How '90s Stars Became Some of the Biggest Names in Hollywood Today

Inside the decisions that led to nonstop work for some in Tinseltown

By Francesca Bacardi Oct 18, 2016 11:00 AMTags
Matt Damon, Ben Affleck, Leonardo DiCaprio, Julia RobertsGabbe/Getty Images, FABRICE COFFRINI/AFP/Getty Images, Kevin Winter/Getty Images, Jackson Lee/Splash News

It's a tough transition from child star to adult star.

Many child stars have gone on to disappear from Hollywood, taken a hiatus only to re-emerge as adults on the big screen or have taken an unfortunate turn and spiraled. There's no predicting what will happen to them, but some lucky stars go on to have long lasting careers.

But what about those actors and actresses who began their careers fairly late in life? Late in life for an actor being late teens to mid-20s, of course. Stars such as Julia Roberts, Ben Affleck, Matt Damon and Leonardo DiCaprio have been famous for what seems like eons, but they haven't skipped a beat.

Leo, for example, has had an eclectic career.  

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He began as a supporting cast member in Growing Pains in the 1980s and then skyrocketed to the '90s heartthrob hall of fame thanks to Titanic and Romeo + Juliet. But unlike other heartthrobs who have disappeared from Hollywood (looking at you, Jonathan Taylor Thomas) Leo continued to grow and grow, only to solidify himself as a leading man in Tinseltown.

So what's the secret? What did these stars do to maintain their careers? Perhaps it lies in the low-key hiatus.

After Leo became a household name thanks to Titanic and Baz Luhrmann's take on the classic Shakespearian tragedy, he went away. He already had an Oscar nomination under his belt thanks to a critically acclaimed role in 1993's What's Eating Gilbert Grape, so his talent level wasn't even remotely a question. 

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He also happened to be the love of many teens' lives, so maybe he didn't want to risk overexposure. As a result, he only took on a few roles between 1997 and 2002, appearing in The Man in the Iron Mask and The Beach.

While five years might not seem like a long time, in Hollywood that could be the start and end of someone's career. But for Leo, it wasn't; he burst back onto the scene in 2002's Catch Me if You Can with Tom Hanks and in Martin Scorsese's Gangs of New York, which would be the first of many collaborations with the revered director. Since then Leo has been a Hollywood icon who finally took home his first Oscar last year for The Revenant.

For Affleck, however, maybe the secret lies in chance and perseverance. 

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Like many actors before him, Affleck began his career in commercials when he was young. During that time he met Matt Damon, his future BFF and colleague.

His role in the feature film Dazed and Confused put Affleck's name on the map and ultimately led him to star in indie films such as Mall Rats and Chasing Amy, which gave him some acclaim at festivals such as Sundance.

Despite the seemingly growing career, Affleck's work started to take a hit. He, his younger brother Casey Affleck and Damon were all facing rejections at auditions, so Affleck and Damon wrote their own script and turned it into the Academy Award-winning Good Will Hunting. The rest, as they say, is history...well almost.

Affleck went on to star in some blockbusters, including Armageddon, Shakespeare in Love and Pearl Harbor. But his career took a downturn with movies such as Gigli.

Affleck even admitted that the movie, which also starred his former flame Jennifer Lopez, was a mistake. "People bring up 2003, and I get it. Jennifer Lopez, and Gigli, and all this s--t just kind of blew up," he told Details while explaining his comeback. "But, you know, in 2003, Barack Obama was a state senator in Illinois!"

Point taken.

Affleck went on to appear in He's Just Not That Into You and then co-starred, wrote and directed The Town. And in 2012, Affleck directed and starred in Argo, which earned him another Oscar. Even when the going got tough, Affleck persevered and came out on top.

His BFF Damon also had a tumultuous time rising to the top. Before Good Will Hunting, Damon appeared in Mystic Pizza, a movie that didn't do too well initially but became a beloved classic down the line, and School Ties, a certified classic.

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Miramax Films

But it wasn't until Good Will Hunting that his name became a fixture in Hollywood.

Damon went on to star in Steven Spielberg's Saving Private Ryan, one of the most critically acclaimed movies of the late '90s, but then decided to alternate roles in comedies and dramas. He proved that he could play either type of role seamlessly and managed to earn positive reviews for his acting in each movie, even if the film itself didn't do that well. But then Damon took his skills to the next level by taking on the action movie world with the future hit franchise The Bourne Identity starring main character Jason Bourne.

Even though he suffered some flops, Damon, like his Boston BFF, proved that perseverance could do a lot for an actor or actress' career. 

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But how do you get past a type cast? Roberts, a woman who has been one of Hollywood's sweethearts forever, will most likely forever be known as the romantic comedy queen. Roberts shot to fame with Mystic Pizza and Satisfaction in the late '80s, but really became a star with 1990's Pretty Woman. The iconic role earned her an Oscar nomination, and skyrocketed her to rom-com stardom with starring roles in movies such as My Best Friend's Wedding, Notting Hill and Runaway Bride.

Similarly to Damon, Roberts seamlessly weaved in and out of genres despite her knack for romantic comedies. Her starring role in the real-life drama Erin Brockovich nabbed her an Oscar, and her performance in August: Osage County also scored her a nomination.

Suffice it to say, America's Sweetheart (who also happened to star in a rom-com titled America's Sweethearts), made a lasting career by keeping her fans—and Hollywood—on their toes.

So what can these celebs teach us about how to make a long-lasting career in Hollywood? Maybe that it all comes down to a lot of hard work and a little bit of luck.