The Wire: The best television series of all time, and also coincidentally a sprawling crime story epic told from the point of view of the cops and the criminals alike. Produced and written by journalists, a former police detective, and a number of notable crime novelists, its a pretty stunning indictment of the "War on Drugs" and its consequences on the lives of everybody it touches. While the focus shifts away from street level crime at times to discuss city politics and the media, it still keeps an eye on the corner kids, the drug kingpins, the Baltimore PD, and the bureaucracies they answer to. Full of characters drawn from real life composites, all of them many times more interesting and multi-dimensional than the gangstas and cops you get out of shows like CSI or any hundred action movies, it also provides a no-to-low bullshit accounting of what investigating or committing crime is actually like. McNulty is a particularly interesting character as he's an archetypal Maverick Cop that never fires his gun once in anger but still manages to be a pain in the ass to everybody he meets. I simply can't recommend it enough, even if you prefer Dirty Harry and Lethal Weapon to the real deal.
Heat: A modern classic, its another "big" story of cops and robbers, this time set in 90's L.A. Arguably Michael Mann's best film to date and chockful of scenes, characters, and scenarios you could rip off in your 10K game. The heist shootout is rightfully noted by a lot of people as a particular gem in the pantheon of Hollywood gun battles - and it'd ironically inspire the horrific real world North Hollywood shootout in 1997. Stylish and thoughtful, its the kind of action movie you don't feel dumber for having watched.
Miami Vice: The updated film version of Michael Mann's quintessentially '80s cop show isn't a classic by any means, but that doesn't keep it from being worth seeing as a 10K reference. You get lots of scenes of tough guys (and girls) being stoic and slick, fancy drug kingpin houses, outrageously expensive cars, boats, and planes, and a corker of a climactic shoot out that may excuse the fact that its kind of unnecessary and the main plot is just going through the motions. Watching white supremacist drug thugs get blown apart is just FUN, damn it.
The Killer: John Woo's high-octane melodrama about a super-cool assassin seeking redemption is simultaneously absurd and sublime, particularly when things reach a head in a church gun battle that has to be seen to be believed. Don't look for subtlety or realism here, just pure cinematic overdrive grounded by great performances by the main actors (especially Chow Yun Fat as the title character), grandly tragic gestures, and a lot of artful violence. While Woo has produced many (bad) imitators in contemporary action cinema, you really owe it to yourself to see this movie if you haven't yet. Its like the French film La Samourai but with kick-ass action and more heart.
Hard Boiled: Another John Woo action masterpiece, but one that is more than a little inspired by American action blockbusters like Die Hard and Lethal Weapon. Its about a hard boiled supercop, a renegade undercover cop, and about five thousand disposable Triad goons armed with automatic weapons. The tone is lighter and more playful than the Killer, but its not quite in the realm of self-parody found in Once a Thief. There's some sequences in the climactic act that play like a action fan's fever dream, with continuous shots lasting minutes as the heroes stylishly run-and-gun down dozens of gangster drones. Woo would come over to America after this film and make some not-quite-as-good (Face/Off) to just-plain-bad (Paycheck) action flicks for the big studios, but this was his last hurrah of '90s Hong Kong bloodshed.
Memories of Murder: This Korean film is a quirky look at a serial killing spree that happened in South Korea in the '80s. The cops are anything but bulletproof or infallible, the murderer is a perplexing enigma, and the scenes are chilling in their depiction of pointless acts of violence. Its like Se7en without the smarm of that film or its improbably perfect mastermind.
Zodiac: Speaking of Se7en, David Fincher totally redeemed himself for that movie to my mind with this depiction of the real world Zodiac Killer who scared the beejezus out of 1970's San Francisco. It follows the obsessive investigations of a SFPD cop (played by Mark Ruffalo) and a political cartoonist (that Gyllenhal..gyller...you know the name...guy) as they try to track down the murderer. The picnic murder scene is one of the most terrifying I've ever seen on film - and its accomplished without flashy editing or superhuman acts of mad genius/depravity. Don't expect any car chases, but when it comes to showing detective work at its best/worst, its endlessly fascinating.
The Dark Knight: Look, I know its a Batman movie, but its Batman done right as far as I'm concerned. For all the explosions, you've got a big crime movie that just happens to feature a guy dressing up as a bat as its vigilante hero. There's a great cast, great dialog, and some genuinely interesting and unsettling questions about law enforcement, vigilantism, terrorism, and notions of good and evil. While it was a surprise to movie goers used to camp and dutch angles (damn you Schumacher!!!), for Bat-nerds like me, it was totally what we'd been waiting for since, well, 1939. AND its still 10K fodder if you take away the cape and costume.
The Sopranos: You know, I realize Goodfellas set a kind of template for this show, but I think I like the Sopranos more than Scorcese's movie. Maybe its the fact its a serialized, longer and more in-depth story, or maybe the funny stuff is funnier, or maybe its commentary on the American dream and its relationship to crime is more pointed - but whatever the case, this HBO milestone is much more satisfying. That includes the perplexing ending. I think my favorite episode is "College" from the first season; on the one hand, its about Tony seeing his daughter growing up and that universal coming-of-age experience. On the other hand, its about Tony tracking down and throttling a dirty rat with his bare hands. Great stuff, and sort of the antithesis of the romantic view of La Cosa Nostra we've gotten used to.
The Godfather Trilogy: Speaking of the romanticized Mafia, here it is, in all its lurid glory. Its really a morality play that happens to make being a mobster look totally awesome, what with its sprawling dynastic story, the terrific A-list cast, the sumptuous cinematography, and a lot of unforgettable scenes. Even if it has nothing to do with real organized crime, its a great depiction of what it should be like. I even liked the third movie, despite the fact Coppola miscast his daughter (who'd go on to be a great director, herself) in a major role and that its a bit too on-the-nose when it comes to wrapping things up.
Branded to Kill: This is a batshit insane hallucinatory avante garde movie - that also happens to be about a Yakuza hitman. Its simultaneously a parody of all those poe faced Yakuza potboilers that came out of Japan in the '60s...and a poe faced Yakuza potboiler itself. The film was SO crazy that it got the director (Seijun Suzuki) blacklisted for over a decade, but its now hailed as a visionary masterpiece. If you think Tarantino is the bee's knees, I'd suggest grabbing this movie and seeing how you really make a postmodernist absurd crime film.
Shoot the Piano Player: Speaking of postmodernist absurd crime movies, this is a French neo-noir by Truffaut about a piano player who gets mixed up with some gangsters and a femme fatale. Its very arty and inescapably French, but unlike a lot of French new wave movies it actually manages to be entertaining. Watch for the scene where a dim-witted gangster swears on his mother with unintended comic consequences.
The Killing: Nifty heist film directed by Stanley Kubrick. Features a lot of oddball crooks, a guy with a home-made automatic shotgun, and the typically detached-but-calculated Kubrick touch.
The Asphalt Jungle: Another heist film, this time from John "I Directed The God Damned Maltese Falcon" Houston. Its got a great cast of 50's character actors (including a very young Marilyn Monroe) and a nifty set of subplots for each as the criminals pull of the job only to succumb to ironic fates. I really dig Sterling Hayden's laconic "muscle" character in this; tough on the outside, soft on the inside, and one of the few members of the gang with any sense of honor.
The Taking of Pelham 1,2,3: This is not the remake, but the original '70s film starring Walter Matthau as a hardboiled...transportation cop. You don't get much grittier than 1970's New York, and while the movie often has an unexpected comic tone in depicting the reaction of New Yorkers to a subway hijacking, there's also a pretty great pre-Die Hard cat-and-mouse between Matthau and Robert Shaw's calculating mastermind Mr. Blue (Tarantino stole the name gimmick in Reservoir Dogs from this movie). Matthau did a lot of good '70s crime films, actually; the Laughing Detective with Bruce Dern was also pretty cool.
The Driver: Walter Hill's movie about a superb getaway driver (Ryan O'Neal, before we found out what a creep he is) who is pursued by an obsessed cop (Bruce Dern). Lean and mean in that '70s crime movie fashion, its mainly an excuse for some great car chases, including a climactic one that subverts convention by being really, really slow. Trust me, it works. Great visual reference for 10K if/when you get into your car in pursuit or trying to escape from the fuzz.
The French Connection: I'm really obligated to put this here, but not because its overrated. Its just that good, people. See it.