Leonardo DiCaprio - My Top Picks

Rachel
Jun 10
5 min read

Consider this my formal apology to anyone who knew me between the ages of 12-16. I'm so sorry you had to sit and listen to me attempt (and succeed) to incorporate Leonardo DiCaprio into every conversation, regardless of what the topic was. I know I was annoying, but I was also unconditionally and irrevocably in love with him. Throughout those trying times - I say trying because I became extremely sad over the fact that he wasn't 22 anymore - I sat myself down and watched a good chunk of his filmography; the good and the bad. I have not rewatched almost any of these movies since, so this list is technically 14 or so year old me's top picks, but I stand by her choices.

The Basketball Diaries

Year: 1995

Director: Scott Kalvert

Starring: Leonardo DiCaprio, Mark Wahlberg, Lorraine Bracco, Ernie Hudson

Description: A teenager finds his dreams of becoming a basketball star threatened after he free falls into the harrowing world of drug addiction.

My Thoughts: I'm pretty sure I watched this expecting there to be way more basketball. Maybe a heartwarming championship game victory at the end. Nope! This is a gut wrenching film, and Leo's acting is beyond incredible. I sincerely believe he should have won an Academy Award for this performance. In my tenth grade health class we did hot seat with someone new everyday, and when it was my turn someone asked what my favorite movie was and I said this. THIS. In my health class. Luckily everyone, including my teacher, thought it was a cute basketball movie. The most interesting part about this movie is the fact that it is a true story based on the real Jim Carroll's novel with the same title. For some reason, I really couldn't tell you why, I became obsessed with the quote "Every wise ass punk on the block says it won't happen to them, but it does." Did I relate to it at all at age 14? No. I was far too young to watch this film when I did, but I really did love it and I still do.

Catch Me If You Can

Year: 2002

Director: Steven Spielberg

Starring: Leonardo DiCaprio, Tom Hanks, Christopher Walken

Description: Barely 17 yet, Frank is a skilled forger who has passed as a doctor, lawyer and pilot. FBI agent Carl becomes obsessed with tracking down the con man, who only revels in the pursuit.

My Thoughts: I've seen this one a couple times now, and it always hits. Normally I do not like long movies (thanks ADHD), but this one is so engaging it wasn't a problem for me, even at a whopping two hours and twenty minutes. Leo and Tom Hanks had great chemistry and once again his acting in this film was superb. For the most part, this one is more lighthearted than The Basketball Diaries.

Once Upon a Time... in Hollywood

Year: 2019

Director: Quentin Tarantino

Starring: Leonardo DiCaprio, Brad Pitt, Margot Robbie

Description: As Hollywood's Golden Age is winding down during the summer of 1969, television actor Rick Dalton and his stunt double Cliff Booth endeavor to achieve lasting success in Hollywood while meeting several colorful characters along the way.

My Thoughts: This was one of the first films I watched after realizing I was actually into watching movies as not just a pastime or hobby, but more of a passion. I became obsessed with true crime around the age of 11, so I was well versed in everything Manson Family by the time this film was on my screen. Seeing all of this play out but with that twist of an ending is what kick started my realization that film is the absolute best storytelling platform. I'd also like to point out how strange but cool it is that most of the actors of minor characters from this film went on to have their big breaks within the next few years. Mikey Madison, Margaret Qualley, Austin Butler (I know he was already famous but Elvis came out a few years later), Sydney Sweeney, Maya Hawke, and Victoria Pedretti.

What's Eating Gilbert Grape

Year: 1993

Director: Lasse Hallström

Starring: Leonardo DiCaprio, Johnny Depp, Darlene Cates, Juliette Lewis, Mary Steenburgen

Description: A young man in a small Midwestern town struggles to care for his mentally-disabled younger brother and morbidly obese mother while attempting to pursue his own happiness.

My Thoughts: "He's inside trying to figure out what's eating Gilbert Grape. Turns out it's a flesh-eating virus" - that one guy in the "Tuesday the 17th" episode of Psych. Again, another striking performance from Leonardo DiCaprio. Is there anything that man can't do (except date women over 25)? This is actually a tragic movie and I'm not sure why Google labels it as a comedy. It most definitely is not. I can't say much more about that without spoiling the movie, but don't expect to laugh much during this one. Johnny Depp's performance is also beautiful in this film. He encapsulates the struggles of his character so well, and paired with Leo's acting, makes for a very emotional movie.

Inception

Year: 2010

Director: Christopher Nolan

Starring: Leonardo DiCaprio, Joseph Gordon-Levitt, Cillian Murphy, Elliot Page, Tom Hardy

Description: A thief who steals corporate secrets through the use of dream-sharing technology is given the inverse task of planting an idea into the mind of a C.E.O., but his tragic past may doom the project and his team to disaster.

My Thoughts: If you like trippy movies that you need to watch more than once to fully grasp, this is the one for you. This film feels like when you stand up after laying down for awhile and you get a horrible head rush and the world is spinning out of control. The intricate concepts remind me of Interstellar which makes perfect sense considering they were directed by the same person. Inception is definitely and interesting watch with an incredible cast.

Titanic

Year: 1997

Director: James Cameron

Starring: Leonardo DiCaprio, Kate Winslet, Billy Zane, Kathy Bates

Description: Two young lovers from completely different backgrounds meet and fall in love on the ill-fated maiden voyage of the unsinkable R.M.S. Titanic.

My Thoughts: I watched this movie for the first time at a slumber party in fourth grade, and I have loved it ever since. The chemistry between Leo and Kate is insane (and it was for many years after; I said what I said). The story is so well thought out that I used to think Jack and Rose were real people. My only complaint is, again, I do not prefer long movies. In what world does any film need to be over three hours long? I do love this one, though, so it's my only exception. Oh, and Jack totally could've fit on the door.

Honorable Mentions

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Don't be fooled, this isn't all I've seen of Leonardo DiCaprio's filmography. I will say, not all of the films I've listed here would be classified as "amazing" to some people, but I loved them all when I first watched them. I may have been slightly biased, however. Take everything you just read with a grain of salt!