By Jessica Herndon
8:15am PST, Nov 8, 2018
After his parents divorced when he was a year old, Leonardo DiCaprio grew up in Los Angeles, mostly with his mother, Irmelin, in an area near Hollywood Boulevard known for prostitution. But his mom drove him across town daily after he earned a scholarship to University Elementary School in the residential neighborhood of Westwood, which introduced him to the elite side of the city. His acting career started as a pre-teen when he appeared in commercials, but in 1991, he landed his first movie part in the sci-fi horror-comedy "Critters 3." That same year, he won a role on the TV show "Growing Pains" (pictured).
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In 1993 when Leonardo DiCaprio was 14, he starred in the stirring drama "This Boy's Life" opposite Robert De Niro, who played his abusive stepfather. When Leo was 9 years old, his own father, George, took him to see De Niro in "Midnight Run" and told him if he wanted to be an actor, he needed to know what a great actor was.
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Following "This Boy's Life," Leonardo DiCaprio was offered a hefty check for a role in Disney's "Hocus Pocus." Instead, he held out for the part of an autistic teen opposite Johnny Depp and Juliette Lewis in "What's Eating Gilbert Grape." Leo earned his first Oscar nomination at 19 for his incredible performance.
Leonardo DiCaprio stretched his talent again, making Hollywood take notice when he dynamically played poet and drug addict Jim Carroll in the 1995 biopic "The Basketball Diaries." But it wasn't only credibility he was gaining. During this time, the hottie had become a regular in popular teen mags like Bop and Tiger Beat.
In 1996, Leonardo DiCaprio starred in Baz Luhrmann's "Romeo + Juliet" opposite Claire Danes and really began to secure his place as a star — and as a swoon-worthy leading man.
At the premiere of "Romeo + Juliet," Leonardo DiCaprio made one of the first of many appearances with a model by his side, revealing his tendency to date beauties like Bridget Hall, Naomi Campbell and Kristen Zang (pictured) — all of whom he wooed early in his career.
Leonardo DiCaprio became a bona fide superstar and heartthrob in 1997 with the release of megahit "Titanic," which also starred Kate Winslet. To this day, James Cameron's romantic disaster movie remains the second-highest grossing film ever, just behind "Avatar," with $2.2 billion.
In 2002, Leonardo DiCaprio starred opposite Cameron Diaz in Martin Scorsese's "Gangs of New York." This was the first of many films Leo would make with Martin. After the crime drama premiered in New York, a flirty Leo and Cameron — who was dating Jared Leto at the time — spawned rumors that a romance was brewing. But the reports were never confirmed.
Two years later, Leonardo DiCaprio starred as Howard Hughes in "The Aviator." The 2004 biopic was nominated for 11 Academy Awards including best picture and won Leo his first Golden Globe for best actor.
After dating supermodels like Helena Christensen, Bijou Phillips, Amber Valletta and Eva Herzigova in the '90s, Leonardo DiCaprio continued his model-dating reign, kicking off the 21st century with Gisele Bundchen on his arm. The two, seen here attending the 77th Annual Academy Awards in Los Angeles on Feb. 27, 2005, dated on and off from 2000 to 2005.
By 2008, Leonardo DiCaprio and Kate Winslet had re-teamed for the drama "Revolutionary Road," in which they played a married couple living in the suburbs in the mid-1950s. Both delivered compelling performances, and both were nominated for Golden Globes. But only Kate received a best actress nod from the Academy when Oscar nominations were announced.
From 2005 to 2009 and then again in 2010 and 2011, Leonardo DiCaprio was romantically linked to Israeli model Bar Refaeli. What began as a fling with the then-20-year-old model grew into a full-fledged relationship, which led many to believe Leo had found The One. He and Bar reunited in 2010 following a six-month break, during which time Leo hooked up with Russian model Anne Vyalitsyna (also known as Adam Levine's ex Anne V).
In 2011, Leonardo DiCaprio, best bud Tobey Maguire, Ben Affleck and Matt Damon made headlines after Tobey faced a lawsuit in connection with a multimillion-dollar gambling ring involving underground poker games that Leo, Ben and Matt also participated in. Tobey was sued and eventually forced to pay back $80,000 because he'd won more than $300,000 from a hedge fund manager who'd embezzled millions from investors to play in the games — which required a $100,000 buy-in. (In a case of art imitating life, Jessica Chastain later played the woman who ran the poker ring in the 2017 biopic "Molly's Game.")
In 2011, Leonardo DiCaprio took a break from dating models to date actress Blake Lively, who is now married to Ryan Reynolds. The pair had quite the jet-setting romance as they packed on the PDA from Italy to Australia. They were first seen in May 2011 getting cozy on Steven Spielberg's yacht in Monte Carlo during the Cannes Film Festival. By late August that same year, Blake was flying from the States to Sydney where Leo was filming "The Great Gatsby." Leo reportedly loved the fact that Blake was a homemaker who'd always bake for him. But by October, the fire between them had fizzled.
After his split from Blake Lively, Leonardo DiCaprio was back to dating models, starting with Erin Heatherton, to whom he was linked from 2011 to 2012. It was also around this time that Leo debuted a bushy beard — a look he'd often return to between movies.
Leonardo DiCaprio, Carey Mulligan and Tobey Maguire starred in Baz Luhrmann's 2013 spectacle "The Great Gatsby." The film received lackluster reviews, but critics dug Leo's captivating performance. They're all seen here at the movie's Cannes Film Festival premiere.
Leonardo DiCaprio was enjoying the high life while flyboarding during a vacation in Ibiza, Spain, on Aug. 7, 2013. Another perk of being an A-lister? Hanging out on the world's fifth-largest yacht. While attending the World Cup in June 2014, Leo and 20 pals borrowed the 482-foot $700-million Topaz — which features a jacuzzi, swimming pool, fitness center and double helicopter landing pads — for a Brazilian getaway.
In 2013, Leonardo DiCaprio starred in the deliciously lewd "The Wolf of Wall Street," the fifth film he's made with Martin Scorsese, and was nominated for two Oscars — one for acting and another for producing the film. Unfortunately, he went home empty-handed: Leo lost the best actor trophy to Matthew McConaughey, who scooped it for his performance in "Dallas Buyers Club." Meanwhile, the best picture prize went to "12 Years a Slave." Leo and Marty are seen here at the 2014 National Board of Review Awards Gala that January.
Leonardo DiCaprio might have gone home empty-handed at the Oscars for his work on "The Wolf of Wall Street," but he had the best date around! Leo brought mom Irmelin Indenbirken to the 86th Academy Awards on March 2, 2014. So cute!
Leonardo DiCaprio is also a do-gooder, especially when it comes to environmental activism. Here he is with U.N. Secretary General Ban Ki-moon after being named a United Nations Messenger of Peace during a ceremony at U.N. headquarters in New York City on Sept. 20, 2014. It's a post he's using to speak out about climate change.
Leonardo DiCaprio relaxed on the beach in Miami on July 19, 2014. He loves the beach so much that he even bought an island off the coast of Belize — which features an eco-friendly resort and homes — in April 2015.
Politically speaking, 2015 was a big year for Leonardo DiCaprio, who really wants to save the planet. He spoke at the Global Citizen Festival in New York City's Central Park on Sept. 26, 2015, where he told the crowd, "The cause of our environment and the fight for the world's poor are inherently linked. The planet can no longer wait."
Leonardo DiCaprio was honored with the Actors Inspiration Award for his onscreen career and dedication to philanthropy during the Screen Actors Guild Foundation's 30th anniversary celebration in Los Angeles on Nov. 5, 2015.
Leonardo DiCaprio maintained his bushy beard for his award-winning film, Alejandro G. Iñárritu's "The Revenant," which hit theaters on Dec. 25, 2015. He played explorer Hugh Glass, a man who's seeking vengeance after being attacked by a bear and left for dead by members of his hunting team.
In 2016, Leonardo DiCaprio finally won an Oscar after being nominated six times! The A-list actor, who took home the prize for his performance in "The Revenant," made sure to speak on climate change during his acceptance speech. "Making 'The Revenant' was about man's relationship to the natural world, the world that we collectively felt in 2015 as the hottest year in reported history — our production needed to move to the southern tip of this planet just to be able to find snow," Leo said. "Climate change is real. It is happening right now. It's the most urgent threat facing our entire species and we need to work collectively together and stop procrastinating."
After his Academy Award win, Leonardo DiCaprio briefly focused on producing. He executive produced "Catching the Sun," a documentary on the growth of the solar power industry; "The Ivory Game," a documentary that examines the ivory trade; "Live by Night," a movie about a notorious gangster; and "Before the Flood," a documentary on climate change that he also narrated and hosted. All four films were released in 2016.
Leonardo DiCaprio made headlines in early 2018 when he began dating model Camila Morrone — who is nearly 23 years his junior. Leo and the then-20-year-old model were first spotted together in late 2017 after reportedly being introduced by Al Pacino, who previously dated Camila's mother.
Leonardo DiCaprio also produced "Delirium," a psychological horror film, in 2018. The movie, which stars Topher Grace, Patricia Clarkson, Callan Mulvey and Genesis Rodriguez, tells the story of a man who inherits a possibly haunted mansion from his wealthy deceased father after being released from a mental institution. Leo is seen here speaking at the CinemaCon 2018 Gala Opening Night in Vegas in April 2018, a month before "Delirium" hit theaters.
In the summer of 2018, Leonardo DiCaprio started filming the period crime-drama "Once Upon a Time in Los Angeles" opposite Brad Pitt and Margot Robbie. The Quentin Tarantino film, which takes place during the time of the Manson Family murders, will be released in July 2019.
