Heist Movie Bracket: Vote on the Elite 8

By Jake Skubish

Welcome to the Break-In Bracket, where we are voting for the best heist movie since 1975 in honor of the 45th anniversary of Dog Day Afternoon. Voting buttons for each matchup are below. You can follow along with the progress of the bracket here.

The Clay Region

(1) Reservoir Dogs vs. (2) Ocean’s Eleven

The Matchup: The two “group of super cool dudes” heist movies finally face off. Reservoir Dogs’ brand is a little grimier, and a lot more violent. The men don’t bother to learn each others’ real names; they’re coming together strictly to pull off a job, which is why the relationship that develops between Mr. White and Mr. Orange is so emotionally compelling. But the fact of the matter is, the movie focuses on the aftermath of the crime, and it doesn’t really matter whether they pulled a heist or some other misdeed entirely. Ocean’s Eleven uses the heist as a conduit for economic justice and personal revenge, and the crew has fun with each other while pulling it off. I have to go with Ocean’s Eleven.

The Gondorff Region

(1) Heat vs. (2) Inside Man

The Matchup: Two heist movies where the thief and the police officer develop a personal relationship, and a begrudging sort of respect. The Pacino-De Niro dynamic in Heat is awesome, but like most Michael Mann films, the plotting is also overstuffed; this movie does not need to be three hours long. Meanwhile, Inside Man unfurls perfectly. Revelations about each character’s motivations continue at a steady pace, and it caps off with a two surprises at the end, one about the mechanics of the heist and one about the motivation for the heist, that take the movie to another level. I’m going with Inside Man.

The Bonnet Region

(1) The Usual Suspects vs. (6) National Treasure

The Matchup: National Treasure is playing the same role that 13 Going on 30 did in the rom-com bracket: the half-decent nostalgia pick that makes it just a little too far in the tournament. It’s a fun time, but come on. The Usual Suspects is ingenious, and though Spacey’s performance gets all the attention, Gabriel Byrne and Benicio Del Toro are also incredible. It’s time to end the Cinderella run and let the real masterpiece move on.

The Sonny Region

(2) Jackie Brown vs. (4) Fantastic Mr. Fox

The Matchup: Two movies that I’m really excited have made it this far! These are two undervalued gems that I did not think would emerge out of this field, but they absolutely deserve to. As much as I love Fantastic Mr. Fox, though, this is as far as I think it should go. We already have a better George Clooney caper remaining, anyway. Jackie Brown may be the most emotionally resonant Tarantino movie, and the mechanics of the robbery are unlike any other heist movie. Jackie Brown is my pick.