leo dicaprio
Cast member Leonardo DiCaprio poses at the premiere of ''Inception'' at the Grauman's Chinese theatre in Hollywood, California July 13, 2010 Reuters/ Mario Anzuoni

Leonardo DiCaprio has played many roles throughout his career in Hollywood, which garnered him fame and millions of cash. He has been nominated for “Best Actor” at the Academy Awards three times; but the ultimate prize has remained elusive through the years.

He has established himself as one of the biggest stars in the world by showing his talents and flexibility when playing unique characters. Here are five Leonardo DiCaprio movie roles where he should have won “Best Actor.”

1. Catch Me If You Can (2002)

Leonardo took on the role of Frank Abagnale Jr. and had to show a balance between being a kid who fulfilled adult dreams and the dark side of being a con artist. He was more than convincing when playing the roles of an airline pilot, doctor, lawyer and FBI agent, among others.

2. The Departed (2006)

The gangster drama had an all-star cast including Jack Nicholson, Mark Wahlberg, Alec Baldwin and Matt Damon among others and was directed by Martin Scorsese. The film rated 91 percent on RottenTomatoes. Leonardo played the role of an undercover cop who attempts to infiltrate organized crime syndicates.

3. Inception (2010)

One of Leonardo DiCaprio’s more unique roles is playing an “extractor,” described as a person who performs corporate espionage through subconscious efforts. The film is a sci-fi thriller with Leo putting you at the edge of your seat throughout.

4. The Aviator (2004)

Leo played the role of billionaire and flyer Howard Hughes. He was very good in taking on the character of a rich playboy who loved planes and films. He showed his acting skills by presenting how the billionaire suffered from obsessive-compulsive disorder.

5. The Wolf of Wall Street (2013)

The film was the most recent opportunity for Leonardo to bag the “Best Actor” award. He played the role of Wall Street stockbroker Jordan Belfort who gets involved in a pump and dump scam. The Guardian reported that many fans believed that DiCaprio deserved to win but in the end, the trophy went to Matthew McConaughey.

Leonardo DiCaprio was nominated for his roles on “The Aviator” and “Blood Diamond,” too; but lost. His fans remain optimistic that he will get the prestigious Oscar award someday.