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Top 10 Celebrities Who Surprisingly Have Mugshots!

VO: Rebecca Brayton
Script written by Q.V. Hough Everyone has seen the celebrity mugshots from the likes of Lindsay Lohan, Matthew McConaughey and Robert Downey, Jr. But did you know that more seemingly “innocent” celebrities like Shailene Woodley, Bill Gates, Reese Witherspoon, Hugh Grant, Hailey Joel Osment, Keanu Reeves and Jane Fonda have also been arrested and taken part in the timeless ritual of the mughsot? Hell, even Tim Allen aka Tim “The Tool Man” Taylor was arrested back in the day, and you won’t believe what he was arrested for!

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Top 10 Celebrities Who Surprisingly Have Mugshots!

We know these Hollywood names for their work, but we didn’t anticipate their most infamous headshots. Welcome to, and today we’ll be counting down our picks for the Top 10 Celebrities We’re Surprised Have Mugshots.

For this list, we’re not counting down the most hilarious mugshot images. Rather, we’re focusing on celebs that don’t seem like trouble, at least in terms of the legal system and as such, leave us shocked with these discoveries..

#10: Vince Vaughn

From a critical perspective, one could argue that the 2001 film, “Domestic Disturbance,” is a cinematic crime. With that being said, its star, Vince Vaughn, got caught up in a real crime story while filming the flick in Wilmington, North Carolina. According to reports, a couple locals didn’t appreciate Vince’s late night chat with their female friend. Upon going outside, things got nasty as Vince’s pal and co-star, Steve Buscemi, received several stab wounds. While that’s crazy enough, Vince Vaughn’s surprising mugshot insinuates that he might’ve been wilding out long before the first punch.

#9: Hugh Grant

As an actor, this man has built a solid career based on his charming ways and endearing onscreen persona. Unfortunately for Hugh, along with ex-girlfriend Elizabeth Hurley, he got arrested in 1995 after hooking up with a Los Angeles sex worker. Hugh’s mugshot shows a slightly embarrassed man; a gentleman realizing that he just may have some explaining to do. Since the arrest, Hugh’s continued to sustain a lasting career. However, his sexcapade remains a surprising story in his personal narrative arc. But at least he doesn’t look as blitzed as Vince Vaughn.

#8: Shailene Woodley

In 2016, Hollywood actors, activists, and even some old-fashioned hippies protested against the Dakota Access Pipeline. But it was American starlet Shailene Woodley that received the most attention, as she and 26 others were hauled off to Morton County Jail for criminal trespassing, leading to her rather normal mugshot. Woodley later released an extensive statement about her Facebook Live stream, challenging Americans to think harder about the issue at hand. Regardless of one’s opinion on the matter, Shailene obviously stayed true to the cause, as evidenced by her surprising arrest.

#7: Reese Witherspoon

Known for her lively onscreen charisma and iconic characters, this Oscar-winner actress seems like just a normal gal. But when Reese Witherspoon’s husband got busted for a DUI in 2013, she had a few issues with the legal process. In fact, Reese challenged the arresting officers a little too much, which prompted her to drop the celebrity card. It also meant some (very brief) jail time and a mugshot, the latter of which spoke volumes about her questionable behavior. Not only does Reese seem quite embarrassed, but she also seems to understand that celebrities aren’t immune to the legal system when they’re blatantly obstructing justice, if only out of confusion and surprise.

#6: Macaulay Culkin

In “Home Alone,” this actor played the sly and tactical Kevin McCallister. By 2004, however, Macaulay Culkin had moved past his most famous character and hooked up with Mary Jane, otherwise known as marijuana. That year, he was as a passenger in a car that was speeding on an Oklahoma City freeway, which prompted a ticket from the local 5-0. They not only found marijuana in the Pontiac Bonneville, but a variety of controlled substances without a prescription - and so Macaulay got LOCKED UP. This surprising mugshot clearly shows that Culkin had been fully enjoying himself, with the smirk almost giving the impression that he’s still “in character,” so to speak.

#5: Tim Allen

Before this man evolved into Tim “The Tool Man” Taylor on ABC’s “Home Improvement,” he was going by his birth name, Tim Allen Dick. At the age of 25, cocaine played a somewhat notable role in Tim’s life, as the man got pinched by the police with 650 grams at the Kalamazoo/Battle Creek International Airport. Allen ultimately served only 28 months after naming names, and he also provided a surprising mugshot, at least given the contrast between 1978 Tim Allen and celebrity Tim Allen. There’s a look of resignation, as Tim seems both relieved and aware that he’s about to serve some hard time.

#4: Haley Joel Osment

In 2006, this former child actor got drunk and stoned, crashing his station wagon after a Los Angeles concert. Thankfully, Haley Joel Osment didn’t injure anybody during his ill-advised journey, although he did suffer a broken rib during the flip. And so, the bittersweet relief shows in his smiley mugshot. At the time, the 18-year old actor wasn’t exactly a hot commodity in Hollywood, and the next few years wouldn’t get any more exciting. So, this celebrity mugshot essentially marks the end of the “I See Dead People” era, as Haley Joel was no longer a juvenile, but a man forced to deal with his boozed-up mistake.

#3: David Bowie

At the age of 29, this iconic rock star was arrested for marijuana possession at the Americana Rochester Hotel in New York. And while he was booked under his birth name, David Jones, the mugshot is pure Bowie through and through. It almost doesn’t seem real, as the image feels like it could be an album cover or a promotional image. In fact, it wasn’t actually taken on the night of the arrest – it came three days later, allowing Bowie to glam up for his city court appearance. And that he did, producing a rock star mugshot for his Monroe County marijuana incident.

#2: Bill Gates

Believe it or not, this Microsoft mogul was reportedly arrested twice between 1975 and 1977. On both occasions, Gates got busted for driving without a license. There are a few things to consider with this surprising celebrity mugshot from 1977 though, whether it’s the style, the specs, or Gates’ state of mind at the time. What makes it truly unique, as noticed by Ars Technica editor-in-chief Ken Fisher, is that the image seems to have inspired the outline for future Microsoft applications… which means that we’ve supposedly been looking at Gates’ mugshot time and time again for years.

Before we unveil our top pick, here are a few honorable mentions.

Keanu Reeves
Arrested for DUI (1993)

George Carlin
Arrested for Public Indecency for Violating Obscenity Laws (1972)

Jane Fonda
Arrested for Drug Smuggling and Assaulting an Officer (Both Charges Dropped) (1970)

#1: Frank Sinatra

In the late 1930s, this young crooner made 15 dollars per week as a singing waiter. And while many knew Frank Sinatra for his smooth voice, the Bergen County police knew him for his “sex crimes” aka “seduction” and “adultery.” In other words, Frankie got busted for hooking up with a married woman – though both chargers were later dismissed. As for the mugshot, well, it shows the striking presence of Sinatra back then, all stoic and confident. Of course, there’s something lacking, too, and that’s his classic blues. However, the black and white image is now classic all the same.

Do you agree with our list? Which celebrity mugshot surprises you the most? For more jaw-dropping Top 10s published daily, be sure to subscribe to

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