Leonardo DiCaprio Through the Years: Photos 

From Titanic to Inception and beyond! Leonardo DiCaprio is one of Hollywood’s finest performers — but he had to wait over two decades before taking home his first Academy Award. 

While the actor was nominated for his first Oscar in 2000 for his role in What’s Eating Gilbert Grape, he ultimately lost out to The Fugitive’s Tommy Lee Jones. DiCaprio went on to star in endless other critically acclaimed films such as Titanic, The Aviator, Catch Me If You Can, The Departed and more — receiving a total of six nominations for Hollywood’s biggest honor — but didn’t take home his own statue until 2016 for his role as Hugh Glass in The Revenant. 

“I am so grateful to the Academy for their recognition of this film. Making The Revenant was one of the most rewarding and collaborative experiences of my life,” DiCaprio gushed on stage during his acceptance speech. “None of this would have been possible without [director] Alejandro [González Iñárritu]’s talent, vision and determination. Our dedicated crew also deserves to share in this moment. Together, they have created a truly unique cinematic experience. Congratulations to all of my fellow nominees this season. Thank you to the Academy.”

Despite his eventual win, many have criticized the Academy for DiCaprio’s endless snubs over the years. The California native, for his part, has admitted to being disappointed in lack of recognition before. 

“The truth of the matter is that I’ve been in situations before where I’ve thought films or performances, either mine or others, should be nominated more,” he said during the Andrew Marr Show in January 2016. However, he has also clarified that accolades are not why he commits himself to the work. 

“I think anyone appreciates these types of things, for sure, of course — you know, to be recognized by your peers. I know it’s a cliché, but the truth is it’s ultimately not why you do these films,” he said during an episode of the Today show in 2016. “You do them because if you love the art form — and cinema to me is the great modern art form — you can look back one day and say, ‘I did that piece of work, and I gave it everything I could while I was there.’ And if you have enough of those later on in life, you’re a happy artist.” 

Critic and peer approval may not be why he loves acting, but DiCaprio has certainly been recognized by other prestigious awards outside of his Oscar losses. He’s nabbed a total of 54 wins and over 150 nominations throughout his career, including three Golden Globes, a BAFTA and a SAG award, making him one of the most revered actors in cinematic history. 

While DiCaprio has given his all to his craft, he also enjoyed the benefits of being a Hollywood heartthrob. The Blood Diamond actor has been romantically linked to a string of female celebrities over the years, often facing criticism for his flings with younger women.

Despite his many dalliances, that doesn’t mean the Golden Globe winner hasn’t had his fair share of serious relationships. DiCaprio began dating Gisele Bündchen in late 1999 and the twosome were on and off for six years before calling it quits for good in 2005. They even attended the 77th Academy Awards together, where the Growing Pains alum was nominated for Best Actor for his performance in The Aviator. 

While the duo ultimately split due to the supermodel feeling increasingly “alone” in her life, she has little regret about their time together. 

“Everyone who crosses our path is a teacher; they come into our lives to show us something about ourselves,” the Brazil native told People in September 2018. “And I think that’s what he was. What is good versus bad? I honor him for what he was.”

While Bündchen later moved on with Tom Brady — though the pair divorced in 2022 — DiCaprio, for his part, found love again with Bar Refaeli, whom he dated for nearly six years before their 2011 split. He’s also been linked to Blake Lively and Nina Agdal, whom he dated for less than a year in 2016. He later fell for Camila Morrone and the former couple were together for four years before their summer 2022 breakup. In 2023, he made headlines after sparking romance speculation with Gigi Hadid. 

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Scroll down to take a look at Leonardo DiCaprio through the years: