Suffice to say, spoilers abound below.

1. No Country For Old Men

Topping the list is this masterpiece by the Coen Brothers where our main protagonist, the guy we’re rooting for, doesn’t make it to the finish line. I don’t want to completely ruin it if you haven’t seen the film but it wonderfully encapsulates the feeling Cormac McCarthy’s novel of the same name all while consistently ramping the tension up and down. Here’s one of the tensest scenes.

2. The Usual Suspects

Bryan Singer is seemingly a fan of the bad guy getting away in the end. “The Usual Suspects” has perhaps the best ending scene reveal of just who the bad guy is as he’s getting away in cinema history.

https://www.youtube.com/watch?v=D5k73jx2mIc

3. Road to Perdition

Arguably the best role Tom Hanks has ever played in his entire career (or Jude Law), you don’t see the ending coming in “Road to Perdition” because it occurs just when you think it’s all been resolved in the most idyllic way possible, a father and son living happily in a beach cottage. In this case the bad guy comes out on top simply by preventing a happy ending.

4. Nightcrawler

Only the fantastic direction and production work prevented me from picking my tv up and throwing it out the window at the end of Nightcrawler, Jake Gyllenhaal’s creepiest, sleaziest role and well in the running for sleaziest role of all time. Here’s the scene just before the ending credits where the desire to choke Gyllenhaal’s character is at its strongest point.

https://www.youtube.com/watch?v=ZtOKLcQJXxU

5. 1984

Not only do the good guys not win but the bad guy beats everyone by corrupting love itself and revealing that the hero’s tools are actually the tools of the enemy. “Why is hate less vital than love?”

6. The Dark Knight

Batman absolutely loses while the people of Gotham absolutely win by not killing each in the ferry scene. At the end, Harvey Dent, the man Batman had seen as Gotham’s salvation, is dead at Batman’s own hand and his hope for retiring as a longed for legend is dashed. Key quote, “You have nothing to do, with all your strength.”

7. Rosemary’s Baby

Rosemary knows there’s something wrong with her baby but no one will listen. Then it turns out he’s the son of the Devil and the entire world loses. Wow, high stakes.

8. Saw (All of Them)

Really the ultimate winning bad guy, Jigsaw manages to win through six entire movies. Even when people survive, he’s getting exactly what he wants. Here’s where it all started.

https://youtu.be/dAWK9V9Hk_A?t=57s

9. 12 Monkeys

I was obsessed with this movie for a long time because of the quirkiness dreaminess it mixed in with the somewhat hard to follow apocalyptic setting involving time travel planned out by people who barely know what they’re doing. The movie itself is a circle and introduces the disconcerting notion that everything is preordained no matter what. Director Terry Gilliam was in the finest of forms here.