Thirty-one films, and five Academy Awards nominations later, Leo finally took home the Oscar last week (and we could not be more proud). We all know the saying: “If at first you don’t succeed, try again.” Well, Leo taught us that sometimes, the fifth times the charm! In the spirit of this long-awaited success, let’s reflect on all the times this beautiful man deserved an Oscar (but didn’t actually get one).
1. The Wolf of Wall Street
In 2013, Martin Scorsese brought us this three hour long masterpiece. Complete with sex, drugs, and our main man, Leo, it’s no wonder this film was a smash at the box office. We were all sad when bae didn’t win Best Actor or Best Motion Picture of the Year.
2. The Great Gatsby
This film adaptation to F. Scott Fitzgerald’s acclaimed novel had so many amazing elements: the soundtrack, the costumes, and especially the casting. They could not have picked a more appropriate Jay Gatsby than Leo.
3. Titanic
This movie won 11 Academy Awards and not a single one of them was for our boy, Leo? Tragic.
4. Revolutionary Road
Kate Winslet and Leonardo DiCaprio join forces again in this heart-wrenching performance. If you loved their dynamic in Titanic, you’ll definitely love them in this movie.
5. Shutter Island
Not your usual Leo-love story, but still fantastic! If you’re into sci-fi/action/horror/mystery films, this is the movie for you.
6. Catch Me if You Can
Can you even call yourself a real Leo fan without having seen this? (I own it on VHS.)
7. The Man in the Iron Mask
This one is an oldie but a goodie. Leo really showcases his talent here; he plays the protagonist and the villain simultaneously.
8. Romeo and Juliet
A classic Shakespearean tragedy set in 1990’s gang wars: Need I say more?
9. Django Unchained
In another one of Quentin Tarantino’s eccentric film, Leo stars as Calvin Candie, a cruel, southern plantation owner. Leo made us hate him in this role (but we still really love him).
10. Blood Diamond
Leo shows us his badass in this action-packed film about the African diamond trade.
11. The Departed
Martin Scorsese casted Leo as the lead in this thriller. AND Matt Damon as his partner? Talk about a match made in heaven.
12. Inception
The fact that Leo lost the Oscar to Jeff Bridges in 2010 is truly heartbreaking. This movie was mind blowing, and if you haven’t seen it, you must. Leo stars as a supernatural thief who has the rare ability to enter people’s dreams. Although he uses these powers for corrupt reasons, Leo can feel free to make an appearance in my dreams any time.