If you ever spent time cutting out images of your favorite teen heartthrobs in the ‘90s to tack to a corkboard in your bedroom, one guy you undoubtedly included was Leonardo DiCaprio. Leo-mania hit hard in the late ‘90s thanks to the behemoth Titanic, but Leo himself had been acting in many roles prior to the romantic disaster film. And, he’s one of the very few teen dreamboats who has managed to transition from teen star to adult star. Just look at that Bop cover above — Leo is the only one who is still a huge Hollywood mainstay.
Leonardo DiCaprio was born in 1974 in Los Angeles, and got the acting bug pretty early on, appearing on the children’s television series Romper Room at just five years old. It wouldn’t be until about 10-ish years later, though, that he finally started to get his big break with more consistent roles. Though the role that likely was his big break was on the short-lived sitcom Parenthood (based on the film of the same name), the role most people will remember as his big break was actually as a recurring character on Growing Pains from 1991-1992. From then on, Leo got consistent work in feature films, often taking on the roles of complicated characters.
Leo’s true break into stardom came, of course, when Titanic hit it huge, propelling him into leading man status in a big way. Though he was never very comfortable with being considered a heartthrob, Leo was able to use his status to transition to more hefty, adult-centric roles when he started working with Martin Scorsese on The Gangs of New York. From there, he changed from the young, hot actor, to a much more serious artist, garnering many accolades over the years until he finally won the Academy Award for Best Actor in 2016 for The Revenant.
Leo is still going strong today, with many projects in the pipeline. But acting isn’t the only thing he’s passionate about — he is also a big environmental activist. He established the Leonardo DiCaprio Foundation in 1998 to promote environmental awareness, most specifically focusing on global warming, promoting renewable energy, and preserving Earth’s biodiversity. But, that’s probably not what you’re here to read about! Below, we’ve picked some of Leo’s most memorable roles during his teen dreamboat phase, culminating in what we consider to be the final “dreamboat” movie before he took his more adult-centric turn.
Wanna check out all of our ‘90s teen dreamboats? We know you do. Click here for a complete breakdown!
Parenthood (1990-1991)
Based on the popular film of the same name, Leo starred in the short-lived television sitcom Parenthood as Garry Buckman, who was portrayed by Joaquin Phoenix in the film version. The show only lasted for 12 episodes, but featured not only Leo in one of his earliest roles, but also David Arquette and Thora Birch. Joss Whedon, who would go on to create Buffy the Vampire Slayer, was also a writer on the show.
Growing Pains (1991-1992)
For the seventh and final season of Growing Pains, Leonardo DiCaprio played the recurring character of Luke Brower, a homeless boy who is taken in by the Seaver family. His character was meant to appeal to teenage female audiences, and while maybe he did, it wasn’t enough to boost the ratings, and the show was canceled.
This Boy’s Life (1993)
Based on the memoir of the same name, Leo starred in This Boy’s Life as the titular boy, Tobias “Toby” Wolff. The true story also stars Robert DeNiro as an abusive stepfather to Toby, who shows his true colors while Toby’s mom is away.
What’s Eating Gilbert Grape (1993)
In What’s Eating Gilbert Grape, Leo stars as Arnie, the mentally handicapped younger brother to Johnny Depp’s character Gilbert. Leo actually got an Academy Award nomination for Best Supporting Actor, but lost to Tommy Lee Jones for his role in The Fugitive. Still, this film really started to put Leo on the map as a young actor to watch.
The Basketball Diaries (1995)
Based on the autobiographical novel of the same name, The Basketball Diaries was about a young man’s teenage years playing basketball while getting addicted to heroin. Leo stars as the lead character Jim Carroll who follows the typical drug story tropes of getting in over his head, trying to clean up, relapsing, and eventually finding his way back out.
The Quick and the Dead (1995)
An often overlooked film, The Quick and the Dead features an all-star cast including Sharon Stone, Gene Hackman, and Russell Crowe in addition to Leo, and was directed by Sam Raimi. Though the film had a dismal box office and mixed reviews at the time, in the years since, people have come to view it as an underrated film.
Romeo + Juliet (1996)
Based on William Shakespeare’s famous play, Baz Luhrmann’s Romeo + Juliet stars Leo as Romeo and Claire Danes as Juliet. While some modern remakes don’t use Shakespeare’s actual dialogue, this one does, and luckily, thanks to the great cast, we can easily understand what they mean! This film was just as important as Titanic in cementing Leo’s heartthrob status, in our opinion.
Marvin’s Room (1996)
In Marvin’s Room, Leo has more of a supporting role as the son of Meryl Streep’s character, who has been estranged from her family for many years. She must come back and help out, though, when her sister Bessie (played by Diane Keaton) gets leukemia and needs a bone marrow transplant. It’s definitely one of the more low-key movies of Leo’s career.
Titanic (1997)
Ah yes, the mighty beast that is/was Titanic. We probably don’t need to explain this film, but for those who don’t know or don’t remember, Leo plays Jack Dawson, a young man who wins a ticket onto the doomed ship. He falls in love with Rose, played by Kate Winslet, one of the upper class who, despite all her money, is unhappy. We still are upset over the ending, though, dang it!
The Man in the Iron Mask (1998)
In the period film The Man in the Iron Mask, Leo stars as both the title character and the villain, though the movie is really more of an ensemble film, as it also stars Jeremy Irons, John Malkovich, Gerard Depardieu, and Gabriel Byrne. The film centers on those four guys as current and former musketeers who devise a plan to replace the evil King Louie XIV with his secret identical twin brother who has been locked up with an iron mask bolted to his face so there could be no fighting over the throne. Is it the best movie in the world? No. But did I own it on VHS? You bet.
The Beach (2000)
Based on the book by Alex Garland, The Beach was directed by Danny Boyle and starred Leo as Richard, a traveler who finds a hidden and kinda mysterious beach that not many people know about. Though the film itself was only okay, the soundtrack was really good, and I may or may not have listened to it many, many times on my portable cd player.
Let us know your favorite roles of Leo’s in the comments, but first, check out some of his early commercials:
- His mother was inspired to name him Leonardo because when she was pregnant with him, she was looking at a Leonardo da Vinci painting in the Uffizi museum in Florence, Italy when he first kicked.
- He turned down the role of Anakin Skywalker in Star Wars: Episode II. Funnily enough, another of our teen dreamboats was also in the running for that role — Jonathan Jackson (read more about him here).
- In March 1998, he sued Playgirl magazine over plans to publish a fully nude picture of himself in their upcoming July issue. He eventually settled with the magazine in June of the same year.
- He was initially cast as Patrick Bateman in American Psycho, but had to drop out due to scheduling conflicts. Christian Bale eventually took on the role.
- Leo was offered the role of Dirk Diggler in Boogie Nights at the same time that he was offered the role of Jack Dawson in Titanic. After encouragement from James Cameron, he went with Titanic — the Boogie Nights role eventually went to Mark Wahlberg.
- His mother was inspired to name him Leonardo because when she was pregnant with him, she was looking at a Leonardo da Vinci painting in the Uffizi museum in Florence, Italy when he first kicked.
- He turned down the role of Anakin Skywalker in Star Wars: Episode II. Funnily enough, another of our teen dreamboats was also in the running for that role — Jonathan Jackson (read more about him here).
- In March 1998, he sued Playgirl magazine over plans to publish a fully nude picture of himself in their upcoming July issue. He eventually settled with the magazine in June of the same year.
- He was initially cast as Patrick Bateman in American Psycho, but had to drop out due to scheduling conflicts. Christian Bale eventually took on the role.
- Leo was offered the role of Dirk Diggler in Boogie Nights at the same time that he was offered the role of Jack Dawson in Titanic. After encouragement from James Cameron, he went with Titanic — the Boogie Nights role eventually went to Mark Wahlberg.
