Why Leonardo DiCaprio Makes Playing a Bad Guy Look So Good

"Wolf of Wall Street" wasn't his first time playing a con man.

ByABC News

February 26, 2014, 1:13 PM

This film image released by Paramount Pictures shows Leonardo DiCaprio as Jordan Belfort in a scene from "The Wolf of Wall Street."
Mary Cybulski/Paramount Pictures/AP Photo

Feb. 26, 2014 -- In "The Wolf of Wall Street," Leonardo DiCaprio plays Jordan Belfort, a wealthy stockbroker who comes from humble beginnings, only to end up on the wrong side of the law and come out the other side seemingly a changed man.

It's a role that has earned him an Oscar nod.

Sound familiar?

Well it should, because this Oscar-nominated actor, 39, took on a very similar role a decade earlier in "Catch Me If You Can." He played Frank Abagnale Jr., who was just a kid when he became a con man and eventually forged checks into the millions, only to be caught by the FBI.

So why does DiCaprio make being bad look so good? Here are some other similarities from the two films. If this whole acting thing doesn't work out, DiCaprio sure has proven he can charm with the best of them.

Leonardo DiCaprio with airline stewardess surrounding him in a scene from the film 'Catch Me If You Can', 2002.

In both movies, DiCaprio starts off an honest guy, just trying to get by.

In "Catch Me," he's actually in high school when his parents go through a rough divorce and he runs away from home. When his money runs out, his character is forced to start forging checks to survive. Then the fun begins.

In "Wolf," Belfort heads to Wall Street and goes to work for an honest firm. When he's laid off, then he's forced to start selling questionable penny stocks.

Also in both movies, DiCaprio makes the big bucks. In one, he ends up becoming one of the biggest forgers of checks in the world, eventually fleeing to France to escape the FBI. In the other he basically becomes a billionaire by selling people crappy investments under the guise of a reliable firm.

PHOTO: Margot Robbie arrives at the 19th Annual Critics' Choice Movie Awards, Jan. 16, 2014 in Santa Monica, Calif. | Amy Adams arrives at the premiere of "The Muppets" at El Capitan Theatre, Nov. 12, 2011 in Los Angeles, Calif. — Margot Robbie arrives at the 19th Annual Critics' Choice Movie Awards, Jan. 16, 2014 in Santa Monica, Calif. | Amy Adams arrives at the premiere of "The Muppets" at El Capitan Theatre, Nov. 12, 2011 in Los Angeles, Calif.

His co-stars Margot Robbie in "Wolf" and Amy Adams in "Catch Me" are widely considered two of the most beautiful actresses in Hollywood. Guess what, he gets to marry them both in the films.

DiCaprio takes things to another level with the ladies in "Wolf," but don't get it twisted, Abagnale didn't need any help in the womanizing department either. Nice work boys.

Kyle Chandler attends the "The Wolf Of Wall Street" premiere at Ziegfeld Theater, Dec. 17, 2013 in New York City. | Tom Hanks attends the 20th Annual Screen Actors Guild Awards at The Shrine Auditorium, Jan. 18, 2014 in Los Angeles, Calif.

Whether it's Kyle Chandler or Tom Hanks chasing you down and trying to arrest you, both of those guys play characters you want to avoid at all costs.

Hanks eventually helps out DiCaprio's character in "Catch Me," by getting Abagnale out of jail to be a consultant for the FBI, but "Forrest Gump" could certainly track down criminals with the best of them.

Going to jail is tough. But both movies end with glimmers of hope for DiCaprio's characters. Abagnale gets to work alongside Hanks at the FBI and eventually creates unforgeable checks, putting his skills to good use.

As for Belfort, he wrote the memoir that inspire DiCaprio's Oscar-nominated performance, among other books penned by the former stockbroker.

Make sure to tune in March 2 to ABC to see if DiCaprio's latest role as con man could earn him an Academy Award.