Danny Ocean – Ocean’s Eleven
While he does have a knack for landing himself in jail, Danny Ocean’s life seems pretty enjoyable outside of three-to-six month trips to prison. He spends most of his free time planning elaborate heists with his close friends. Who hasn’t dreamed of doing that at least once in their life?
Ocean’s Eleven focuses mainly on the robbing of three Vegas casinos, so we don’t see Danny’s personal life in the actual movie, but there’s enough evidence to suggest most people wouldn’t mind living like him. We’ve already covered the heists, but Danny is also extremely composed (allowing him to be in control of any situation) and has the smarts to outwit his foes – as evident by him winning back his ex-wife from Terry Benedict. Plus, having a share of a $160 million jackpot doesn’t sound so bad either.
What differentiates Danny from other movie criminals is that at his core, he’s a thief with a heart of gold. Unlike certain mobsters and gangsters, he is not corrupt or power hungry and only wants his ex-wife to love him back. At the conclusion of the film, Danny even takes the fall for his entire crew – going to jail while the rest of the team enjoys their share of the heist. Reaching that level of selflessness is something we would like to achieve, especially since most movie criminals are greedy people who are only out for themselves.
Frank Abagnale, Jr. – Catch Me if You Can
The Wolf of Wall Street isn’t the first time Leonardo DiCaprio played a real-life criminal. Frank Abagnale, Jr. may not have made $49 million the year he turned 26, but his accomplishments were extremely impressive. Running away from home as a teenager, Frank spends a number of years posing as an airline pilot, doctor, and lawyer, conning his way to millions of his own all before he turned 21.
While few would sign up for the emotional trauma Frank went through after his parents’ divorce, one can see how useful skills of forgery can be (particularly when it’s difficult to catch you). At a time when most of us are sitting through high school math, Frank is flying with Pan Am stewardesses. Instead of writing college application essays, he’s partying-on at Riverside Apartments in Atlanta. Suave, charming, and highly intelligent, Frank possesses a lot of qualities men want and his brief lifestyle of driving Aston Martins and wooing beautiful women seems fun.
Frank was eventually caught and sent to prison, but he even found a way to get out of that. Serving four years of a twelve-year sentence, Frank gets a job – ironically enough – working in the FBI’s check fraud department, finishing out his punishment as a “free” man. As the film’s closing credits notes, Frank designs checks for banks and Fortune 500 companies, legally earning a large amount of money annually. So even his fall ended up being beneficial.