Some audiences might have first spotted Matt Damon during a notable dinner scene in Donald Petrie's hit 1988 drama "Mystic Pizza." Thereafter, Damon turned up as an extra in "Field of Dreams" and as one of the many handsome students in the 1992 boarding school thriller "School Ties," both of them with his longtime friend and collaborator Ben Affleck. Damon went on to score some considerable screen time in Edward Zwick's "Courage Under Fire" before delivering his first lead performance in 1997 in Francis Ford Coppola's "The Rainmaker." That same year, Damon and Affleck became acclaimed Academy darlings for writing and starring in Gus Van Sant's "Good Will Hunting." The pair won Oscars for their screenplay and have both been major Hollywood players since.

Damon, having gained the clout to be picky and the fame to be noticed, thereafter became attracted to projects by established directors. After having alreayd worked with Coppola and Van Sant, Damon -- in the years that immediately followed -- appeared in "Saving Private Ryan," directed by Steven Spielberg, "Dogma," directed by Kevin Smith, "The Talented Mr. Ripley," directed by Anthony Minghella, "The Legend of Bagger Vance," directed by Robert Redford, "Titan A.E.," directed by Don Bluth, and "The Departed," directed by Martin Scorsese.

Damon also continued to work with Van Sant while also becoming a regular player for Steven Soderbergh, Paul Greengrass, and George Clooney. He even appeared in two Terry Gilliam movies and two Ridley Scott movies. The man likes working with legends.

As it so happens, he also likes to watch films directed by legends. In 2021, Damon was interviewed by Rotten Tomatoes and the outlet, naturally, asked him to list his five favorite movies. Three of them, it so happens, were made by directors he had worked with before.