Leonardo DiCaprio and the 'Deserved' Oscar

DiCaprio at the 2016 Golden Globes. (Getty)

Inevitable is the first word that comes to mind when you describe Leonardo DiCaprio’s Oscar chances; deserved, a close second.

The inevitable part is easy to explain: In the run-up to Sunday’s 88th Academy Awards, DiCaprio has owned the Best Actor competition. He has won the Screen Actors Guild Award, the BAFTA, and the Golden Globe. Some risk-averse oddsmakers have set his Oscar line at 1 in 100, meaning he’s considered such a heavy favorite to claim the statuette for The Revenant that you’d have to bet $100 to earn a single buck on a DiCaprio win.

Nearly every major betting service has DiCaprio at overwhelming odds to win. (EasyOdds.com)

The deserved part is likewise easy to explain: Oscar voting ain’t science. It’s subjective.

“It’s an industry town. It’s so inside,” says Jim Piazza, co-author, with Gail Kinn, of The Academy Awards: The Complete History of Oscar.

Votes can be driven by factors so intensely personal that if “you give people cheap wine [at a screening or event], they’re going to retaliate,” Piazza says.

On the flip side, voters can be swept up in the romantic notion that it’s an actor’s time — that an actor “deserves” a win.

Kate Winslet is a member of the Oscar club whose own victory for 2008’s The Reader, after five previous nominations — and losses — was considered of the “it’s time, she deserves it” variety. She has been openly campaigning for her former, and forever, Titanic co-star. “I think you can sort of feel it. And I think that everyone wants it for him, and it would be amazing,” Winslet told Reuters. “I think you can sort of feel the temperature, it’s probably going to be Leo’s year.”

Winslet and DiCaprio share a moment after his SAG Award win. (TBS)

Winslet is a nominee herself this year for Best Supporting Actress for Steve Jobs, and, after BAFTA and Globe wins, she’s a nominee with a solid shot. This time out, however, she’s not a nominee with a DiCaprio-esque backstory.

Though a relatively spry 41, DiCaprio has been losing at the Oscars for more than 20 years. He was first nominated at age 19 for What’s Eating Gilbert Grape? He was famously not nominated for Titanic (and Gangs of New York, Catch Me if You Can, and The Departed). He was denied for his crowd- and critic-pleasing work in The Wolf of Wall Street, losing to Dallas Buyers Club’s Matthew McConaughey, an actor with his own compelling comeback storyline.

DiCaprio at the 1994 Oscars for Gilbert Grape. (WireImage)

In all, DiCaprio has nothing to show — yet — for five career Oscar nominations. In awards-show parlance, as in baseball parlance, he’s due. He’s Julia Roberts, claiming her triumphant Erin Brockovich trophy (at an even sprier 33). He’s Denzel Washington, “finally” taking that Best Actor statuette (after an earlier Best Supporting Actor win) for Training Day. He’s Julianne Moore, breaking her own 0-for-4 Oscar losing streak with a victory for Still Alice.

“I think there is a definite cumulative effect,” says Glenn Whipp, who covers awards season for the Los Angeles Times. “Like when [DiCaprio] won the Golden Globe, the ovation he received in that room was second only to [Sylvester] Stallone’s in terms of heartfelt ‘It’s great to see [him] winning.’”

(For those keeping track of Oscar narratives at home, the 69-year-old Stallone, who’s up for his first Academy Award in 39 years for the Rocky spinoff Creed, is what’s known as the “sentimental favorite.”)

If DiCaprio had only the “he’s never won before” factor going for him, however, he might not be thought to be so far ahead of his competition. The “he’s due” argument obviously never worked for either Richard Burton or Peter O'Toole, both of whom died without ever cashing in on a single one of their combined 15 nominations. (O'Toole did receive an honorary Oscar.)

No one-trick pony this time out, DiCaprio also has the “he deserves it because he suffered for his art” thing. Or, as a Vanity Fair headline flatly put it, “Leonardo DiCaprio Slept in Animal Carcasses and Ate Bison Body Parts for The Revenant.”

The Revenant (20th Century Fox)

“This isn’t a vote for career achievement. He did a great job,” one unnamed Academy member told Entertainment Weekly. “I felt for his character and for what he was going through.”

(The same Oscar voter, by the bye, copped to casting a ballot for Stallone “based on nostalgia.”)

About the only sector that the DiCaprio Oscar campaign isn’t hitting is “he deserves it because he’s overdue.” Due is one thing; overdue is another. Screen legend Henry Fonda, ailing and Oscar-less at age 76 when he was up for On Golden Pond, was overdue; Paul Newman, 0 for 7 in competitive Oscars and age 62 when he was up for The Color of Money, was overdue.

“'Overdue Oscars’ are absolutely a real thing,” says Scott Feinberg, awards-season analyst for the Hollywood Reporter. “I don’t think Leo is an example of this, though, because his performance in The Revenant is certainly among his best.”

Feinberg’s comment speaks to the idea that “due,” “overdue,” and “deserved” Oscars, in fact, don’t always represent an actor’s best work.

Piazza, for one, says it’s rare for Oscar voters to get it right — to find the year’s best performance and, absent of sentiment, to honor that performance. For every Meryl Streep winning for Sophie’s Choice (one of Piazza’s picks to click), there’s Al Pacino losing for career-defining roles in The Godfather, Serpico, and Dog Day Afternoon and winning for Scent of a Woman.

“The only time Hollywood gets it right, it’s an accident,” Piazza says, paraphrasing an old saying of the studio-system era. “[But then] how many times does the right person win for president?”

Now, there’s a disquieting thought. Better to tune in for a couple of hours on Sunday, and enjoy DiCaprio’s “deserved” Oscar.