The 20 Ugliest Celebrity Mug Shots

Heather LocklearHeather Locklear looks far less glamorous in her booking photo.

Celebrities usually look good even when they’re behaving badly – but sometimes they get caught off guard.So after showing you sexy celebrities who looked as good as ever even in their mug shots, here are some famous people who didn’t.

Probably not the Anna Nicole Smith you're used to seeing. She was arrested in 1989 for drunk driving and has this mug shot to show for it.

Mug shot via The Smoking Gun

Mug shot via The Smoking Gun

Mug shot via About.com

Hugh Grant looks pretty sheepish in his 1995 mug shot after he was allegedly caught having sex with a prostitute.

Mug shot via The Smoking Gun

Mug shot via TMZ, Arrest info according to USA Today

Mug shot via The Smoking Gun

Heather Locklear looks pretty bewildered in this 2008 mug shot. She was arrested for alleged DUI.

Mug shot via The Smoking Gun

Mug shot via The Smoking Gun

Mug shot via The Smoking Gun

Robert Downey Jr. looks like hasn't slept in weeks. He was arrested in 2000 for drug possession.

Mug shot via New York Daily News

The usually flashy looking Wynonna Judd doesn't have the same flare as she poses for this 2003 mug shot. She was arrested for drunk driving.

Mug shot via The Smoking Gun

A scruffy and dazed-looking Daniel Baldwin poses for a 2006 mug shot. He was arrested on drug possession charges.

Mug shot via The Smoking Gun

Vince Vaughn looks like he had a really rough day. Which he probably did after being charged in 2001 with fighting in public.

Mug shot via The Smoking Gun

Mug shot via The Smoking Gun

Nick Nolte's hair is all over the place as he poses for this 2002 mug shot after getting arrested on DUI charges.

Mug shot via The Smoking Gun

Mug shot via About.com

Kid Rock has a number of bad mug shots. The top one is from 2007, and the one beneath is from 2005. The lower left is from 1991 and the one on the right is from 1997.

Mug shot via The Smoking Gun

Mug shot via About.com

Informercial king Vince Shlomi doesn't look as energetic as usual after getting arrested in 2009 for allegedly punching a hooker. He claimed she bit his tongue and wouldn't let go.

Mug shot via The Smoking Gun

Rapper DMX, whose real name is Earl Simmons, has probably seen better days. He poses in this 2008 mug shot following his arrest on drug and animal-cruelty charges.

Mug shot via Los Angeles Times

Now check out someone some bank robbers who always try to look their best.

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