assaulting a woman in a nightclub

Lindsay Lohan has endured multiple unwanted jail photoshoots, including a DUI arrest in 2007 (top left), stealing a necklace (bottom centre) and assaulting a woman in a nightclub

After emerging as a child star, Lindsay has endured multiple brushes with the law, resulting in a collection of mugshots that no star would wish to have.

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In May 2007, she was arrested for driving under the influence of alcohol (DUI), and despite undergoing a 45-day treatment programme, she was arrested again just weeks later for felony possession of cocaine, and driving with a suspended license.

In May 2010, while she was travelling to promote a film at the Cannes Film Festival, Lindsay missed a court date, and a bench warrant was issued for her arrest, before she posted bail.

In 2011, she was then arrested yet again for the theft of a necklace from a jewellery shop, and the following year she was placed in a jail cell for the fifth time, under suspicion of fleeing the scene of an accident. 

Lindsay’s sixth – and hopefully final – mugshot came in November 2012, when Lindsay was arrested for allegedly assaulting a woman in a New York nightclub, however she was not prosecuted.

Khloe Kardashian

Khloe Kardashian was arrested for driving under the influence in 2007, with her post-arrest image showing her heavily made-up complexion despite her brush with the law

Khloe Kardashian was arrested for driving under the influence in 2007, with her post-arrest image showing her heavily made-up complexion despite her brush with the law

Many fans of the legendary Kardashian family may struggle to remember times before their reality show dominated the US landscape, and that may prove to be a good thing, given Khloe’s famous arrest – and subsequent mugshot in 2007.

Khloe was arrested for driving under the influence in 2007, with her post-arrest image showing her heavily made-up complexion despite her brush with the law.

While she was originally sentenced to community service, and required to complete an alcohol treatment programme, the star was then sentenced to 30 days in jail for failing to meet the judge’s requirements. She served just three hours.

Khloe’s arrest did feature prominently on the third season of Keeping Up With The Kardashians, with the nonplussed reality star saying: ‘I really wasn’t that drunk. It wasn’t a high percentage. My judge is not very happy with me.

‘He thinks that my job is a luxury and that there’s no excuse on why I got kicked out [of the treatment programme].’

Justin Bieber

Justin Bieber posed for his famous smiling mugshot when he was just 19, after being arrested under suspicion of driving under the influence

Justin Bieber posed for his famous smiling mugshot when he was just 19, after being arrested under suspicion of driving under the influence

As one of the planet’s most well-known child stars, it was no surprise that Justin’s career took a dramatic turn as he reached adulthood, with the heartthrob arrested in 2014 under suspicion of driving under the influence. 

The police report held that Justin had been drag racing, and that when the officer stopped him, the pop star’s breath smelled of alcohol and his eyes were bloodshot. 

After being arrested the star’s had his mugshot taken, and his confident smile was beamed worldwide when news of his legal troubles broke.

Later that day, Justin’s $2,500 bail was posted and the Baby singer got released from prison.

The plea bargain he got that August required 12 hours in anger management lessons and $50,000 forked over to charity, among other provisos, but he evaded a prison sentence after pleading guilty to resisting arrest and careless driving.

Mick Jagger

One of Hollywood's earliest celebrity mugshots came from one of rock's first legends, with Mick Jagger arrested in Sussex in 1967 for Amphetamine possession

One of Hollywood’s earliest celebrity mugshots came from one of rock’s first legends, with Mick Jagger arrested in Sussex in 1967 for Amphetamine possession

One of Hollywood’s earliest celebrity mugshots came from one of rock’s first legends, with Mick Jagger arrested in Sussex in 1967 for Amphetamine possession.

At the time the Rolling Stones hitmaker was with bandmate Keith Richards who was allowing guests to smoke cannabis in his home.

Mick’s black and white dapper mugshot is a far cry from the snazzy looks the star regularly sports on stage.

He and Keith was both convicted and sentenced to time in prison – three months and one year respectively – however they appealed their sentences and they were overturned. 

Paris Hilton

Paris Hiton's own brushes are law aren't far from competing with her former pal Lindsay Lohan, with a pair of viral mugshots to her name

Paris Hiton’s own brushes are law aren’t far from competing with her former pal Lindsay Lohan, with a pair of viral mugshots to her name

Paris Hilton’s own brushes with the law aren’t far from competing with her former pal Lindsay Lohan, with a pair of viral mugshots to her name.

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The heiress was first arrested in 2006 when she was found driving under the influence, suspending her license, and she was pulled over multiple times for continuing to drive with an invalid license.

In 2010, Paris was arrested after being found in a car with her boyfriend Cy Waits, and after seeing marijuana smoke wafting from the car, she was charged for possession of marijuana and cocaine, leading to her second mugshot.

The star pled guilty to drug possession and obstructing an officer, and was sentenced to a year’s probation, a fine and community service. 

Paris did eventually serve time behind bars in 2007 for a probation violation, but was released after 23 days for good behavior.

Shia Lebeouf 

In 2007, Shia Lebeouf was arrested in Chicago, Illinois for misdemeanor trespassing, leading to a smiling mugshot being taken

In 2007, Shia Lebeouf was arrested in Chicago, Illinois for misdemeanor trespassing, leading to a smiling mugshot being taken

In recent years Shia has regularly made headlines thanks to his troubled behaviour, with the star himself claiming he’s been incarcerated five times, with his first being for shoplifting at the age of nine.

In 2007, the Transformers star was arrested in Chicago, Illinois for misdemeanor trespassing, leading to a smiling mugshot being taken.

The star allegedly visited a Walgreens many times in one night while intoxicated and refused to leave after several requests by security. Charges against him were later dropped.

Keanu Reeves

Before becoming one of Hollywood's biggest names, thanks to John Wick and The Matrix, Keanu Reeves was arrested in 1993 for driving under the influence and reckless driving

Before becoming one of Hollywood’s biggest names, thanks to John Wick and The Matrix, Keanu Reeves was arrested in 1993 for driving under the influence and reckless driving

Before becoming one of Hollywood’s biggest names, thanks to John Wick and The Matrix, Keanu Reeves was arrested in 1993 for driving under the influence and reckless driving.

The then-fresh faced star’s mugshot features his luscious raven locks on full display, though little is known about the details of his brush with the law.

Keanu reportedly admitted to driving under the influence, and was not charged.

Nick Nolte

Actor Nick was famously arrested in Malibu in 2002 for DUI and a drug charge, and posed for a wild-haired mugshot in a colourful floral shirt

Actor Nick was famously arrested in Malibu in 2002 for DUI and a drug charge, and posed for a wild-haired mugshot in a colourful floral shirt

Actor Nick was famously arrested in Malibu in 2002 for DUI and a drug charge for being under the influence of the drug gamma-hydroxybutyrate, commonly known as GHB. 

The star’s wild-haired mugshot, where he sported a colourful Hawaiian shirt, is one of the must famous in Hollywood history.

He later wrote in his memoir: ‘It went viral — my hair wild, my expression unsettling, looking like an asylum inmate out for a lark. 

In 1992, People magazine had named me the Sexiest Man Alive, and now, 10 years later, I looked to all the world like a madman.’

Nick pleaded no contest to charges of driving under the influence, and was given three year probation and ordered to undergo alcohol and drug counselling.

Bruno Mars

In 2010, Bruno Mars was arrested in a bathroom of the Hard Rock Hotel & Casino in Las Vegas, Nevada for felony cocaine possession

In 2010, Bruno Mars was arrested in a bathroom of the Hard Rock Hotel & Casino in Las Vegas, Nevada for felony cocaine possession

In 2010, at the height of his fame, Bruno, real name Peter Gene Hernandez, was arrested in a bathroom of the Hard Rock Hotel & Casino in Las Vegas, Nevada for felony cocaine possession, and posed for a beaming mug shot.

Bruno pled guilty to 2.6 grams of cocaine possession, and under his plea deal, charges were eventually dismissed after he paid a $2,000 fine and completed 200 hours of community service and eight hours of drug counseling.

Speaking about the arrest, he told GQ Magazine in 2013: ‘I was young, man! I was in f*****g Vegas. I wasn’t thinking. 

‘I was given a No. 1 record and I’m out doing dumb s**t.’

Jussie Smollett 

After rising to fame as a star of the FOX series Empire, Jussie Smollett's career came to a halt when he handed himself into police after lying to police about a homophobic attack

After rising to fame as a star of the FOX series Empire, Jussie Smollett’s career came to a halt when he handed himself into police after lying to police about a homophobic attack

After rising to fame as a star of the FOX series Empire, Jussie’s career came to a grinding halt when he handed himself into police on charges of filing a false police report. 

At the time the star had claimed that he was the victim of homophobic, racist attack on himself, but it later emerged that he staged the attack and lied to police about it.

Jussie was sentenced to 150 days in jail after a jury found he lied to police, and included 30 months of probation and $145,000 (£110,000) in restitution and fines.

Following the sentence, Smollett said: ‘I did not do this!’