The most memorable Leonardo DiCaprio roles

The first time a young DiCaprio popped was in a movie that was very much a Johnny Depp vehicle. It’s a very ‘90s drama about a young man dealing with a fraught family life in a small town. DiCaprio’s boyishness helped, as he was able to play younger at 18, which probably made his work seem more impressive. His turn as a “mentally disabled” kid (his disability is that sort of nebulous movie conception) earned him an Oscar nomination.

Baz Luhrmann, as is his want, made a bugnuts, over-the-top version of one of the best-known plays in history. Pretty much everybody knows “Romeo and Juliet,” but what if you put a plus sign in the title and modernized it and threw in a bunch of guns and stuff? The insanity didn’t even matter, because teenagers were too busy being smitten by DiCaprio and Claire Danes and turned this movie into a hit. Those who were of a certain age in the ‘90s often still can’t separate assessing the quality of the movie from their formative crushes.

Ever heard of it? DiCaprio was minted as a movie star with “Titanic.” It was, at the time, as big a cinematic sensation as there has ever been. James Cameron’s film about, well, the Titanic, had romance, epic drama, and that one Celine Dion song. It won 11 Oscars, became the highest-grossing movie in history, and ensured DiCaprio would be a big thing on the big screen.

“The Beach” is memorable as a film that pushed the limits of DiCaprio’s stardom, and also arguably marked the end of his “young heartthrob” era and pushed him into “serious adult actor.” Danny Boyle directed the movie at a time when he was still able to ride the wave of “Trainspotting.” The film landed strangely. It did well at the box office, because DiCaprio was in it, but it wasn’t a major hit. Critical assessment was mixed. Teenagers coming for their crush on Leo were left with a lot to unpack. “The Beach” was a turning point.

For years, Robert De Niro was Martin Scorsese’s main collaborator. Then, that torch was passed to DiCaprio, and that started with “Gangs of New York.” The period drama is not peak Scorsese. It’s a bit overlong, and Cameron Diaz was miscast. DiCaprio showed he could hold his own, though, which is impressive given that he was going toe-to-toe with one of the best to ever do it in Daniel Day-Lewis.

DiCaprio had aged up enough that the youthifying of him to play young Frank Abagnale Jr. felt uncanny at times. And yet, we only care so much. “Catch Me If You Can” is a rollicking drama from Steven Spielberg. It can be fun. It can be heartbreaking. DiCaprio and Tom Hanks soar in the movie, the kind of critically-acclaimed crowd pleaser that has become increasingly rare.

“When will DiCaprio win an Oscar?” was starting to bubble up as a question around this time. Once again, Scorsese and DiCaprio collaborated, this time with a sweeping biopic of Howard Hughes. It felt like Oscar bait, and it was, but it was well-crafted Oscar bait. “The Aviator” is a very good film, and it did work at winning an actor an Academy Award. It just happened to be Cate Blanchett, not DiCaprio, who won it. Because Cate Blanchett rules.

DiCaprio was stacking up helping others win Oscars! To be fair, “When will Scorsese win an Oscar?” had been a question for decidedly longer. It was a long time coming, and it finally happened. “The Departed” is more of an elevated crime thriller than a cinematic masterpiece, but it’s well done to be sure. It’s just surprising that this is the one that won Scorsese his Best Director and his Best Picture. Also, it’s still his only win on both fronts! DiCaprio is good in “The Departed,” but this was never going to be an Oscar winner for him.

Christopher Nolan is a dude who will properly cash the blank checks Hollywood gives him. He had crushed it with two Batman movies, so he said to Warner Bros. “I’m going to make a heist movie set in dreams that makes no sense if you think about it for two seconds.” The studio said, “Cool,” and it worked out for everybody. “Inception” was a massive hit and a popular movie. DiCaprio got to star in a “smart” blockbuster and work with another burgeoning acclaimed director. In terms of broad appeal and popularity, it’s probably second only to “Titanic” among Leo’s movies.

We posit this: If not for DiCaprio, “The Great Gatsby” would not have been a memorable movie. Baz Luhrmann was able to cash in his favor for giving DiCaprio one of his first big roles to have him play the titular Jay Gatsby in his, naturally, bananas adaptation of the famed F. Scott Fitzgerald novel. It looks remarkable, and thanks to the presence of DiCaprio it was a hit. Plus, we got the meme. DiCaprio is the reason the meme ever came into existence.

A sordid, vulgar, thorny movie centered on an amoral grifter…that made $400 million in theaters. The power of DiCaprio, and also to a degree the power of Scorsese. DiCaprio starred as Jordan Belfort in a movie packed with drugs, sex, depravity, and more. It’s inexplicable “The Wolf of Wall Street” was a hit, and we say that while also noting we think it’s a good movie. It was nominated for five Oscars, including for DiCaprio, but once again no trophy for Leo.

When it (arguably) takes too long to give an actor his Oscar, stuff like this happens. It’s not quite on the Jeff Bridges for “Crazy Heart” level, but this miserablist slog is far from DiCaprio’s best movie. He’s quite good in it, but it’s not a good movie set up around him. However, “The Revenant” will always be remembered, because it is the movie for which DiCaprio did, indeed, finally win Best Actor.

Imagine if the Academy hadn’t said “Fine, we’re sorry” and given DiCaprio his Oscar for “The Revenant.” He and Brad Pitt could have finally won their Oscars for “Once Upon a Time…in Hollywood.” This movie is light years better than “The Revenant,” a triumphant work of film from Quentin Tarantino, a director whose filmography we don’t full-throatedly endorse. DiCaprio is great as Rick Dalton, but instead the Oscar for Best Actor went to…Joaquin Phoenix for “Joker.” Sometimes we wonder why we care about the Academy Awards.

Scorsese brought DiCaprio and De Niro together for his searing drama focused on a series of murders among members of the Osage tribe that played a large part in the birth of the FBI. With his boyishness and matinee idol days behind him, DiCaprio could fully lean into age and also play an odious, boorish man. The film did not perhaps land as expected for any of the parties involved (especially Lily Gladstone when the name “Emma Stone” rang out at the Oscars), but it’s an impressive work of film that will be one of the last (and perhaps the last) from Scorsese.

As we wait to see how memorable “One Battle After Another” proves, let’s go back to the beginning. When family sitcoms run for a while, and as the kids get older, producers have to figure out what to do. “Growing Pains” had already pulled the “new baby” stunt in season four. For the seventh, and what proved final, season, the show tried something different. A homeless teenager named Luke Brower came to live with the Seavers for the seventh season, which aired in 1991 and 1992. Yes, Luke was played by DiCaprio. Well done, casting department.