Look Back at the '90s Breakout Roles of Leonardo DiCaprio, Julia Roberts and More of Today's A-List Stars

90s Breakout Roles

Disney Enterprises, Buena Vista Pictures, ABC

What do Julia Roberts, Leonardo DiCaprio and Reese Witherspoon all have in common?

Believe it or not, these stars were once considered up and coming actors trying to get that big break in Hollywood.

While they may be able to live in multi-million dollar homes or carry Oscar trophies around today, many A-list talent shining upon us now didn’t become household names until the ‘90s.

Before fans knew her as Bridget Jones, Renée Zellweger appeared in a special movie titled Dazed and Confused. And before Johnny Depp and Captain Jack Sparrow were synonymous with each other, the actor had an unforgettable role in Cry Baby.

Is it all coming back to you now?

In celebration of ‘90s nostalgia week at E! News, we’re taking a look back at the breakout roles of today’s biggest stars. It’s one wild trip down memory lane.

Julia Roberts, Pretty Woman

No one expected much from the modestly-budgeted romantic comedy. But as it turns out, it turned Julia into one of America’s sweethearts.  

Johnny Depp, Cry Baby

The irresistible bad boy captivated audiences with the impressive ability to shed one single tear. It also got the ladies including Allison Vernon-Williams all hot and bothered. 

Cameron Diaz, The Mask

At just 21 years old, the actress appeared as Jim Carrey‘s love interest and made the role of Tina Carlyle her own. She would go on to earn roles in Shrek, There’s Something About Mary and Charlie’s Angels.  

Matt Damon, Good Will Hunting

“I was gonna be getting out of school in two or three months when I got a part in the movie Geronimo: An American Legend. I went out to Los Angeles and stayed with Ben Affleck,” Matt once revealed when discussing the origin of his breakout role. “I slept on his floor. I brought my Act I of the Good Will Hunting script and gave it to him.” The rest they like to say, is Hollywood history. 

Sandra Bullock, Speed

Call it the start of a beautiful box office pairing. Fans couldn’t get enough of the bond between Sandra and co-star Keanu Reeves on the big screen. “Generally [Keanu] tends toward dreamy, sensitive characters. That’s why it’s sort of amazing to see him so cool and focused here, a completely convincing action hero,” the late Roger Ebert once said. “He and Bullock have good chemistry; they appreciate the humor that is always flickering.” 

Leonardo DiCaprio, Growing Pains

Sometimes, it’s the roles on the small screen that get the biggest attention. Shortly after starring in Critters 3, Leo appeared in the ABC sitcom where he played a homeless student named Luke Brower. 

Renee Zellweger. Dazed and Confused

So she wasn’t the big star in this project. But she sure left an impression on the big wigs. “Renee didn’t quite get the bigger part, but it said a lot about her that she just sort of hung out and was there,” director Richard Linklater once told USA Today. “At some point, she was kind of a cast member. It was a technicality that she doesn’t have a line.”

Jake Gyllenhaal, City Slickers, 90s Breakout Roles

Metro-Goldwyn-Mayer Studios Inc.

Jake Gyllenhaal, City Slickers

He may have had a small role in the big-screen project, but to this day, Jake has nothing but positive memories from the set. “There’s a lot from my childhood that I don’t remember, and I remember everything from that,” he shared with EW

Lindsay Lohan, The Parent Trap

She may have her ups and downs in the public eye, however, there’s no denying the raw talent displayed by Lindsay in the Disney classic. Besides, without this role, who knows if we would have had the actress in Mean Girls

James Franco, Never Been Kissed 

Long before scoring parts in 127 Hours, Spring Breakers and Spider-Man, the actor got his first major movie role in the 1999 film. 

Reese Witherspoon, The Man in the Moon, 90s Breakout Roles

Metro-Goldwyn-Mayer Studios Inc.

Reese Witherspoon, The Man in the Moon 

Before she was Elle Woods in Legally Blonde, Cheryl in Wild or June Carter in Walk the Line, Reese impressed critics and moviegoers alike with her role as Dani Trant in the 1991 film. 

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