Podcast

Tuesday, October 06, 2026

What Should’ve Won That Could’ve Won: 2006

The Year: 2006
What the Nominees Were: Babel, The Departed, Letters from Iwo Jima, Little Miss Sunshine, The Queen
Other Movies That Should Have Been Considered: Ryan Fleck and Anna Boden’s Half Nelson was pretty brilliant. Over in Germany, The Lives of Others was great.
What Should’ve Won and Did Win: The Departed
How Hard Was the Decision: Very hard, because The Departed is not an all-time classic. I slightly prefer Half Nelson and Letters from Iwo Jima, but not strongly enough that I felt like I could take away Scorsese’s win. In the end, possession is nine tenths of the law.

Director: Martin Scorsese
Writer: William Monahan, based on the movie Infernal Affairs, screenplay by Alan Mak and Felix Chong
Stars: Leonardo DiCaprio, Matt Damon, Jack Nicholson, Mark Wahlberg, Martin Sheen, Ray Winstone, Vera Farmiga, Alec Baldwin
The Story: Conflicted cop Billy Costigan goes deep undercover infiltrating the operation of Boston mob boss Frank Costello, but Costello has his own infiltrator in the police, a go-getter named Colin Sullivan. Which rat will sniff out the other first, and will anyone be left alive?

Any Other Nominations or Wins: It won Picture, Director, Adapted Screenplay and Editing. It lost Supporting Actor for Wahlberg.
How It Won: I remember that it was a little shocking at the time, because reviews were not ecstatic, but Scorsese had never won and it was time to make up for past slights. Scorsese is one of the most beloved figures in Hollywood, and this movie was just good enough to get him across the finish line.

Why It Won:
  1. This is not Scorsese’s best movie (I’ve already given one to Goodfellas, and Taxi Driver and Raging Bull are certainly better than this one, but got passed over in stronger years) but it is the most fun. It’s simply a thrilling cops-n-robbers shoot-em-up. It seems like everybody had a blast making it.
  2. DiCaprio seems to have taken to heart the criticism of his terrible performance as an Irish-American in Scorsese’s earlier picture Gangs of New York and portrays the nationality much more authentically here. He talks on the DVD about the research he had to do. Damon and Wahlberg, on the other hand, are actually Southie guys and get to let that all hang out for once. Wahlberg got his only Oscar nomination and earns it, but Damon should have gotten one, too. Wahlberg says it was easy to channel the role from his childhood memories, with the only difference was that he was playing the kind of guy who used to arrest kids like him.
  3. Costigan is ordered to put his info into an envelope, but the envelope has the word Citizen misspelled so he crosses it off and writes it correctly. Well, as it turns out, this envelope changes hands many times, and it’s very important that we recognize it each time we see it, and characters who spot it briefly have to recognize it instantly. Crossing out that word was a brilliant way to do that.
  4. Costello is closely based on real life criminal Whitey Bulger, who ran crime in Southie in Boston for 20 years while secretly informing for the FBI. Amazingly, Bulger was at large when they made this (#2 on the FBI’s Most Wanted list) which makes this a rather courageous story to tell. (Bulger was eventually caught, convicted and murdered in prison in 2018.)
  5. There’s a lot of cultural appropriation going on here. Screenwriters Mak and Chong wrote a movie about their native Hong Kong, Monohan kept just the bones of that and built a new story about his native Boston Irish, and Scorsese chose to direct it because it reminded him of growing up around the Italian-American mafia in Little Italy. For this movie to come together, everybody had to trust that what they knew was universal enough to fit into someone else’s framework.
  6. There are X’s in every scene where somebody gets killed, which is a direct reference to the original version of Scarface, which did the same thing. Scorsese talks about in the extras how he couldn’t deal with the mob in the streets growing up because his asthma left him too weak to fight back, so he hid in the movie houses. The two places were equally important in giving Scorsese the abilities he would someday need.
  7. Before this movie, screenwriters were terrified of cell phones. It seemed like these magical devices would make storytelling suddenly impossible, because they could solve most problems the writers could dream up. But this movie came up with all sorts of ways that cell phones, and the primitive state of texting, could create more dramatic possibilities, not fewer. (Of course, at the time, when phones still had keypads, you could text with your phone in your pocket, something you can’t do with modern phones.)