The best Leonardo DiCaprio roles of all time

It's worth showing a little love to Leo's true introduction to mainstream viewers. Just a teenager, DiCaprio joined the cast of the wildly popular ABC sitcom for its seventh and final season. Rough around the edges, Luke is a high school student Mike (Kirk Cameron) encounters during a teaching gig. It's determined that Luke is homeless, and the Seaver family takes him in. Though plenty of the stereotypical subject matters associated with a troubled, but intelligent, child are addressed, DiCaprio's performance was perhaps the best aspect of the show's grueling final run.

DiCaprio seemed to have no problem taking on this challenging portrayal of the controversial FBI director. It can be disturbing to watch at times, but, then again, that's a sign of an elite actor. DiCaprio certainly gave his all in the role, complete with plenty of makeup to age his character. When it was all said and done, DiCaprio comes through superbly on the Clint Eastwood picture that earned the popular actor a Golden Globe nomination for his work.

This was the first in a line of films for which DiCaprio teamed up with legendary director Martin Scorsese. Actually, the professional relationship the two forged might have been the best thing to come out of the film. The making of the movie dragged on, seemingly forever, much like the finished product (167-minute running time). This 1800s period piece about feuding Irish immigrants is way over the top, but DiCaprio’s performance as the young Vallon is truly the picture's saving grace. 

A rather underrated role for DiCaprio, who plays a misguided traveler in search of serenity on a foreign island. Richard comes off as simple enough on the surface, but his mind is intensely complex and kind of immature. There were plenty of professional film critics who slammed the movie, but this also served as an example of the wide range of emotional characters DiCaprio would come to be known for portraying. 

When we get right down to it, DiCaprio is brilliantly disturbing, though obviously intriguing, in this sci-fi action flick. Leo fans — and film critics — might consider this to be his most intelligent role, playing a thief who takes information from people’s dreams. The various plot twists can be confusing at times for those not completely invested while viewing, and the conclusion of the movie is rather perplexing. Still, DiCaprio is mesmerizing in a completely unique role.

There was plenty of hype surrounding this modernized version of the famed star-crossed lovers' tragic tale. It did gross $51.8 million, so plenty were willing to get caught up in it all. However, it just seemed the movie was too over-the-top and grandiose. Yet, DiCaprio and co-star Claire Danes, two of the most popular young actors at the time, were highly believable and sympathetic while taking on these legendary title characters.

Putting DiCaprio together with Robert De Niro, at the time, might not have been a big deal. However, the talented young actor more than held his own while depicting a young Tobias Wolff in the adaptation of the famed writer’s memoir. De Niro and DiCaprio provide most of the movie's most memorable moments. Like other movies in DiCaprio's arsenal, this can be tough to watch at times, but rewarding when all is said and done.

As we'll see later on this list, DiCaprio and Kate Winslet are better known for starring together in that movie about an ill-fated luxury liner. Yet, they are more than serviceable in their big-screen reunion. Each was nominated for a Golden Globe as a couple watching their marriage fall apart. It’s nowhere near the same type of love story the pair is best remembered for sharing, but their collective performance here is simply stellar considering the complex nature of these characters.

DiCaprio's second Best Actor Oscar nomination came for his role as a gun-runner and diamond smuggler in this Edward Zwick-directed action war film. Perhaps that note was forgotten by everyday movie fans. Within DiCaprio's vast filmography, Blood Diamond tends to get lost among his more notable and popular movies. Yet, this is time well spent. Then again, 2006 was a pretty good year for DiCaprio when it come to putting out memorable films.

A sign of an exceptional actor is when the characters they play are disturbing to watch. With The Basketball Diaries, it’s uncomfortable and captivating to see DiCaprio portray the real-life Carroll’s downward spiral into the world of hard drugs. Now, the movie hasn't necessarily aged well, but DiCaprio continues to be praised for how he handled the chameleon-like Carroll. It was one of the first real signs of the talent DiCaprio possessed. It's not an easy watch, but grippingly good to be celebrated.

It made sense that DiCaprio and Quentin Tarantino would hook up for a film at some point in their careers. When it happened, both knocked it out of the park with Django Unchained. DiCaprio is weirdly captivating as the sinister plantation owner, starring alongside fellow Hollywood heavyweights Jamie Foxx and Christoph Waltz. He's responsible for stealing many a scene throughout the film and might have been worth some Oscar love in the process. 

Here we go with DiCaprio and Scorsese taking on another project together. This one earned Leo a Best Actor Oscar nomination. Certainly, Hughes is not somebody easy to like in real-life, but DiCaprio manages to humanize the persona and makes the eccentric and reclusive mogul seem genuinely sympathetic. While DiCaprio did not win the Academy Award for this role, he recorded his first of three Golden Globe wins as an appropriate consolation prize.

DiCaprio's most recent Academy Award nomination came for this role as an aging actor and former Hollywood Western star looking to keep his career alive. In another collaboration with Quentin Tarantino, the genuine honesty DiCaprio gave to Rick Dalton is what's most memorable about this fictional tale interwoven within the backdrop of the real-life Manson-Tate murders. Dalton's scene with child actor Trudi Frazier (brilliantly played by Julia Butters) might be the highlight of the film.

Adam McKay's science-fiction satire of the United States government's indifference to climate change features quite the ensemble cast: Jennifer Lawrence, Cate Blanchett, Jonah Hill, Tyler Perry, and Meryl Streep, to name a few. Yet, DiCaprio arguably stands out among the rest, and was rightfully nominated for a Best Actor Golden Globe Award as the ruggedly jumpy and determined university astronomy professor Dr. Mindy.

Though DiCaprio has been nominated for those seven Oscars — five for Best Actor — he has only one win. That finally came here, for The Revenant. And, quite honestly, for a role that various critics feel isn’t necessarily his best. However, his take of a real-life frontiersman, who must go to the extreme to survive, deserves serious praise. DiCaprio put his heart and dedication into the project, which is what the Academy likes. In the end, he was rewarded for an honor that was long overdue.

Often times with ensemble casts, great performances in said films get lost in the mix. Maybe that is Leo's case from The Departed. It's another Scorsese film that brilliantly shows DiCaprio’s acting depth, perhaps more so than any other movie on this list. Viewers can see for themselves, and should be able to feel, his emotional and physical pain as an undercover cop trying to take down a notorious Irish mob boss (superbly played by Jack Nicholson). DiCaprio has won awards and earned more praise for other roles during his career, but this one is truly special.

The blockbuster picture that made Leo a box-office giant and international superstar. Schmaltz factor is high with this one, but that's OK. Jack Dawson will go down as one of the most iconic and beloved characters in the history of cinema. Thanks to DiCaprio, and with a little help from Kate Winslet's Rose, the character made women fall for that type of man and made guys eager to emulate Jack's live-life-in-the-moment attitude. If Hollywood was looking for its next golden boy, DiCaprio sailed right into that spot at the right time.

As we can tell from this list, 1993 was a breakout year for DiCaprio, in terms of mainstream moviegoers' awareness of his immense talent. This coming-of-age drama paved the way for DiCaprio's first Academy Award nomination — in the Best Supporting Actor category. Leo exceptionally plays the mentally challenged younger brother of Johnny Depp’s Gilbert Grape. He didn’t win the Oscar for the role, but the door had opened, and the excellence was more than ready to flow.

DiCaprio’s working relationship with Scorsese continued with this black comedy based on stockbroker Belfort’s memoir. DiCaprio also produced the film, showing that his worth in Hollywood had grown beyond what we see on screen. Of course, his sensational portrayal of the corrupt, yet undisputedly genius, boiler-room specialist earned him and the picture Academy Award nominations. Once again, DiCaprio was not awarded the Oscar for Best Actor, but he did walk away with his second Golden Globe.

Apparently, DiCaprio's performance here was not worthy of Oscar consideration. However, he was nominated for a Golden Globe. Directed by Steven Spielberg and co-starring Tom Hanks, Catch Me If You Can is a fun film. It's DiCaprio who successfully delivers in the starring role as the young con man posing as a Pan Am airlines pilot. It’s actually pretty easy to root for Abagnale — a cool criminal and smooth operator. It also seemed that DiCaprio had a very good time making the movie. Not many can make conning banks and beautiful women with his captivating charm and persuasiveness look easy, and so damn entertaining.