Hilariously Awkward Celebrity Red Carpet Photos From Their Early Days In The Limelight

Have you ever compared yourself to Hollywood royalty and thought, "how do they always look so gosh darn perfect?" If this sounds familiar, then wallow no longer! As it happens, even the most famous stars haven't always been so effortlessly cool. And luckily for you, we've scoured the depths of the internet to find the earliest showbiz appearances of the most glamorous stars out there. Spoiler alert — plenty of them must have worked seriously hard to cultivate their ultra-chic 21st-century demeanor. It's time to delve into the A-lister archives and reveal the red carpet photos these stars might be wishing had never been taken. 

George Clooney

When: 1989

Where: Steven Cannell's 10th Anniversary Party

In 1989, George Clooney was just another hard-working TV actor fresh off his stint on Roseanne. Nobody knew that he would one day be a total A-lister. Except for maybe George himself... look at that smirk! We can only assume his low-key suit and jazzy tie were an attempt to disguise his star charisma.

Angelina Jolie

When: 1986

Where: The Academy Awards

Angelina Jolie may be Hollywood royalty today — and always a vision of perfection — but this wasn't always the case. This photo, taken in 1986, shows when Angelina was still just actor Jon Voight's shy and adorable kid. Her older brother James Haven is in the background and mom Marcheline Bertrand is just out of shot. Nothing beats a full family affair for your first red carpet!

Ashton Kutcher

When: 1999

Where: Varsity Blues Los Angeles premiere

While today's Ashton Kutcher might have somehow managed to convince everyone that he's hunky, cool, and perpetually hip, never forget 1999 Ashton Kutcher who never met a camera he didn't flash the peace symbol for. Well, if it helped him to couple up with Mila Kunis, then maybe he was doing something right after all. In 1999, he was about one year into That '70s Show, so his star was clearly on the rise.

Emma Watson

When: 2001

Where: Harry Potter and the Sorcerer's Stone premiere

Today, Emma Watson isn't just a well-established and respected actress; she's also a political advocate with the brains to prove it. This 2001 picture of her at the height of her slightly awkward youth is a reminder of just how fast those darn kids grow up! Known for her unique blend of classic and ultra-modern looks, Emma's come a long way from that purple boa and gold lamé clutch.