10. "The Lookout" (2007) – Directed by Scott Frank
Chris Pratt (played by Joseph Gordon-Levitt, not the "Guardians" guy), was once a high-school hockey star. Fast-forward four years after a tragic accident, and our guy's got a bum leg and a faulty memory, making even the simplest tasks a challenge. Life's tough for Chris, but he's doing his best, holding down a job as a nighttime janitor at a bank.
Enter Gary Spargo (Matthew Goode), oozing charm and bad intentions. He hatches a plan to rob the bank, and guess who's central to the scheme? Our Chris, of course.
9. "Brick" (2005) – Directed by Rian Johnson
Brendan Frye (also Joseph Gordon-Levitt) is a high school loner who receives a panicked phone call from his ex-girlfriend, Emily (Emilie de Ravin), pleading for help. When she turns up dead, the stage is set for a classic detective story, except it's a high school kid doing the sleuthing. Brendan goes full gumshoe, infiltrating cliques that could give any mob family a run for their money.
There's the upper-crust drama queen, the seductive femme fatale, the drug-peddling Pin (Lukas Haas) in his mom's basement – each character more vivid than the last.
8. "Running Scared" (2006) – Directed by Wayne Kramer
Paul Walker steps out of the fast cars and into the fire in this one. He plays Joey Gazelle, a low-level mobster with a simple job: dispose of the guns used in mob hits. But when a neighbor kid, Oleg (Cameron Bright), swipes a piece tied to a cop killing and shoots his abusive stepdad, all hell breaks loose. Joey's world spirals as he chases Oleg through some seriously sketchy parts of town, trying to clean up the mess before the cops or the mob get wise.
You've got sadistic pimps, corrupt cops, and a hockey game that's more like a gladiator match.
7. "In Bruges" (2008) – Directed by Martin McDonagh
"In Bruges" gives us Ray (Colin Farrell) and Ken (Brendan Gleeson), two Irish hitmen cooling their heels in Bruges, Belgium, after a job goes pear-shaped. Ray is antsy and guilt-ridden, while Ken is more like your uncle who's content feeding ducks and sightseeing.
They're awaiting orders from their boss, Harry (Ralph Fiennes), who has a strict moral code that'd have philosophers scratching their heads. While Ken takes in the medieval city, Ray stumbles into romance and local film sets, messing things up as only he can.
6. "A History of Violence" (2005) – Directed by David Cronenberg
Tom Stall (Viggo Mortensen) is living the dream in small-town Indiana with a lovely wife Edie (Maria Bello) and two kids. He's a regular Joe running a diner, but when he foils a robbery in a fashion that'd make action heroes tip their hats, Tom's heroics grab the media's attention.
Cue the entrance of some shady figures from Philly, led by the scar-faced Carl Fogarty (Ed Harris), who insists Tom is someone else entirely – a mobster with a past that's all kinds of dark. What unfolds is less a whodunit and more a "who-is-it," as Tom's identity – and his family's safety – comes under threat.
5. "Gone Baby Gone" (2007) – Directed by Ben Affleck
Set the scene in the gritty streets of Boston where private investigators Patrick Kenzie (Casey Affleck) and Angie Gennaro (Michelle Monaghan) are roped into the desperate search for a missing girl, Amanda McCready.
As they dig through the city's underbelly, they're not just trailing clues but crossing paths with some hard-nosed characters like the weary Detective Remy Bressant (Ed Harris) and the morally ambiguous Captain Jack Doyle (Morgan Freeman).
4. "Kiss Kiss Bang Bang" (2005) – Directed by Shane Black
Harry Lockhart (Robert Downey Jr.) is a thief-turned-actor by sheer fluke, who's thrust into a Hollywood murder mystery. He's paired with private eye Perry van Shrike (Val Kilmer), dubbed "Gay Perry" for reasons that'll be clear as crystal when you meet him.
This duo bumbles through a series of misadventures and misunderstandings. As Harry tries to channel his inner detective for a movie role, the bodies start piling up for real.
3. "Eastern Promises" (2007) – Directed by David Cronenberg
After "A History of Violence", Cronenberg isn't done with the crime genre. This time, the story is set in the London underworld of Russian mobsters. Naomi Watts plays Anna, a midwife who's out of her depth when she tries to trace the family of a baby left orphaned by a teenager's death during childbirth. Viggo Mortensen's Nikolai is a driver for the mob.
As Anna's path intersects with Nikolai's, the grim reality of sex trafficking, loyalty, and the savage struggle for power in the Vory v Zakone (Russian criminal brotherhood) comes into stark relief.
2. "The Salton Sea" (2002) – Directed by D.J. Caruso
Val Kilmer plays Danny Parker, a man whose life is as shattered as the glass of the meth pipe he smokes. He's an informant for two corrupt cops (Anthony LaPaglia and Doug Hutchison) and dives deep into the drug-fueled lifestyle of the California underworld. But Danny's not just another junkie; he's a jazz trumpeter with a past that haunts him like a relentless ghost.
The more you learn about what drives him, the more you realize his every move is part of a larger, more devastating score.
1. "Layer Cake" (2004) – Directed by Matthew Vaughn
Before Daniel Craig donned the tux as Bond, he was cooking up something else entirely in "Layer Cake." He's a nameless cocaine distributor who's all about the business, not the gangster lifestyle. He's got a plan to retire early, but we all know how plans go in the crime world.
The 'Layer Cake' refers to the social strata of the criminal hierarchy, and Craig's character gets a taste of every layer when his boss, Jimmy Price (Kenneth Cranham), asks him to find the missing daughter of an associate.