Leonardo DiCaprio is heading into his fifth collaboration with Martin Scorsese with The Wolf of Wall Street this November. He is Scorsese’s Jimmy Stewart — a laced-up-to-the-collar everyman put in extraordinary circumstances. He anchors Scorsese’s camera by adding a down to earth normalcy. With De Niro, you think you know what you’re going to get — a darkness that worked for Scorsese’s Taxi Driver and Raging Bull. But the director needed a new hero, one who could change his color with each new atmosphere he was put into. De Niro was uncorked, back in the 1970s, the minute he appeared on screen. You waited for his flame to rise. With DiCaprio, you never know where he’s going to take you. You never know what his breaking point is, what might set it off, or how far or deep he will go. The trailer for Wolf is a dazzler and promises another inspired, trusted collaboration between artist and muse. Scorsese’s actors keep so much in that when they finally uncork it’s a spectacular display of emotional and physical extremes. In their first collaboration together, DiCaprio played the protagonist while giving the movie mostly over to the brilliant Daniel Day-Lewis as Bill the Butcher. Gangs would be their first mob movie together, which would be followed up by The Departed, and now, Wolf of Wall Street. Though DiCaprio would be paired up with another scene-stealer in Jack Nicholson, he was the one really coming unglued in The Departed. In The Aviator Scorsese facilitated one of DiCaprio’s most difficult performances and one of his best — it’s certainly way up there. As the nervous, stuttering, withering Howard Hughes, DiCaprio surprised everyone with his ability to play Hughes at every stage of his life. It would be his first leading actor Oscar nomination, with his second and last for Blood Diamond in 2007. He wasn’t nominated for Gangs, or The Departed, or Shutter Island, or Revolutionary Road, or Inception, or J. Edgar, or Django Unchained. It makes you wonder, what do the Academy of Motion Pictures Arts and Sciences have against Leonardo DiCaprio? Some would say, like Tom O’Neil at Gold Derby, that the Academy hold grudges, or don’t take seriously, golden boys, or pretty boys. After all, one of them is headed for only his second Oscar nominations in four decades — Robert Redford who will be up for a win with All is Lost. Paul Newman didn’t win Best Actor until The Color of Money, after six acting nominations. Some might say, well Colin Firth is a pretty boy, why did he win so easily? But Colin Firth is British so that lends some “respectability” to the Anglophiles in the Academy. But he also had a significant disability, catnip for Oscar voters. Give them a major disability, make them gain weight, ugly them up? Had DiCaprio gained thirty pounds to play J. Edgar they would have taken notice. But as such, they figure the guy has everything already — good looks on top of power, wealth and fame. Why would they need an Oscar? No nominations for DiCaprio’s deserving work could also go back to his early career. First he was nominated for Gilbert Grape and considered, at the time, one of the most promising young character actors. But then he did Titanic. Once he became the most desired man in the world his paychecks skyrocketed. Suddenly, the promising character actor, destined to play hunchbacks and drug addicts, was dating the most beautiful models in the world, jet-setting around with the beautiful people. It wouldn’t do. Despite the celebrity he became, the quality of DiCaprio’s work has not diminished. There probably isn’t a harder-working lead actor than DiCaprio. Studio execs like to sign him because they know he brings in the box office numbers; Directors like working with him because he’s a damned fine actor. He has so many fans that decent box office is part of the deal. But he never had to work as hard as he has to prove himself as an actor. He’s always willing to try new things, to go the darkest places and to find his own tipping point. That tipping point has been best accessed by his collaborations with Scorsese. As someone who writes about the Oscars, I am often asked by people why DiCaprio has been so often ignored, and why he’s never won an Oscar — but also, why he never gets acknowledged for his brilliant work time and time again. I don’t have any easy answer that would satisfy. Some say he has a baby face and he can’t scrub that off, not even with heavy makeup. Some say he’s no adept with accents and should never try to do them — though he handled his Boston accent as fluently as anyone besides the Boston-born Mark Wahlberg and Matt Damon. Maybe the worst case of awards negligence in DiCaprio’s impressive career was last year’s Django Unchained debacle. Although Christoph Waltz was co-lead in Django, the Academy choose to nominate him in the supporting category over DiCaprio — and then award Waltz with another Oscar for basically playing the same part as he played in Inglorious Basters was, to me, a true low point in lazy Academy voting. In fact, it’s so depressing to even think about it’s best not to go there. Waltz is great. His part is great. But he’s a co-lead character alongside Foxx. Waltz’s screen time and number of lines gave him an unfair advantage and represents Academy voting at its most lazy and Emmy-like. So if you ask me why the Academy repeatedly ignores DiCaprio, the honest answer is — I have no clue. I don’t understand the male mind and never have. Since we now know the Academy is 70% white, straight, middle-aged male, you will have to ask one of them to explain why. To me, DiCaprio is only getting better, more daring, more exciting to watch. I even thought he turned in some of his work to date in The Great Gatsby. From the looks of The Wolf of Wall Street trailer we are in for another great one from both DiCaprio and Scorsese. What does that mean for Oscar? It means there’s a good chance that another of their collaborations will result in multiple Oscar nominations — Shutter Island (greatly underrated), notwithstanding — although DiCaprio himself has only benefited once. One of the things we’ll remember about this era when we look back in decades to come is how little regard the industry seemed to have for DiCaprio whenever awards season rolled around, despite his consistent determination to challenge his own boundaries as an actor, and his ability to keep his core audience, his fans, coming back for more.