After a televisual debut in Parenthood in the early 1990s, Leonardo DiCaprio became one of Hollywood’s most promising prodigies as several spellbinding performances funnelled wind into his sails. Most notably, DiCaprio drew the attention of directors in 1993 with two breakout roles: This Boy’s Life, where he acted opposite Robert De Niro, and What’s Eating Gilbert Grape, in which he flawlessly portrayed Johnny Depp’s titular character’s developmentally disabled brother.

By the mid-1990s, DiCaprio had received further praise for performances in The Basketball Diaries and Romeo + Juliet. Still, it was an appearance in James Cameron’s landmark blockbuster Titanic in 1997 that sealed his fate as the most sought-after leading man in contemporary cinema.

By the turn of the millennium, DiCaprio had Hollywood at his heels and could swing a role in practically any production. Following an appearance in Danny Boyle’s poorly received adaptation of Alex Garland’s novel The Beach in 2000, DiCaprio sought a bonafide blockbuster in which to bounce back.

At this juncture, George Lucas contacted DiCaprio as his first choice for the role of Anakin Skywalker in the final two movies of the Star Wars prequel trilogy. While the opportunity would have doubtless come with armfuls of cash and a great deal of exposure, the young star didn’t see his future as a sci-fi franchise star.

“I did have a meeting with George Lucas about that, yes,” DiCaprio told Shortlist in 2015. “I don’t think I was ready for anything like that. I just didn’t feel ready to take that dive. At that point.”

In the same conversation, DiCaprio revealed that he had been in similar talks for a role as Robin in Batman Forever and his friend Tobey Maguire’s role in Spider-Man. “That was another one of those situations, similar to Robin, where I didn’t feel ready to put on that suit yet. They got in touch with me,” he said in response to questions about the Spider-Man role.

In 2002, the same year Hayden Christensen starred as Anakin Skywalker in Star Wars: Episode II – Attack of the Clones, DiCaprio appeared in a leading role in Martin Scorsese’s Gangs of New York. Appearing alongside the likes of Daniel Day-Lewis and Cameron Diaz, the movie further raised DiCaprio’s Hollywood status and crucially kindled his essential relationship with Scorsese.

Since 2002, DiCaprio has starred in four further full-length movies directed by Scorsese and is soon to appear in another, Killers of the Flower Moon. Watch the trailer below.