Can Clint Eastwood Become the Oldest Oscar Winner Ever for Cry Macho? 

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Last week, Hollywood legend Clint Eastwood announced his return to the big screen. The 91-year-old actor/director is set to star in the upcoming film Cry Macho which will be released in theaters and on HBO Max on September 15. The trailer for the movie, which is based on a 1975 book of the same name, was unveiled on Friday.

In an interview with Entertainment Weekly, Eastwood said,

“It’s about a man who has been through some hard times in his life and then unexpectedly another challenge is brought to the foreground. He would normally never do it but he is a man of his word. He follows through. And it starts his life over again.”

Eastwood plays Mike Milo, a former rodeo cowboy who agreed to help his former boss get his son out of trouble in Mexico. As is usually the case with Eastwood’s work these days, he not only stars in Cry Macho, but he is also the director and one of the lead producers.

Eastwood’s Decorated History at the Oscars

If Eastwood himself or Cry Macho earns any nomination at the 94th Oscars, Eastwood would become the oldest person to ever earn an Oscar nomination in any category. Eastwood turned 91 in May, but he is showing absolutely no signs of slowing down.

The do-everything Hollywood star has earned a total of 11 Oscar nominations for his work over the years, with four wins to his name. He won Best Director for 1992’s Unforgiven and 2004’s Million Dollar Baby, with both movies also taking home Best Picture honors in those same years.

However, Eastwood has never won Best Actor despite having been among the nominees for the award twice. He was nominated for Best Director for both Mystic River and Letters from Iwo Jima, as well, while American Sniper was beaten for Best Picture honors in 2014 by Birdman.

Just last year, the 83-year-old Anthony Hopkins became the oldest person to win Best Actor when he took home the prize for his work in The Father. If Cry Macho ultimately lives up to the hype, however, Eastwood could make sure Hopkins’ record is short-lived.

Eastwood can also break his own record if he takes home Best Director. Eastwood is already the oldest Best Director winner after he won for Million Dollar Baby as a 74-year-old. If he simply earns a nomination, though, he would break John Huston’s record for the oldest Best Director nominee. Huston was 80 when he was nominated for the award in 1986 for Prizzi’s Honor.

Could Eastwood’s Politics Hurt His Chances?

Unfortunately, U.S politics these days seem to go hand-in-hand with American pop culture. While many Academy Award winners choose to use their acceptance speeches as platforms to promote their own political ideologies, it seems as though the vast majority of them fall under a similar political umbrella.

Unlike most left-leaning Hollywood stars, though, Eastwood has been a vocal supporter of Republican politics for most of his public life. He said he would be voting for Republican John McCain in 2008 before he publicly endorsed Mitt Romney ahead of the 2012 presidential election. That same year, he infamously delivered a keynote speech during the Republican National Convention. Eastwood made headlines for delivering a bizarre, rambling speech to an empty chair on stage that was, apparently, supposed to represent then-president Barack Obama.

However, things may have shifted in recent years. Eastwood did not officially endorse any candidate ahead of the 2016 election before throwing his support behind Democratic candidate Mike Bloomberg during Bloomberg’s brief run last year. Bloomberg was running as a moderate Democrat, but he previously served three terms as the mayor of New York City as a Republican. Way back in 1952, Eastwood officially registered as a Republican in order to support Dwight Eisenhower’s campaign before backing Richard Nixon in both 1968 and 1972.

While Eastwood’s personal political views may differ from many of his Hollywood colleagues, it’s also fair to say that being a Republican hasn’t hurt him when it comes to winning awards over the years. The political landscape has shifted considerably since Eastwood’s strange speech at the 2012 RNC, but that is unlikely to cost him a chance at winning another Oscar early next year. If Cry Macho is worthy, the awards nominations will follow.

Eastwood and Cry Macho Both Oscars Long Shots

It’s only August, so a lot can change between now and the 2022 Academy Awards next March. That said, both Eastwood and Cry Macho are facing long odds to earn recognition at the Oscars next year.

As of now, Cry Macho is listed at +10000 to win Best Picture at the Oscars next year at entertainment betting sites. Nightmare Alley has opened as a +850 favorite, followed by Soggy Bottom (+950), The Tragedy of Macbeth (+950), House of Gucci (+1000), Dune (+1200), and West Side Story (+1200).

Eastwood himself has been priced at +10000 to win the Best Actor Oscar for the first time in his career, as well. Denzel Washington has emerged as a +850 favorite for his starring role in The Tragedy of Macbeth, while Adam Driver, Will Smith, Bradley Cooper, and Benedict Cumberbatch have favorable odds of their own. Leonardo DiCaprio, Joaquin Phoenix, and Michael B. Jordan are among the other stars with new films set to debut before the end of 2021.

Eastwood has found most of his Oscars success in the Best Director category, but he’s once again facing long +10000 odds to win it for the third time in 2022. Paul Thomas Anderson checks in as the early +500 favorite for Soggy Bottom, with Jane Campion (+600), Guillermo Del Toro (+600), and Joel Coen (+650) listed among the early hopefuls at entertainment betting sites.

It’s safe to say that Eastwood and Cry Macho will both have plenty of competition when it comes to winning major awards next year. However, if you do want to take a flier on the long odds, I don’t mind a stab at Eastwood’s +10000 odds to win Best Director. This is typically one of the more wide-open categories when it comes to betting on the Oscars, and Eastwood’s favorable track record makes him a legitimate contender.

If you want to bet on Eastwood’s 2022 Oscars odds, take a chance on the 91-year-old to take home Best Director.

Taylor Smith

Taylor Smith has been a staff writer with since early 2017. Taylor is primarily a sports writer, though he will occasionally dabble in other things like politics and entertainment betting. His primary specialties are writing about the NBA, Major League Baseball, NFL and domestic and international soccer. Fringe sports like golf and horse racing aren’t exactly his cup of tea, bu ...

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