On their own, Matt Damon and Leonardo DiCaprio are two Hollywood icons that can easily draw money. However, when paired together, the duo are an unstoppable force, which is why their sole collaboration remains essential viewing. Released in 2006, the near-perfect crime thriller made a big splash at the box office, and now, 20 years later, it’s once again making waves on streaming.
Damon and DiCaprio Lead a Masterpiece Crime Thriller


While Damon and DiCaprio were already huge stars by the time the mid-2000s rolled around, it took director Martin Scorsese to bring them together for what is arguably one of the best movies ever made. Hitting theaters on Oct. 6, 2006, The Departed stars DiCaprio as Billy Costigan, a troubled young Boston police officer who is recruited to go undercover inside the criminal organization of Frank Costello (Jack Nicholson). Damon plays Colin Sullivan, a Massachusetts State Police officer who has secretly been working for Costello since he was a kid.
Brought to life with the aid of Brad Pitt, who serves as a producer on the film, The Departed is about so much more than just two men on opposing sides of the law. It’s about loyalty, betrayal, and identity, as both Billy and Colin are pretending to be something they’re not. That really takes its toll on the former, as, throughout the course of the movie, we watch as he becomes increasingly more paranoid the deeper he infiltrates Costello’s organization.
Also starring Mark Wahlberg, Martin Sheen, Vera Farmiga, and Alec Baldwin, The Departed managed to gross $291 million against a budget of just $90 million. Not only did Scorsese take home the Oscar for Best Director for his efforts, but the film also won Best Picture at the 79th Academy Awards, beating the likes of Letters from Iwo Jima, The Queen, Babel, and Little Miss Sunshine. That was before the Oscars went from five to 10 Best Picture nominees in 2009.
Readily available to watch on one streaming service or another depending on the month, it’s HBO Max where DiCaprio and Damon’s crime thriller masterpiece is making the most noise this October. The Departed was added to the popular platform on Oct. 1, and the film now sits as the eighth most popular movie overall in the U.S., sandwiched in between two Halloween favorites: Friday the 13th and The Shining. However, you better act fast if you want to watch it, as The Departed is already set to depart HBO Max on Oct. 31.
‘The Departed’ Really Is a Near-Perfect Movie
As if its accolades and box office success weren’t enough to prove that The Departed is one of the best movies of all time, its Rotten Tomatoes scores offer even more evidence. Not only is it Certified Fresh with 91% from critics, but it also boasts a fantastic 94% audience rating. Called everything from “an absolute banger” to a “brilliantly tense crime thriller where nobody feels completely trustworthy,” it’s easy to see why the movie is once again a streaming smash. It’s just a shame we haven’t seen DiCaprio and Damon share the screen since.

