So it’s that time of the year again; the time when the Academy Awards night rolls around and friends sit round a pub table to discuss why Leonardo DiCaprio hasn’t won one yet. Nominated for Best Performance by an Actor in a Leading Role his character, Hugh Glass in The Revenant might just be his ticket to finally taking home an Oscar. Although Leo has already been nominated a couple of times it always seems to slip out of his fingers. Whatever the result of the 88th Academy Awards may be, here are our five picks of times that Leo deserved to win the award long before he was fighting bears and Tom Hardy in the harsh cold of the 1820s American wilderness.

What’s Eating Gilbert Grape
Let’s do this chronologically; his first ever Academy Awards nomination was for his role as Gilbert Grape’s younger brother Arnie in 1994. Even though it was Johnny Depp that played the lead role, Leo stole the show with his incredible performance as the disabled younger brother earning his first ever Oscar nomination of his career.

The Aviator
Moving from supporting actor to lead, in 2005 DiCaprio was once again nominated for his role as billionaire and aviation tycoon Howard Hughes. Besides doing a fantastic job portraying the eccentricities of this American legend, it was his ability to accurately exemplify his aging process that made him worthy of an Oscar.

Blood Diamond
In 2007 another Academy Awards nomination came his way for his character, Danny Archer, in Blood Diamond. I think the most memorable part of this character was not just Leo’s ability to demonstrate his dramatic skills but also his mastery of the very difficult South African accent.

Django Unchained
The only non-Oscar nominated one in our list is by far my favourite. Leo played Calvin Candie and almost earned himself a Golden Globe for his supporting role in Django Unchained. During one of the scenes, DiCaprio accidentally cut his hand on broken glass but where weaker actors would yell cut, DiCaprio continued the scene, never breaking character. His bloodied hand made it into the final cut of the movie and apparently everyone erupted into a standing ovation after the take was over.

The Wolf of Wall Street
Who can forget Leo’s enigmatic portrayal of Jordan Belfort, founder of Stratton Oakmont. Yes, the actor gave an impressive Awards-worthy performance but in 2014, the Academy Awards race for best actor was just too much for poor Leo and he lost out to Matthew McConaughey as Ron Woodroofdouble-dagger in Dallas Buyers Club. He did win a Golden Globe for it though.