Best Actor: The Battle of the Overdue

Call them "The Overdue."

There is nothing on Oscar night that causes the crowd at the Dolby Theatre to leap to their expensively shod feet quicker than when one of their own is finally rewarded with a trophy after years of waiting, especially if they are a well-liked A-list talent and a major box-office draw.

Recall the rousing reception when Sandra Bullock at long last made it to the podium after winning for her feisty Southern lady who stands up for her adopted football star son in 2009’s “The Blind Side”—her first-ever nomination.  The rom-com queen had to show her more serious side to get there, but sometimes changing up your image can do wonders to make the film industry appreciate you anew.

That same year, Jeff Bridges—whose first of six nominations was for 1971’s “The Last Picture Show”—finally took the prize on his fifth try as a boozy old country singer trying to make a fresh start in “Crazy Heart.” It might not have been his career-peak performance, but it was worthy enough to allow his statuette to serve as a sort of lifetime achievement honor for his incredible body of work. The Dude abides.

This year, the race is already shaping up to have several actors who might qualify for “it’s about time” status. Mark Ruffalo, nominated twice before, could face off in the supporting category for his determined reporter in “Spotlight” against co-star Michael Keaton, who might get his second shot at an Oscar as Ruffalo’s dedicated editor. Perhaps this would take the sting out for having his anticipated lead win for last year’s “Birdman” plucked away by Eddie Redmayne in “The Theory of Everything.” 

Given the universal love for “The Martian,” Matt Damon might score his third chance at an acting Oscar (he shared a win for Best Original Screenplay with Ben Affleck for 1997’s “Good Will Hunting”) as a lost-in-space astronaut. And don’t discount two-time nominee Will Smith as a real-life Nigerian doctor who investigates the damaging effects of sports head injuries in “Concussion.”

And who knows? Perhaps Samuel L. Jackson in “The Hateful Eight” will get another gift from Quentin Tarantino that rivals his hitman Jules in 1994’s “Pulp Fiction,” the source of his lone Oscar nod.

There are fewer actresses this year that qualify as being too long denied, although “Grandma’s” Lily Tomlin has been waiting four decades since her film debut in “Nashville” to have another legit chance at the gold. Meanwhile, it’s a crime that Jennifer Jason Leigh, who has a supporting role in “The Hateful Eight,” has never been nominated at all.

But the most intriguing clash of the Oscar-less titans will likely be between two of filmdom’s most popular male stars who each have come away empty-handed several times in the past on Hollywood’s big night: Johnny Depp and Leonardo DiCaprio. 

Depp’s much-praised portrayal of brutal Boston crime boss Whitey Bulger in “Black Mass” and DiCaprio’s ferocious depiction of a vengeance-seeking fur trapper in “The Revenant”—which likely won’t screen until closer to its Dec. 25 opening—have both one-time teen idols embracing their dark side and eschewing all vanity. And Academy voters love it when handsome stars sacrifice their looks for a role, as demonstrated by such past winners as George Clooney in “Syriana,” Matthew McConaughey in “Dallas Buyers Club” and Christian Bale in “The Fighter.”

Despite their disparate resumes—puckish joker Depp has a taste for goth and quirkiness, while drama king DiCaprio relishes heavy emoting—the cast mates from 1993’s “What’s Eating Gilbert Grape” have followed somewhat similar paths to fame and fortune. Their first major big-screen parts were in horror films, Depp in 1984’s “A Nightmare on Elm Street” and DiCaprio in “Critters 3.” They each paid their TV dues early on, with Depp as an undercover cop on “21 Jump Street” and DiCaprio appearing on the sitcom “Growing Pains” and the soap opera “Santa Barbara.”

And they both have engaged in an ongoing collaboration with two of America’s most distinctive filmmakers. With their shared admiration of the macabre and twisted humor, Depp and Tim Burton’s soon-to-be nine features  together represent one the most successful actor-director pairings ever, starting with 1990’s “Edward Scissorhands” and continuing with next year’s “Alice in Wonderland” sequel. Meanwhile, Martin Scorsese helped to rescue DiCaprio from his post-“Titanic” heartthrob limbo beginning with 2002’s “Gangs of New York,” and they have a sixth project in the works, “Devil in the White City,” about America’s first serial killer.

Their parallel paths just make their potential showdown this awards season that much more intriguing. Obviously, they both could lose. The most likely candidate to cause an upset at the moment is Michael Fassbender, a previous supporting nominee for “12 Years a Slave,” who has a legion of admirers and is getting some of his best reviews ever as the enigmatic title character in “Steve Jobs.” And what to make of Depp’s recent revelation to BBC Newsbeat, in which he said in an interview, “I don’t want to win one of those things ever, you know. I don’t want to have to talk. They gave me one of those things, like a nomination, two or three times. A nomination is plenty.”

That is either an act of coyness, a ploy to get out of doing endless campaigning or the most perversely genius way to convince the voters to actually give you the award.

But, nonetheless, it is still an interesting exercise to see how Depp and DiCaprio stack up side by side—and who might have the edge come Oscar time.

Pros and Cons For a Depp Win 

The breadth of previous nominated roles: Depp has only three lead nominations to DiCaprio’s three leads and a supporting nod, but you can’t ask for more variety than a buccaneer (Capt. Jack Sparrow in “Pirates of the Caribbean: The Curse of the Black Pearl,” 2003), a famous writer (“Peter Pan” creator J.M. Barrie in “Finding Neverland,” 2004) and a Stephen Sondheim musical madman (“Sweeney Todd: The Demon Barber of Fleet Street," 2007).

The Oscar-bait-worthiness of his “Black Mass” performance: In addition to donning ice-blue contacts and thinning his hair to transform into a murderous monster, Depp will benefit from pulling off a deadly serious role that is worlds apart from his lightweight characters in such recent disappointments as “Mortdecai,” “The Lone Ranger” and  “Dark Shadows." Also, four out the five lead actor winners since 2010 have played real-life characters.

Is the movie a Best Picture contender? You can get nominated without your film making the cut. But it is harder to win an Oscar if the movie isn’t competing in the top category. The past five winners all starred in best-picture candidates. “Black Mass” ended up with a 75% positive score on Rotten Tomatoes, but most critics raved more over Depp than the movie itself. Also not helping: A stalled worldwide box-office take of just $56 million. Then again, director Scott Cooper was behind the last film to not be nominated yet win for Best Actor, “Crazy Heart.”

His age: At 52, the perpetually youthful Depp is starting to show his age—and that might work to his advantage.

The wait: It has been 12 years since his first nomination.

Oscar oversight: Atypically introspective and fully invested, Depp gave one of his best dramatic performances in 1997’s “Donnie Brasco” as a real-life FBI agent who goes undercover to infiltrate the Mob and grows close to Al Pacino’s aging hitman. He deserved a nomination just for his soliloquy explaining the term “fuggedaboutit.”

Mitigating factor: Only one lead actor has ever won an Academy Award by playing a mobster—Marlon Brando as Don Corleone in 1971’s “The Godfather.“ A few others have gotten nominations—Al Pacino in 1974’s “The Godfather II,” James Cagney in 1938’s “Angels With Dirty Faces”—but organized crime doesn’t usually pay off in Oscar gold. 

How many actors failed to win by their fourth attempt? Besides DiCaprio, Warren Beatty, Ed Harris, Charles Boyer and Claude Rains came away empty handed after four times at bat. Just OK odds for Depp, especially considering the caliber of the talent that was overlooked. 

Did he ever produce a Best Picture nominee? Yes. Although not officially a nominee himself, Depp was one of the producers on Scorsese’s “Hugo” from 2011. 

Pros and Cons For a DiCaprio Win

The breadth of previous nominated roles: DiCaprio has shown a phenomenal range, starting at age 19 with his supporting nod for playing Depp’s mentally-challenged brother in 1993’s “What’s Eating Gilbert Grape.” His first lead nomination was for his portrait of studio mogul and aeronautic pioneer Howard Hughes in 2004’s “The Aviator” followed by his cocky African mercenary turned smuggler in 2006’s “Blood Diamond.” Meanwhile, in 2013, the actor got a rare chance to display his comic chops in the pitch-black “The Wolf of Wall Street” as swindling stockbroker and buck-wild party boy Jordan Belfort.