5 Best Leonardo DiCaprio Movies of All-Time

The last spot on the list of the 5 Best Leonardo DiCaprio movies was a difficult spot to fill. There are several other movies from the actor (What's Eating Gilbert Grape, The Departed, The Aviator, etc) that arguably could be on a top 5 list. But I decided to go with The Basketball Diaries because of Leonardo DiCaprio's convincing portrayal of a drug addicted high school kid, "Jim Carroll". Based on a book by the real Jim Carroll, The Basketball Diaries was released in 1995 and received mixed reviews. Film critic Roger Ebert thought the film was too literal and that Leonardo DiCaprio was miscast. But, even if too literal, the film and the performance have vividly stuck with me for over 15 years though so I think it deserves to be on this list.

No. 4 Marvin's Room

Number four on the list of the 5 best Leonardo DiCaprio movies goes to the overlooked film Marvin's Room which co-starred Meryl Streep and Diane Keaton. Even though the story focuses more on the relationship between Meryl Streep and Diane Keaton, Leonardo DiCaprio is an anchor for the movie. Roger Ebert had this to say about the actor: "...on his good days, is one of the best young actors we have. Here he supplies the nudge the story needs to keep from reducing itself to a two-sided conversation; he is the distraction, the outside force, the reminder that life goes on and no problem, not even a long death, is forever." Outside of the acting, Marvin's Room is also one of the best dramas of all-time. If you haven't seen it, you need to.

No. 3 Titanic

Because of its titanic-sized popularity, it might be tempting to leave the movie Titanic off of a list of the 5 best movies featuring Leonardo DiCaprio. Sometimes, popularity has a way of backfiring... people get sick of the hype and the praise and feel it's even a bit uncool to like something so loved by the masses. But I will never forget seeing Titanic in the theaters and hearing a collective sigh from the girls in the audience when the actor came onscreen. Titanic is the movie that made tons of girls fall in love with the actor, Kate Winslet a star, Celine Dion a hit, and it is one of the best Hollywood blockbusters of all-time as well.

No. 2 This Boy's Life

What a movie to start off one's film career... This Boy's Life is another powerful drama which gave the young actor a chance to show off what he's capable of at a fairly young age.

No. 1 Revolutionary Road

Taking the top spot of the best Leonardo DiCaprio movies is one of the most underrated films of all-time, Revolutionary Road. The film isn't for everyone; you have to be a lover of dramas to really appreciate this story about a married couple living in the suburbs during the 1950s. But even if Revolutionary Road isn't the type of movie you typically enjoy, that doesn't take away from the fact that everything about it is just about perfect. That Leonardo DiCaprio or his co-star Kate Winslet weren't nominated and didn't win Oscars for their performances in Revolutionary Road is a shame.

Source: Ebert, Roger. The Basketball Diaries - Reviews, April 21, 1995. (rogerebert.com)