Happy Tuesday, dear readers! Each week, we’ll rank the top 10 films in a specific category. While we aim to tie these lists to big releases, that won’t always be the case. Our goal? For you to enjoy, share your own lists, and join in on a lively, friendly debate. This is an interactive space to build community here at The Contending.
No fancy intros, no long essays – just a category and a list. Sound good?
With Leonardo DiCaprio’s latest film, One Battle After Another, hitting theaters this week, it’s the perfect time to reflect on his extraordinary career. DiCaprio has transformed from a charismatic young talent into one of Hollywood’s most compelling actors, known for his fearless immersion into complex, often flawed characters. Whether he’s portraying historical figures, antiheroes, or tortured souls, his performances are often intense and always authentic, blending emotional depth with technical precision.
DiCaprio has a long track record of collaborating with visionary directors like Martin Scorsese, Quentin Tarantino, and Christopher Nolan. One Battle After Another marks his first collaboration with acclaimed director Paul Thomas Anderson, a pairing that has been long anticipated since DiCaprio passed on a role in PTA’s Boogie Nights early in his career.
Over the years, DiCaprio has garnered six Academy Award nominations for his acting performances, starting with Best Supporting Actor for What’s Eating Gilbert Grape in 1994, followed by Best Actor nods for The Aviator (2005), Blood Diamond (2007), The Wolf of Wall Street (2014), The Revenant (2016), and Once Upon a Time in Hollywood (2020). He finally took home the Oscar for Best Actor for his grueling role in Alejandro González Iñárritu’s The Revenant. While I won’t see One Battle After Another until Thursday, early buzz suggests his performance is poised to join the ranks of his ten best.
Let’s get to Leonardo DiCaprio’s ten best performances heading into this exciting week!

10. Catch Me If You Can (Frank Abagnale Jr., 2002)

9. Inception (Dom Cobb, 2010)

8. Django Unchained (Calvin Candie, 2012)

7. Revolutionary Road (Frank Wheeler, 2008)

6. The Aviator (Howard Hughes, 2004)

5. The Departed (Billy Costigan, 2006)

4. What’s Eating Gilbert Grape (Arnie Grape, 1993)

3. Once Upon a Time… in Hollywood (Rick Dalton, 2019)

2. The Revenant (Hugh Glass, 2015)

1. The Wolf of Wall Street (Jordan Belfort, 2013)






