"Pineapple Express": Depending on who you ask, "Drugs are bad!" Yes, even that plant called marijuana (most of the naysayers probably don't live in southern California, though -- or Washington, or Colorado). And there was probably never a more likable drug dealer ever to be portrayed on film than James Franco's Saul Silver, who gets tangled up with actual criminals (but "drugs are bad," so anyone who sells drugs is dangerous to society, right?) when his best customer (Seth Rogen) witnesses a murder and leaves a very particular strand of pot at the crime scene. After a massive gunfight, the pals escape with their life, and laugh about their illegal escapades over breakfast at a diner.
"Ocean's Eleven": Danny Ocean is one of the best-looking, smoothest talking and smartest criminals to ever arrange a heist -- and he gets away with it! *Commence shaking fists at screen.* But wait. It turns out, his actions do have consequences in the sequel, "Ocean's Twelve," and the criminal's crew is forced to give all the money back to the man they stole it from. But wait! They pull off another casino heist in "Ocean's Thirteen" and get away with it, again. *Resume shaking fists at screen.*
"American Gangster": Denzel Washington played real-life Harlem gangster Frank Lucas. Like Belfort, he also seized the opportunity to cash in on crime, but instead of selling worthless penny stocks, he sold a cheap, yet potent brand of heroin. In the end, Lucas agreed to work with the authorities to reduce his prison sentence, and helped an honest cop convict three quarters of the New York DEA -- you know, kinda like how Belfort sold out his entire brokerage firm. Lucas served fifteen years in prison, and is shown re-entering society with nothing but a second chance. Belfort went to prison and lost all his money, too, but he was smart enough to write a book while he was in the slammer.
"The Usual Suspects": The greatest trick the devil ever pulled was convincing the world he didn't exist. The same applies to criminals smart enough to invent other criminals to take the fall for their actions.
"Catch Me If You Can": Jordan Belfort isn't DiCaprio's first turn as a criminal -- it's just his sleaziest. Back in 2002, DiCaprio portrayed a very charming teenager named Frank Abagnale who had forged checks and faked occupations to steal millions of dollars before turning 19. After the FBI finally caught up with him, like it did to Belfort, Abagnale also got a second chance at making an honest living by working with the federal agency to catch other con artists cashing fake checks.
"The Godfather": The mob is bad. They kill people, and operate above the law. Yet, each installment of Francis Ford Coppola's epic crime trilogy earned a number of Oscar nominations, with Part 1 and 2 winning several. And don't try to act like you're not rooting for Michael Corleone to save his family's criminal empire and crush his opponents.
"Scarface": Tony Montana, like Jordan Belfort, wanted to live the American dream (and snort lots of cocaine) at all costs, and that's exactly what he did -- even if it meant going out in a glorious hail of gunfire and taking as many other crooks with him as he could. The Brian De Palma film, starring Al Pacino as a Cuban kingpin instead of an Italian Godfather, was initially met with criticism for its excessive violence and vulgar language. Today, many consider it a cinematic classic, and the title gangster is as cool as ever.
"Mad Money": Good ol' American values suggest crime doesn't pay, but things worked out just swell for Diane Keaton, Queen Latifah and Katie Holmes in this 2008 crime comedy about three Federal Reserve employees who steal a large stash of cash that is about to be destroyed. In the end, the gals get caught, but are let off the hook in court if they just pay their taxes. Fortunately, one of them was smart enough to stash more of the stolen money in the basement of a friend's bar.
"The Sopranos": Okay, it's not a movie, but fans of this HBO crime drama tuned in on a regular basis to watch New Jersey mob boss Tony Soprano rule his criminal empire, and kill anybody who threatened it. Did he end up paying the ultimate price for his lifetime of sin after the screen cut to black at the end of the series finale? We'll never truly know.
Martin Scorsese's filmography, in general: "Taxi Driver," "Mean Streets," "Boxcar Bertha," "Raging Bull," "The King of Comedy," "Goodfellas," "Casino," "Gangs of New York" and "The Departed" are all centered around bad people doing bad things to get something they want in life. Some of them paid for their sins with their lives, others went to prison, and some -- like deranged "King of Comedy" Rupert Pupkin (Robert De Niro) -- wouldn't have been successful without committing those sins.