Five Times Leo DiCaprio Played Bad Guys Instead of Sweet Heartthrobs
It seems that the usually good guy Leo has no problem playing the much more controversial characters.
Leonardo DiCaprio has had an amazing career over the years, bringing to life countless memorable characters with his excellent performances.
From Romeo in Romeo + Juliet (1996) to Dr. Randall Mindy in Don't Look Up (2021), he mostly sticks to playing positive characters.
But every once in a while, he steps away from his usual good guy archetype to play much less positive roles, sometimes even outright villains, and still manages to make them memorable or even sympathetic.
Here are five of our favorite ones.
Brandon Darrow – Celebrity (1998)
In an American comedy-drama film written and directed by Woody Allen, Leo played the role of spoiled Hollywood star Brandon Darrow.
The destructive, abusive, and impulsive actor embodies the worst traits of movie celebrities and draws the film's protagonist, Lee Simon, portrayed by Kenneth Branagh, into the dark world of Hollywood's underbelly.
Frank Abagnale – Catch Me If You Can (2002)
Although DiCaprio's brilliant portrayal of a real-life con man has made viewers root for his character, Frank is by no means a hero.
He defrauds people and makes millions in the process, but his superior intellect allows him to escape justice time and time again.
J. Edgar Hoover – J. Edgar (2011)
In Clint Eastwood's biographical drama, Leonardo portrays the first director of the Federal Bureau of Investigation.
Although he is portrayed as a true patriot who cares about his country, he must make some morally questionable decisions that tarnish his supposedly positive image, including an unsuccessful attempt to blackmail Martin Luther King Jr.
Calvin J. Candie – Django Unchained (2012)
As the charming yet diabolical owner of the Candyland plantation, Leo's charismatic performance was the cherry on top of an already great western from legendary director Quentin Tarantino, making Calvin one of the most memorable movie villains of the past decade.
Jordan Belfort – The Wolf of Wall Street (2013)
Yet another portrayal of a real-life criminal made sympathetic by DiCaprio's fantastic acting skills.
Jordan made a fortune through illegal financial machinations on the stock market, and Leo's portrayal of this slippery but brilliant drug addict and alcoholic is a guilty pleasure to watch from start to finish.
