I'm straining here, but it just so happens I watched two films about pickpockets in the last two weeks which inspired this list (and is pretty much the case with any of my Top 5 lists).
1. Sam Fuller's "Pickup On South Street" is pretty much the definitive choice for the down on his luck pickpocket who gets in over his head. Nuclear war secrets, KGB and CIA agents stalking him... all over a little reach into a jacket pocket. Fuller (ever the guy to take a tawdry subject and put a prescient spin on it), strikes the perfect balance between noir and Cold War paranoia. Richard Widmark may best be remembered for pushing an elderly woman down a staircase in her wheelchair, but for me the iconic image is his face as he goes to work on the pedestrians on a bus.
2. Robert Bresson's "Pickpocket" is long overdue for a re-watch, but I'll never forget the impact it had on me as a discovering film addict. Hearing Paul Schrader and Martin Scorsese rave about this movie in various film books highly piqued my interest. Watching any Bresson film is like an immediate film course, but "Pickpocket's" economy of images, succinct editing style and dry allegory is a marvel all unto itself. I didn't fall over later Bresson pics, but there's something really special about "Pickpocket".
3. Sparrow- itsamadmadblog fav Johnnie To's film from last year ranks in the middle of his later, more stylized genre pictures. It's a film that observes the day to day activities of a group of pick pockets, first conning each other and then later getting mixed up with an underworld boss whose passion is also stealing things. It's all choreographed in To's head-spinning mixture of tracking shots and fetishistic slow-mo. And there's a love story. And comedy. Basically, everything To is known for wrapped into an entertaining ball. His cast, including Simon Yam, Kelly Lin and Suet Lam, are back for round number 10 or so with director To behind the camera and they make it look so easy.
4. The first mumble core pickpocket movie? I think so. Josh Sadfie's erratic, neurotic little indie "The Pleasure of Being Robbed" is an oddity. Starring Eleonore Hendricks, who also co wrote the film, as a pickpocket who wanders the streets of New York (and is filmed, seemingly, by hidden cameras.... yes it's that micro budget) stealing purses, luggage (which happens to contain kittens in one haul) and eventually gravitating to grand theft auto... even though she's never driven a vehicle in her life. Not completely successful, "The Pleasure of Being Robbed" is an absorbing day in the life of an unrepentant thief who manages to exact charm and intelligence one minute before degrading into obnoxiousness and "yeas" and "umms" every other word the next. I suppose that's the best and worst of this new found thing called mumble core.
5. Not available on DVD but suddenly all over cable movie channels, Bruce Geller's early 70's film stars James Coburn as a master thief teaching two young pickpockets the laws of their trade. Full of 70's funk and style, the film never really takes off, although it does feature a decidedly downbeat ending that fits in nicely with the pessimism of 70's cinema.