Leonardo DiCaprio’s Hollywood evolution: then-and-now in 11 career-defining photos

Leo made his screen debut at just 15 years old, appearing in two episodes of The New Lassie in 1989. He then went on to appear in episodes of The Mickey Mouse Club and Santa Barbara in 1990, before securing the role of Garry Buckham on Parenthood, the short-lived TV spin-off of the popular 1989 film.

Leo’s on-screen mother in the show, played by Joanna Kerns, remembered Leo as a brilliant actor but also “totally mischievous”, adding that his good friend, Tobey Maguire, would often pop by the set, where the pair “looked like they were really up to no good”.

Leo made his film debut at just 16 years old in the direct-to-video comedy horror film Critters 3 (1991), also beginning his year-long run as Luke Brower in the sitcom Growing Pains the same year, a show which Brad Pitt also famously appeared in during his early years. 

Leo’s film career took off in 1993 after starring in This Boy’s Life alongside Robert De Niro; while he initially came to read for a more minor role, Robert himself told People that he went up to director Art Linson and said, “‘That kid had something special’” after Leo’s audition, gently encouraging the director to pick Leo for the leading part. 

That same year, he played the role of Arnie Grape in the Johnny Depp-led What’s Eating Gilbert Grape, which earned him his first Academy Award nomination for Best Supporting Actor – and began a decades-long string of perceived Oscars snubs.

In 1996, Leo charmed teen girls worldwide after appearing as the dashing Romeo in Baz Luhrmann’s  Romeo + Juliet, opposite Claire Danes. Leo flew to Australia with a bunch of actor friends to audition for the role, and while Baz didn’t reveal in his iHeart Radio interview who they were, it’s possible they were the infamous (and crudely named) “Pussy Posse”, Leo’s ‘90s acting crew consisting of stars like David Blaine and Tobey Maguire.

“When I saw Leonardo I thought, ‘God, that’s how he should look,” Baz said. “I realised that I couldn’t make it [Romeo + Juliet] without him.”

With a slew of history-making starring roles, it can be hard to choose just one to define Leo’s career – but it would probably have to be James Cameron’s Titanic (1997). As the roguish, blue-eyed charmer Jack Dawson opposite Kate Winslet’s Rose, his emotional performance and tragic end continue to break the hearts of both first-time viewers and avid rewatchers to this day.

While arguably the biggest hit of his career, James Cameron told People at the 2023 Golden Globes that he had to really “twist his arm” to convince Leo to appear in the movie. “He didn’t want to do a leading man,” Cameron said. “He didn’t want to do it [Titanic]. He thought it was boring.”

Evidently, James made the right call in convincing Leo, as it’s impossible to imagine anyone else telling Rose to “Never let go”.

With his most successful roles being swoonworthy leading man types, Leo went into the 2000s using his astronomical fame to choose more alternative roles in films that appealed to him and challenged him as an actor.

As the vengeful gangster Amsterdam Vallon in Gangs of New York (2002), Leo not only shook the mould of his romantic lead image but began a decades-long collaboration streak with Martin Scorsese, with the acclaimed director calling Leo “one of the greatest actors in the history of movies” at a National Board of Review award ceremony in 2024.

Leo continued forging a new acting niche for himself when he went on to star as an undercover cop in The Departed in 2006, as well as the gunrunner and diamond smuggler Danny Archer in Edward Zwick’s Blood Diamond the same year. 

A longtime environmentalist since establishing the Leonardo DiCaprio Foundation in 1998, Leo wrote and produced his first documentary film in 2007, The Eleventh Hour, which explored the consequences of global warming. The film included interviews with a range of politicians and activists, from former Soviet leader Mikhail Gorbachev to scientist Stephen Hawking, showcasing Leo’s storytelling talents behind-the-scenes.

As well as several more films with high-profile auteur directors, from Ridley Scott’s Body of Lies (2008) to another Scorsese collaboration with Shutter Island (2010), Leo also reunited with Kate Winslet in Revolutionary Road (2008), another romantic drama that sees the Leo-Kate pairing take an emotional battering…

Leo led the star-studded cast of Christopher Nolan’s mind-bending sci-fi film Inception in 2010, which received eight Academy Award nominations and won four – though sadly none for Leo. He later starred as former FBI director J. Edgar Hoover in J. Edgar (2011), directed by Clint Eastwood, and joined Jamie Foxx and Samuel L. Jackson in Quentin Tarantino’s revisionist Western film Django Unchained (2012). 

Reflecting on his first film with Tarantino, DiCaprio recalled a moment when his hand started bleeding during a scene, which the cast and crew initially thought was scripted. “My hand started pouring blood all over the table,” Leo said. “Maybe they thought it was done with special effects. I wanted to keep going”. After he finished his take, he received a standing ovation from everyone on set. 

Leo took on the roles of two very different millionaires in 2013. He reunited with Romeo + Juliet director Baz Luhrmann to take on the literary role of Jay Gatsby in The Great Gatsby, a reimagined adaptation of the classic F. Scott Fitzgerald novel – a role which he almost turned down.

Leo, who had read the book in high school, was understandably nervous about taking on one of literature’s most divisive characters – until Baz brought him a first edition of the novel and encouraged him to read it with fresh eyes.  

After starring in the opulent Roaring Twenties flick, Leo portrayed stockbroker Jordan Belfort in The Wolf of Wall Street, reuniting once again with Martin Scorsese. Viewed by some fans as his best movie to date, namely for his over-the-top performance and chemistry with Margot Robbie, this sadly didn’t score Leo an Academy Award, bringing his total nominations for Best Actor to four.

Film fans around the world cheered when Leo finally got the Best Actor award for his performance as frontiersman Hugh Glass in The Revenant (2015). After years of internet memes about the injustice of Leo having never received the industry’s highest accolade, social media was buzzing with news of his win, while Leo took the opportunity to speak about climate change during his acceptance speech.

Speaking about the gruelling filming process to Frame by Frame, Leo said: “There was a day I had to come out of a frozen river, and the bear fur, I had to walk with it up a hill. Your body is sort of slowly freezing. I don't know how these men did it.”

While he joked that he wouldn’t like to experience that again, he added “that’s what we knew we were signing up for” and described the experience as “a pretty memorable, profound, difficult one”. 

An Oscar well and truly earned!

Leo reunited with Quentin Tarantino and Margot Robbie in 2019 for Once Upon a Time…in Hollywood, which earned him another Academy Award nomination for Best Actor. For his role as fading actor Rick Dalton, Leo convinced Tarantino to let him “forget the lines” for the famous meltdown scene, and while the director wasn’t initially sold, he later told Deadline, “He was right. It was terrific, and it gave the whole thing an arc that worked wonderfully.”

Leo also starred in Killers of the Flower Moon, his sixth Scorsese film, in 2023, an anti-Western crime drama that was edged out for a Best Picture Oscar by Oppenheimer. The film also marked the tenth collaboration of Leo with Robert De Niro, who had witnessed Leo’s raw stardom over 20 years ago. 

As well as acting, Leo also continued his successful producing career with Ozi: Voice of the Forest the same year, an educational animated film about deforestation starring Laura Dern and Donald Sutherland, being the latter’s final role before he passed away in 2024.

While we’re all eager to see Leo in Paul Thomas Anderson’s One Battle After Another, which you can catch in cinemas now, does the legendary actor have any more films lined up?

Good news – Scorsese has officially cast Leo opposite Jennifer Lawrence in the upcoming film What Happens At Night, an adaptation of Peter Cameron’s 2020 horror mystery novel. While it hasn’t entered production yet, it’s set to follow a couple who travel to a snowy European town to adopt a baby – and we can expect that things aren’t going to go as planned.