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.

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

1974
The Wolf of Wall Street star was born on November 11, 1974, in Los Angeles, California, and is the only child of Irmelin and George DiCaprio. While his parents divorced when he was only 12 months old, they moved into twin cottages in the neighborhood of Echo Park to coparent their son together.

1990s
Leo got his start by landing roles in Parenthood, The Boy’s Life and Growing Pains. In 1993, he starred in What’s Eating Gilbert Grape opposite Johnny Depp, earning his first Oscar nomination at just 20 years old.

1995
The Shutter Island star skyrocketed to heartthrob status after his role in Baz Luhrmann’s classic rendition of Romeo + Juliet.

1997
Leo’s iconic portrayal of Jack Dawson in James Cameron’s Titanic — opposite Kate Winslet — catapulted him to worldwide fame. The movie went on to win 11 Oscars and broke the record for the most profitable film of all time.

2000
Leo began dating Bündchen. The twosome attended the 2005 Oscars together, where the J. Edgar actor was nominated for his second Academy Award for his role in The Aviator. The duo split later that year.

2002
After starring in critically acclaimed films like 2000’s The Beach and 2002’s Gangs of New York — his first collaboration of many with director Martin Scorsese — Leo played a con man in Steven Spielberg’s Catch Me if You Can.

2005
After his breakup with Bündchen, Leo began dating Refaeili. They called it quits in 2011 after nearly six years together.

2006
The actor nabbed his third Oscar nomination for 2006’s Blood Diamond. That same year, he starred in The Departed alongside Jack Nicholson — which earned Scorsese his first Academy Award for Best Director.

2010 to 2011
Leo had the biggest box office opening of his career with Inception. He also sparked a romance with Lively. He and the Gossip Girl alum dated for a year before their split in 2011.

2012
The Don’t Look Up Star played his first villain in Quentin Tarantino’s Django Unchained.

2016
After starring in box office hits The Wolf of Wall Street and The Great Gatsby in 2013, Leo took home his first Oscar for 2016’s The Revenant. That same year, he began dating Agdal. The pair were together for over a year before calling it quits for good.

2017
The Virunga star was first linked to Morrone in 2017.

2019
Leo took a three-year break from acting before returning to the big screen for Once Upon a Time … in Hollywood.

2022 to 2023
After four years of dating, Leo and Morrone called it quits in August 2022. A source exclusively told Us Weekly at the time that the pair were “very close” but had been apart for a while due to traveling.

Following their breakup, the Man in the Iron Mask actor was linked to Hadid in September 2022. An insider told Us at the time that the twosome were “very into each other” and wanted to “see where things go.”

After Us confirmed in February 2023 that the pair had gone their separate ways due to being at “different points inter lives,” reconciliation rumors swirled one month later when they were spotted together at a handful of events.