The 1990s was a decade of dramatic change for Hollywood, with the industry building off the franchises and star power of the previous decade. With audiences caring more and more about the most stylish celebrities, the ‘90s gave rise to such icons as Sandra Bullock, Julia Roberts, Keanu Reeves, Johnny Depp and Leonardo DiCaprio, with each one seizing the opportunity to dramatically rise to the pinnacle of the entertainment industry using a balance of talent and media training.

Such can be seen clearly reflected in the career of DiCaprio, who entered the industry in 1991 as a burgeoning 17-year-old and exited the decade as one of Hollywood’s most bankable stars. Careful in the projects he chose to take on, DiCaprio was somewhat lucky that he was handed artistic legitimacy early in his career, collaborating with Robert De Niro during only his third feature film project.

Released in 1993, This Boy’s Life remains one of DiCaprio’s most underrated feats of acting, with the young star playing a teenager who struggles to mature while living with his abusive stepfather. “Watching Robert De Niro on set, seeing his dedication, was one of the most influential experiences of my life,” DiCaprio later said of the tough love De Niro gave him at such a young age, giving him the foundations to build a highly successful career.

Following This Boy’s Life and What’s Eating Gilbert Grape of the same year, for which DiCaprio gained an Oscar nomination, his rise to the cream of the Hollywood crop was pretty straightforward. After a few middling dramas, he took a role in Baz Luhrmann’s Romeo + Juliet in 1996, which enchanted a whole generation of young teenagers, then, for good measure, made the highest-grossing movie of its time with James Cameron’s Titanic.

Though maybe his rise to success took more nuance than people give him credit for, after all, behind every good career is a host of great decisions. One such choice was made early in the 1990s when DiCaprio decided to turn down what would later become a fan-favourite Disney flick, telling Movieline in a printed interview from 1995 that he didn’t think much of 1993’s Hocus Pocus when the script was slapped in front of him.

“I just felt like doing a movie is doing a movie; I get money and fame, and that’s great, and I can act and have fun,” DiCaprio started, adding, “I was up for a movie called Hocus Pocus with Bette Midler, and I knew it was awful, but it was just like, ‘Okay, they’re offering me more and more money. Isn’t that what you do? You do movies, and you get more and more money.’”

Everyone around the actor was confused as to why he didn’t want the project at the time, with DiCaprio finally saying to himself, “‘Okay, I’ll audition for this movie Gilbert Grape. If I don’t get that, I’ll do Hocus Pocus.’”

As fate would have it, he indeed got the role in What’s Eating Gilbert Grape, a film that would elevate his critical profile in Hollywood. Yet, this isn’t to say that he wouldn’t still have been a star if he’d taken a role in the dark comedy movie. But, then again, considering that the actor who played the role he would have had in the Disney flick Omri Katz never amounted to much, it seems that DiCaprio may have been wise beyond his years.