Leonardo DiCaprio has gone through numerous transformations in his many successful decades as an actor. From being the baby-faced charmer who captured our hearts in Titanic to winning an Oscar for his portrayal of a rugged outdoorsman in The Revenant, DiCaprio always seems to be evolving. Here, we revisit every Leo incarnation since his introduction to the spotlight in 1989.

1989©Getty Images

In 1989, DiCaprio was just starting out in Hollywood with a small role as Glen in two episodes of the television show The New Lassie.

1990©Getty Images

DiCaprio landed a small role on the show The Outsiders in 1990, and was then cast as Garry Buckman on the short-lived show Parenthood. That scored him nominations for two Young Artist Awards.

1991©Fotos International – Getty Images

DiCaprio posed on the set of the popular television series Growing Pains, where he played the role of Luke Brower.

1992©Ron Galella, Ltd. – Getty Images

Looking like the definition of an early ’90s teen, DiCaprio was pictured at the MTV Rock N’ Jock B-Ball Pediatric AIDS Foundation.

1993©Getty Images

This was the year DiCaprio’s career really picked up. First, he starred opposite Robert DeNiro in This Boy’s Life, and then he played a career-defining role as the mentally handicapped brother of Johnny Depp in What’s Eating Gilbert Grape.

1994©Jim Smeal – Getty Images

DiCaprio made his first appearance at the Golden Globes in January of 1994, looking adorably fresh-faced.

1995©Catherine McGann – Getty Images

DiCaprio starred in three films in 1995, the most well-known being The Basketball Diaries alongside Mark Wahlberg and Lorraine Bracco.

1996©Frank Trapper – Getty Images

This was the year DiCaprio cemented his status as a true teen heartthrob, thanks to his role in Baz Luhrmann’s Romeo + Juliet. He showed up to the premiere looking slightly rumpled with then-girlfriend Kristin Zang on his arm.

1997©SGranitz – Getty Images

DiCaprio attended the Los Angeles premiere of Titanic in 1997, a role that would define his career and cause every viewer to sob publicly in a movie theater.

1998©Getty Images

In 1998, DiCaprio showed up to the 55th Annual Golden Globe Awards in a tux and slightly more tamed spiky hair.

1999©Getty Images

This was the first year DiCaprio wasn’t starring in a newly released movie or show. Instead, he spent most of the year filming The Beach.

2000©Getty Images

DiCaprio gave a sweet smirk as he posed for photos at the Hollywood premiere of The Beach at Mann Chinese Theatre.

2001©Scott Gries – Getty Images

In 2001, the actor made an appearance at The Concert for New York City to benefit the victims of 9/11.

2002©Getty Images

DiCaprio secured his leading man status with two big roles in 2002: one in Martin Scorsese’s Gangs of New York, the other as Frank Abagnale Jr. in Catch Me If You Can.

2003©Tony Barson Archive – Getty Images

DiCaprio looked bronzed and rocked facial hair at the Gangs of New York premiere in Paris, France.

2004©Gregg DeGuire – Getty Images

Leo has never kept his dedication to the environment out of the spotlight. Here, he attended the Dedication of NRDC’s (Natural Resources Defense Council) New David Family Environmental Action Center and the Leonardo DiCaprio e-Activism Zone, encouraging visitors to learn more about environmental issues.

2005©Getty Images

In 2005, DiCaprio won his first Golden Globe award for Best Actor in a Leading Role: Drama for his role as Howard Hughes in The Aviator.

2006©Fotos International – Getty Images

DiCaprio starred in two major motion pictures in 2005: The Departed and Blood Diamond. Both scored him Golden Globe nominations for Best Actor in a Motion Picture Drama, and his Blood Diamond role got him a Best Actor nom at the Academy Awards.

2007©Getty Images

This year, DiCaprio didn’t appear in any new releases, but he did spend much of early 2007 flaunting a slicked-back look on the awards show circuit.

2008©Fotos International – Getty Images

2008 saw DiCaprio reunite with his Titanic co-star and dear friend, Kate Winslet, in Revolutionary Road, a role that got him another Best Actor nod at the Golden Globes.

2009©Getty Images

DiCaprio posed at the 20th anniversary of the Palm Springs International Film Festival Awards Gala, presented by Cartier.

2010©Steve Granitz – Getty Images

2010 was another huge year for Leo, with leading roles in two mind-bending movies, Shutter Island and Inception.

2011©Dave M. Benett – Getty Images

DiCaprio spoke at the Cinema For Peace inaugural Cannes dinner, which honored Sean Penn for his charity work in Haiti.

2012©Getty Images

In 2012, DiCaprio took on an intense role in Quentin Tarantino’s Django Unchained, and proved that a classic tux never goes out of style.

2013©George Pimentel – Getty Images

DiCaprio attended the 70th Annual Golden Globe Awards, where he was nominated for Best Supporting Actor in a Motion Picture for Django Unchained.

2014©Getty Images

In 2014, DiCaprio spent a lot of time at awards shows for his role in The Wolf Of Wall Street. He was nominated for Best Actor for the Academy Awards and the Golden Globes, as well as a slew of others.

2015©Jacopo Raule – Getty Images

DiCaprio made an appearance at the Giorgio Armani 40th Anniversary Silos Opening and Cocktail Reception in Milan, Italy, looking much hairier than usual.

2016©Getty Images

This was a huge year for DiCaprio: he finally took home Best Actor at the Academy Awards for his performance in The Revenant.

2017©Eddy Chen – Getty Images

Things quieted down for DiCaprio after the success of The Revenant, but he kept busy, serving as a very handsome announcer at the 89th Academy Awards.

2018©Isaac Brekken – Getty Images

DiCaprio attended the CinemaCon 2018 Gala Opening Night Event, rocking a casual look just after flaunting 3-D glasses as part of an incognito Coachella ensemble.

2019©Stephane Cardinale – Corbis – Getty Images

DiCaprio collaborated with Quentin Tarantino for the second time in the comedy-drama Once Upon a Time In Hollywood, which tells several nonlinear stories about the end of the Golden Age of Hollywood and charts the Tate-Labianca murders carried out by the Manson Family. For his performance as Rick Dalton, DiCaprio was nominated for his sixth Academy Award.

2020©Kevork Djansezian – Getty Images

DiCaprio speaks at the 72nd Directors Guild of America Awards, which honored excellent achievements in directing in 2019, including, among others, the WWI drama film 1917, the HBO miniseries Chernobyl, and Andrea Arnold’s debut feature American Honey. We’d be seated if DiCaprio ever tried to give directing a spin.

2021©Dimitrios Kambouris – Getty Images

After DiCaprio filmed the apocalyptic satire Don’t Look Up in late 2020, he attended the world premiere in New York City in the winter of 2021. The film had a heavy-hitting cast, which included Jennifer Lawrence, Meryl Streep, Jonah Hill, and Cate Blanchett.

2022©Gisela Schober – Getty Images

DiCaprio rocked a casual look for the amfAR Cannes Gala 2022, making a Yankees cap feel gala-appropriate.

2023©Samir Hussein – Getty Images

DiCaprio returned to Cannes in a huge way for the world premiere of Killers of the Flower Moon—his latest collaboration with Martin Scorsese. He looked snazzy in a Dior suit and black button-up with no tie.