best film:   Leo may be lacking that Goodfellas or Blade Runner top one, two, three of the decade level film – but there is no shame in having Inception, The Revenant or even possibly Once Upon a time in Hollywood as your best film. The group of films a step or half-step down includes Aviator, The Departed, and Django Unchained. And there are no cameos or small parts among those six (6) films. The quietest of the six (6) may be in Christopher Nolan’s mind-bending Inception – but with closer study, DiCaprio’s work there as the steady hand at the helm (sort of acting as a Nolan surrogate with the world-making and maneuvering it all) gets better with each repeat viewing.


best performance:  The Revenant edges out a half-dozen others by a hair. Leo again does not have Daniel Day-Lewis in There Will Be Blood (that is no insult, maybe only five or six actors do) but the delta between number two here (The Aviator) and number ten (perhaps This Boy’s Life or Catch Me If You Can) is not all that great. He is outstanding as a Bogart anti-hero type in Blood Diamond and that performance is even farther down the list. In The Revenant, Leo is front and center for Iñárritu’s torture chamber of pain against a Malick-like picturesque backdrop (but with camera movement like from Mikhail Kalatozov or Bela Tarr). It is a physical performance (and a great pairing with Inception as that performance is almost entirely verbal) that reaches a level of authenticity that should be unattainable from any actor who has been the biggest movie star (or one of) in the world since 1997.


The Revenant – DiCaprio’s best? Yes – and it different than most of his work.  It is physical instead of verbal, but his weathered face is a brilliant canvas – pained, resolute.  DiCaprio is aided by Iñárritu’s camera – these are actor friendly close-ups of those glassy blue eyes. The dialogue has  lines like “I ain’t afraid to die, I’ve done it already”. It is more Steve McQueen, Clint Eastwood, Robert Redford in Jeremiah Johnson-style than Al Pacino in Dog Day Afternoon or something. He crawls for a lot of it like he did in that comic virtuoso quaalude scene in Wolf of Wall Street. DiCaprio’s dedication to the role is admirable but always in service of character and story and the brutality of the world of the film.


stylistic innovations/traits: Leonardo DiCaprio now has twenty (20) archiveable films with plenty of room in front of him if he chooses to keep working (he has worked less and less in recent years – including just three (3) films in the nine (9) years from 2014 and 2022). Still, DiCaprio is the youngest actor so far on the list – yet despite that – it is really the depth of both high quality films and performances that are his main strength for the purposes of this list. Leo’s had a eye opening 1993 with both What’s Eating Gilbert Grape (alongside Johnny Depp) and This Boy’s Life (dueling with Robert De Niro). Titanic in 1997 made him a global celebrity. He seemed to use that stardom and power to rededicate himself to doing quality work in 2002 by choosing to work with both Martin Scorsese (Gangs of New York) and Steven Spielberg (Catch Me If You Can). Since The Aviator in 2004, DiCaprio has been pretty consistently regarded as the best actor on the planet (Tony Leung right there and Daniel Day-Lewis of course when he decides to come out of retirement and make a film). He has six Oscar nominations (including a win for The Revenant).


Leo as Rick Dalton in 2019’s Once Upon a Time in Hollywood – Leo gets big actor-friendly showcase moments like the whiskey sour trailer scene and the “great f*cking note” close-up (after acting brilliantly as Rick Dalton in the show within the movie) – all of this is wrapped in an an interconnected-narrative history-being-rewritten-again Tarantino masterpiece.


directors worked with: Martin Scorsese (5), Baz Luhrmann (2), Quentin Tarantino (2), James Cameron (1), Woody Allen (1), Steven Spielberg (1), Sam Mendes (1), Christopher Nolan (1), Alejandro González Iñárritu (1).  There is no point in lamenting that DiCaprio/Scorsese will never be De Niro/Scorsese. But there are no misfires in those five (5) films together – not by a long stretch. And The Aviator and The Departed, especially, are up there with the very best films of their respective years – the evidence for this is right there on screen even if they do not touch Taxi Driver or Raging Bull. On top of that, the collaborations with Tarantino, Iñárritu, and Nolan were clearly artistic successes.


Leo did not completely land his first collaboration with Scorsese in Gangs of New York (2002). He would lose that sort of acting battle against Day-Lewis (but redeem himself by out-acting Jack Nicholson in The Departed in 2006).  It feels like it was 2004 and The Aviator when the paradigm shifted for good and those who teased him for been a teen heart throb from Titanic (not a film or performance worthy of any warranted ridicule) had to permanently shut up. DiCaprio’s Texan vibrato voice as Howard Hughes is perfect – clearly studied.


top five performances:

  1. The Revenant
  2. The Aviator
  3. The Departed
  4. Once Upon a Time in Hollywood
  5. Inception  


Leo’s work in The Departed  is both showy and genuine – such a wonderfully open or unguarded performance. This type of complex character and performance is so rare in a genre film.


archiveable films

1993- This Boy’s Life
1993- What’s Eating Gilbert Grape
1995- The Quick and the Dead
1996- Romeo & Juliet
1997- Titanic
1998- Celebrity
2002- Catch Me If You Can
2002- The Gangs of New York
2004- The Aviator
2006- Blood Diamond
2006- The Departed
2008- Revolutionary Road
2010- Inception
2010- Shutter Island
2012- Django Unchained
2013- The Great Gatsby
2013- The Wolf of Wall Street
2015- The Revenant
2019- Once Upon a Time in Hollywood
2021- Don’t Look Up