One of the great joys of The Departed is seeing two of Hollywood’s most charismatic stars at the top of their game, heightened by the film’s oppositional structure. Though Leonardo DiCaprio and Matt Damon are both among the most respected and popular actors working today, they have had very different careers. DiCaprio started as a child actor and eventual teen heartthrob before becoming a legitimate star for directors like Scorsese, Spielberg, Nolan and Tarantino. Damon, on the other hand, came to Hollywood a little later in life, but with a huge bang. After establishing himself as a dramatic lead he has shown a tremendous amount of range in broad comedies to big action films. The Departed came at an interesting time in both of their careers, near the start of their primes as they were stepping into superstardom. Overall, DiCaprio and Damon have been nominated for a combined eight Academy Awards for acting and each have won one statue [Damon’s win was as a screenwriter, however]. Luckily for us, many of their defining roles are available to stream on Netflix, showing their progression as actors. Here are five highlights available now:
What’s Eating Gilbert Grape [Lasse Hallström, 1993]
Though it wasn’t his first film [can’t forget Critters 3], What’s Eating Gilbert Grape was the breakout for 19-year-old Leo DiCaprio. The film stars Johnny Depp as a young man who must care for his developmentally disabled younger brother as his obese mother can’t. What seems like a morbidly depressing film is surprisingly engrossing, in part because of DiCaprio’s performance. Playing a teen with a mental disorder is a ridiculous ask—performers his age don’t often have the nuance or confidence to make the character more than lowest common denominator vocal and physical tics. Leo gives much more than that, with a lot of heart and power in the most emotional scenes. He received his first Oscar nomination [and wouldn’t receive another for 11 years], but there was no way to see the kind of star he would become.
Good Will Hunting [Gus Van Sant, 1997]
Damon’s breakout came four years later with Good Will Hunting. With screenwriting partner and BFF Ben Affleck, Damon showed off his Boston roots nine years before The Departed. He plays the title character, a janitor at M.I.T. who is discovered as a mathematical genius with a bit of an “angry young man” problem. A touching drama about identity, it is a fantastic showcase for the young actor showing off a more emotional side than how he’s typically known. The film is also known for a standout performance for Robin Williams as Will’s inspirational but troubled psychologist—a performance that won the late actor his only Academy Award. Aside from Affleck, Good Will Hunting was also the start of a cinematic partnership between Damon and director Gus Van Sant. The two would work together twice again: moody indie Gerry and less successful fracking drama Promised Land [which is also on Netflix streaming if you’re curious].
Titanic [James Cameron, 1997]
The role that turned DiCaprio into one of the biggest stars in Hollywood, his role as scrappy young Jack Dawson melted the hearts of teenage girls everywhere. Still incredibly young, Titanic uses the actor in a role he has rarely played: a romantic lead. Nowadays, whenever Leo has a love interest it is usually immensely dark, like in Revolutionary Road, Inception or Shutter Island. Jack isn’t exactly squeaky clean, but he is a much more classic romantic hero with social circumstances out of his control being the tension instead of a direct character flaw. It is far from his best performance, but it is one of his most important roles, and it is certainly fun to see him as a fresh-faced [and quite dreamy] youngster. DiCaprio scarcely worked over the next five years [The Man in the Iron Mask and The Beach the only major roles during this time] until he hooked up with Scorsese for the first time with Gangs of New York and set off the rest of his career.
Rounders [John Dahl, 1998]
Only a year after Good Will Hunting, Damon starred alongside Edward Norton in what some consider the definitive poker movie ever made, a full ten years before the cultural height of the game. Damon plays a law school student and poken enthusiast who loses his shirt to Russian mobster played deliciously by John Malkovich. Having left the poker life, Mike is sucked back in when his hustler childhood friend is released from prison. The film definitely helped establish Texas Hold’em as the preferred poker variant as its authenticity found a following among poker players. Damon is completely believable as a high level poker player, able to sell the lingo and showing competency for the mental game [knowing him as a genius in Good Will Hunter may have helped with that]. Above all, though, it makes the game cool, showing off all the rush and tension of playing. It made poker completely cinematic against the actual nature of the game. If Rounders didn’t exist, would poker have played on major sports networks in prime time?
Django Unchained [Quentin Tarantino, 2012]
Possibly DiCaprio’s best performance, his role in Django Unchained showed that the now completely entrenched actor was willing to take big chances. To say Leo chews the scenery as plantation [and slave] owner Calvin Candie is a massive understatement—more accurate to say he eats it whole. In Quentin Tarantino’s style of letting actors develop their characters over long setpiece scenes, Candie’s introduction is one of the best in the film. He’s completely despicable, without any redeeming quality, but you can’t take your eyes off of him. DiCaprio’s trademark charm is slathered on the screen in a devilishly entertaining way. Some thought this was his best chance at finally winning an Oscar, but he was passed over for a nomination against his co-star and eventual winner Christoph Waltz. No matter the lack of recognition, Calvin Candie will remain one of the most memorable performances of his career.