Entertainment Movies Drama Movies Leonardo DiCaprio Turns 50! See the Best Photos of the Hollywood Heartthrob Over the Years The Oscar winner celebrates his 50th birthday on Nov. 11 By Grace Gavilanes Grace Gavilanes Grace Gavilanes is a former associate editor at PEOPLE. She left PEOPLE in 2018. People Editorial Guidelines and Brendan Le Brendan Le Brendan Le is an Editorial Assistant at PEOPLE with three years of experience working as an editor and writer. People Editorial Guidelines Updated on November 11, 2024 08:49AM EST Leonardo DiCaprio in 1994. Photo: Alex Berliner/BEI/Shutterstock Happy birthday, Leonardo DiCaprio! The Oscar-winning actor turns 50 years old on Nov. 11, 2024. In his decades in the industry — dating back to his years on the 1980s sitcom Growing Pains — he's grown up in front of the cameras, achieving leading man status at a young age before transitioning to the ultimate heartthrob in Titanic, and now an award-winning actor. As DiCaprio celebrates a milestone half-century birthday (with a star-studded party, of course) take a look at photos of the actor over the years, from 15 to 50. 01 of 21 Oh Boy Leonardo DiCaprio in 1989. Darlene Hammond/Getty Images Looking fresh-faced as ever, 15-year-old Leonardo DiCaprio gave a half-smile as he posed for a pic in 1989. 02 of 21 TV Star Leonardo DiCaprio on 'Growing Pains'. Warner Brothers Television/Fotos International/Courtesy of Getty Images Before making a splash on the big screen, DiCaprio starred on Growing Pains as a teen, playing little brother Ben on the hit TV series. 03 of 21 Hello, Handsome Leonardo DiCaprio in 1993. Rose Hartman/Archive Photos/Getty Images DiCaprio established himself early as an A-list teen dreamboat — no one pulled off that floppy '90s do quite so well. 04 of 21 Hanging Out Leonardo DiCaprio and Johnny Depp. Ron Galella, Ltd./WireImage Pictured here with What's Eating Gilbert Grape costar Johnny Depp in 1993, DiCaprio attended an event for their film — which garnered the young actor critical acclaim and his first Oscar nod. 05 of 21 Close Connection Leonardo DiCaprio and Bridget Hall in 1994. The LIFE Picture Collection/Shutterstock Rumors of his first romance were with model Bridget Hall. Though neither ever confirmed a relationship, they were spotted cozying up in 1994. 06 of 21 Film Friends Leonardo DiCaprio and Elijah Wood in 1994. Charbonneau/BEI/BEI/Shutterstock The rising star headed to the Oscars Governors Ball in 1994, posing alongside fellow actor Elijah Wood. 07 of 21 20 Something Leonardo DiCaprio in 1995. Walter McBride/Corbis via Getty Soon after turning 20, DiCaprio hit the ground running with his film career. 08 of 21 Momma's Boy Leonardo DiCaprio and his mom. Richard Corkery/NY Daily News Archive via Getty Images Known to be close to his family, DiCaprio has regularly invited his mom Irmelin to red carpet events and film afterparties — like this instance in 1996, when she accompanied her son to a Total Eclipse event. 09 of 21 Young Love Leonardo DiCaprio with girlfriend Kristen Zangin October 1996. Ron Galella Collection via Getty For the Romeo + Juliet premiere, DiCaprio brought model and then-girlfriend Kristen Zeng as a date. 10 of 21 Come Together Leonardo DiCaprio and Claire Danes in 1996. Steve Granitz/WireImage In 1996, DiCaprio starred alongside fellow Hollywood heavyweight Claire Danes in Romeo + Juliet. The film launched the swoon-worthy actor into super-stardom. 11 of 21 O Romeo Leonardo DiCaprio in 'Romeo and Juliet' (1996). 20th Century Fox/ Everett It's easy to see why Juliet fell head-over-heels for DiCaprio's Romeo. 12 of 21 Heart Will Go On and On Leonardo DiCaprio and Kate Winslet in 'Titanic' (1997). 20th Century Fox/ Everett The next year, James Cameron's epic Titanic cemented DiCaprio as a generational star and sent him from stardom into the stratosphere. 13 of 21 Partner in Crime Leonardo DiCaprio and Kate Winslet in 1998. HAL GARB/AFP/Getty Images DiCaprio and his Titanic costar Kate Winslet — pictured here at the 1998 Golden Globes — have remained close through the years. The actor even walked his friend down the aisle at her 2012 wedding. 14 of 21 Serious Business Leonardo DiCaprio in 'The Man in the Iron Mask' (1998). United Artists/Getty Images Back to work! The actor sported a pensive expression while filming scenes for 1998's The Man in the Iron Mask. 15 of 21 Life's a Beach Leonardo DiCaprio in 'The Beach' (2000). 20th Century-Fox/Getty Images Especially when looking at pics of early 2000s Leo filming The Beach. 16 of 21 Ocean Blue Eyes Leonardo DiCaprio in November 2004. Vera Anderson/WireImage Entering the new millennium, DiCaprio continued his run of success with Catch Me If You Can, The Aviator, The Departed and Inception. 17 of 21 Attached at the Hip Leonardo DiCaprio and girlfriend Gisele Bündchen in February 2005. Frank Micelotta/Getty He brought then-girlfriend Gisele Bündchen as his date to the Oscars in 2005 when he was nominated for Best Actor. 18 of 21 Awe for the Ball Leonardo DiCaprio and Bar Refaeli in January 2010. Noel Vasquez/Getty Leonardo DiCaprio had an on-and-off relationship with Israeli model Bar Refaeli for six years, and the couple loved spending their time courtside. 19 of 21 Mr. Gatsby Leonardo DiCaprio as Jay Gatsby in 'The Great Gatsby' (2013). Bazmark Films/Warner Bros/Kobal/Shutterstock In 2013, DiCaprio reminded everyone why they first fell in love with him, working with Romeo + Juliet director Baz Luhrmann on The Great Gatsby. The actor delivered a charming and grand performance as the titular Gatsby. 20 of 21 Oscar Date Leonardo DiCaprio and Camila Morrone in February 2020. ARTURO HOLMES via Getty Although they arrived separately, Leo and his then-girlfriend Camila Morrone sat next to each other at the 2020 Academy Awards. 21 of 21 Screen Dream Sansho Scott/BFA.com/Shutterstock Yes, Leonardo DiCaprio is in this picture! To bring it back full circle for his 50th birthday, squint to see the little icon on the back of his girlfriend Vittoria Ceretti's phone (seen backstage at the Victoria's Secret fashion show): It's a photo of her boyfriend from his Growing Pains days. Close