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Trump and Hollywood’s 10 Rockiest Relationship Moments of 2019

Back in the old, naive, innocent days of say, five years ago, few imagined that a wealthy reality TV star would turn his on-screen schtick into a four-year term (well, maybe) as president of the United States. But Hollywood’s loss has been America’s … never mind.

Once Trump ascended to that towering perch, he began to tweet the hand that fed him not just daily, but sometimes 150 times a day! In year three of his presidency, with impeachment now in the history books and few showbiz allies, the spats, insults and threats continued unabated. And the stakes were raised even higher when support did show up in the form of celebrities with higher profiles than Scott Baio and John Ratzenberger.

JANUARY: It didn’t take long for Hollywood to start the New Year with a fresh skewering of Trump, especially when it was in the service of taking down a film competing for the best picture Oscar. Someone found “Green Book” screenwriter Nick Vallelonga’s pro-Trump/anti-Muslim social media post from four years earlier and voila, the Oscar flambe began. The writer’s quick mea culpa maxima must have worked because the film won the best picture Academy Award and Vallelonga also went home with Oscar screenwriting gold.

And the New Year pounding of Trump continued in January, courtesy of Jimmy Kimmel’s tongue-in-cheek “Halftime Tribute to Trump.”

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FEBRUARY: What could be a more perfect occasion for a presidential meltdown than the long-overdue honoring of groundbreaking filmmaker Spike Lee at the Oscars?

MAY: This was the year that Kanye West threw his support behind Jesus Christ as the spiritual savior of the world and for Donald Trump as the political salvation of our troubled nation. The former endorsement seems to be going pretty well, with sold-out shows and lots of merch moving off the shelves. But has his support for the president convinced his followers? Not so much.

JULY: It takes a reality star to successfully lobby a reality star. Just as Trump successfully (you could argue pro and con) reinvented himself from Mr. Apprentice to Mr. President, Mrs. West, a.k.a. Kim Kardashian, has gone from Mrs. Social Media Queen to Mrs. Criminal Justice Reformer. The good news: Criminal justice reform, an extremely worthy cause, is now trending.

AUGUST: Like “Cats,” Universal and Blumhouse’s thriller “The Hunt” must have looked good on paper, but oh dear, at least the felines made it into theaters. Based on the premise that liberals might enjoy hunting and killing “deplorables,” the film’s impending release sent Trump into a frenzy and the film’s studio into reverse.

SEPTEMBER: Fools rush in where angels fear to tweet, but that didn’t stop TV star Debra Messing from mixing it up online with the tweeter-in-chief. What caused Messing to throw caution to the winds? Mass shootings, hurricanes and a $15 million grossing Beverly Hills Trump campaign fundraiser, she said.

NOVEMBER: Two baby boomers, both born in the ‘40s in New York City, one in the borough of Queens, the other in Manhattan. One the son of a noted painter, the other the scion of a self-made real estate mogul. But boy, do they not get along. One week Robert De Niro is calling Trump a motherf—er, the next he’s wishing for a bag of excrement to whack him in the face. Can their feud get any hotter? Don’t bet against it.

The list of Hollywood A-listers who support Trump is seemingly getting shorter by the day so it must have been irresistible to pin a medal on Jon Voight, a guy who was once one of Hollywood’s brightest stars.

DECEMBER: For some in Hollywood, Christmas came early with the news that the Nancy Pelosi-led Democrats in Congress had written a script almost everyone west of La Brea was sure to love: it’s called “Impeachment.”

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