best film:  Matt Damon’s blue chip entries now include four (4) films that outpace the rest: Saving Private Ryan (1998) and The Talented Mr. Ripley (1999) – back to back in the late 1990s.  The Departed (2006) belongs in this company, and then Oppenheimer (2023) to give Damon even more depth here in the 2020s. Of the four (4) – it is actually on in The Talented Mr. Ripley (Damon plays the titular Tom Ripley) where Damon is given the most to work with – though he does high quality work in all of the aforementioned films.


It is intriguing to think of The Departed as a sort of update on Heat with Leonardo DiCaprio and Matt Damon in the oppositional cop and crook Robert De Niro and Al Pacino roles.


best performance:  This one is bit of a tossup as well – but this time between just two (2) options instead of four (4). The two both come from the back half of the 1990s when Matt Damon was in his twenties. First, Good Will Hunting (1997) is Damon’s big breakthrough. Archetypes exist for a reason – and though Good Will Hunting feels like it is riddled with clichés on the surface – it absolutely works. Backing up that role and film, just two years later, Damon delivers as the darkly complex Ripley in Anthony Minghella’s travelogue of a thriller –  the two make for a fine pair.


Good Will Hunting helped propel Matt Damon to stardom in 1997. At the age of just twenty-seven (27), Damon had an Oscar win (for writing, not acting) and was getting offered key roles from Anthony Minghella (fresh off The English Patient – the best picture winner in 1996) and Steven Spielberg. Damon has capitalized on the opportunity to achieve a long, storied career of great artistic success. He is well on pace to hit thirty (30) plus archiveable films.


stylistic innovations/traits:  From the beginning with Courage Under Fire (1996) – Matt Damon was ultra dedicated to his craft (he had to be checked into the hospital for strenuous physical exertion and weight loss for the role). Damon then wrote his own part (along with friend Ben Affleck) in Good Will Hunting (1997) and bet on himself as an actor – smart move. This is the Sylvester Stallone (Rocky) move – though others like Billy Bob Thornton (Sling Blade) have done it as well.  Damon has been in a staggering twenty-six (26) archiveable films over his career already (and clearly has not lost a step with a refined performance in Oppenheimer) and often puts himself in the hands of the best auteurs (see below). There is really no lull in that body of work either since his breakthrough in the late 1990s – remarkable depth and consistency. Damon is not an overly talented actor (it is fascinating to read the reviews of The Talented Mr. Ripley and see how often Jude Law was forecasted as the actor with the brighter future) but that 1997-1999 stretch is a wow – (including his two best performances, a fun Rounders film and performance, that monologue delivered to Tom Hanks in Saving Private Ryan) and then dueling with Leonardo DiCaprio in a Martin Scorsese film the caliber of The Departed.  The Bourne films feature Damon as the star of an auteur driven action franchise – an enviable feather in the cap for any actor. It helps his filmography to often be a part of sort of stunt cameos (Thor: Ragnarok, No Sudden Move) not to mention working with the prolific Steven Soderbergh in general.  That big picture resume is Damon’s best argument for being on this list since he does not have that one big blowout performance in a masterpiece. Also, even if Damon’s abilities may never let him hit the highs of the best actors of his generation – it speaks to his studious nature as an actor that he is never blown off the screen by more natural actors either (whether it be DiCaprio in The Departed, Edward Norton in Rounders or a scene with Cate Blanchett one minute and Philip Seymour Hoffman the next in The Talented Mr. Ripley). Though he is often the bridesmaid (Oppenheimer – another prime example where at least an actor or two (or more) give a better performance) –  but he should be praised and hailed for just having such a long list of such films (True Grit is another that comes to mind that should not be forgotten).


from The Talented Mr. Ripley – this may very well be Damon’s best work  – if not, it is a close second.  He is hauntingly good. The film and performance feature a wallop of an ending. Anthony Minghella brilliantly carries the audio of the Peter character (Jack Davenport) over into the next scene with Damon’s Ripley sitting there alone in a little evocative hall or mirrors… gorgeous shot.


directors worked with:  Steven Soderbergh (6), Paul Greengrass (3), Christopher Nolan (2), Ridley Scott (2), Gus Van Sant (1), Steven Spielberg (1), Anthony Minghella (1), Martin Scorsese (1), the Coen brothers (1), Kenneth Lonergan (1), Terry Gilliam (1)


top five performances:

  1. Good Will Hunting
  2. The Talented Mr. Ripley
  3. The Bourne Ultimatum
  4. The Departed
  5. Saving Private Ryan


archiveable films

1996- Courage Under Fire
1997- Good Will Hunting
1998- Rounders
1998- Saving Private Ryan
1999- The Talented Mr. Ripley
2001- Ocean’s Eleven
2004- The Bourne Supremcy
2005- Syriana
2006- The Departed
2007- Ocean’s Thirteen
2007- The Bourne Ultimatum
2009- The Informant!
2010- Green Zone
2010- True Grit
2011- Contagion
2011- Margaret
2013- Behind the Candelabra
2013- The Zero Theorem
2014- Interstellar
2015- The Martian
2017- Thor: Ragnarok
2019- Ford v. Ferrari
2021- No Sudden Move
2021- The Last Duel
2023- Air
2023-  Oppenheimer