Long before Donald Trump became one of the most polarizing figures in American politics, he was a familiar face among celebrities, socialites, athletes, and entertainment power players.
Throughout the 1980s and 1990s, Trump regularly attended high-profile galas, charity events, sporting contests, and Manhattan nightlife gatherings.
He posed for photos with some of the biggest stars of the era and moved comfortably through elite celebrity circles.
That history makes criticism from certain entertainers especially fascinating. Many of them are not commenting on Trump from a distance. They knew him, socialized with him, and watched his public rise firsthand.
One of Trump’s most persistent celebrity critics has been actress, singer, and comedian Bette Midler.
For years Midler has used social media, interviews, and television appearances to blast Trump’s MAGA and often bigoted rhetoric, policies, and leadership. Sometimes she doesn’t have to say anything.
Her latest diss came after Trump attended Game 3 of the NBA Finals between the New York Knicks and San Antonio Spurs at Madison Square Garden on Monday.
Trump made history as the first sitting U.S. president to attend an NBA Finals game. But his appearance also generated controversy.
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According to reports, some ticketholders waited for hours in security lines that stretched more than two blocks because of the enhanced security surrounding the president’s visit. While Trump received applause from some fans, videos circulating online also captured audible boos inside the arena.
Trump booed very loudly here at MSG pic.twitter.com/IeQwwqGtop
— Esfandiar Baraheni (@JustEsBaraheni) June 9, 2026
The Knicks ultimately lost 115-111, narrowing their series lead to 2-1.
Midler couldn’t resist weighing in.
View on Threads
The 80-year-old reposted a meme that read, “Booing the president of our country during the national anthem is not appropriate. We should be booing him during other songs too.”
She added, “And like, during press conferences. And when he’s sleeping. Or golfing. Just like all the time, really.”
Many people weighed in on Threads.
“I was so friggin proud on NYC,” one quipped. Another wrote, “Apparently he cannot decipher between boos and shouts of encouragement- we need to be voicing in unison ‘8647’ – maybe he would understand that.”
“You almost had me there, but I like where this went,” one wrote.
“Hahahaha! First, I was getting mad, and then I could not stop laughing! Even my dog started laughing!” joked another supporter.
“I’ve been a fan of yours since the 70’s. So good to know you have not altered your irreverence!” one wrote. Someone else said, “Did you ever know that you’re my hero? (okay I’ll see myself out).”
The NBA Finals joke was only the latest chapter in Midler’s years-long public feud with Trump.
Following Trump’s victory over former Vice President Kamala Harris, Midler was so upset that she spazzed out online and then deactivated her X account.
Before leaving the platform, she shared a lengthy quote from early 20th-century columnist H.L. Mencken criticizing voters and politicians.
“When a candidate for public office faces the voters he does not face men of sense; he faces a mob of men whose chief distinguishing mark is the fact that they are quite incapable of weighing ideas, or even of comprehending any save the most elemental — men whose whole thinking is done in terms of emotion, and whose dominant emotion is dread of what they cannot understand,” she quoted.
The post generated backlash from Trump supporters, many of whom objected to the suggestion that voters were incapable of weighing ideas for themselves.
In 2025, Midler took her criticism directly to late-night television.
Appearing on “The Late Show With Stephen Colbert,” she used a parody version of her classic song “Wind Beneath My Wings” to praise the comedian while taking shots at Trump.
The appearance came after CBS announced Colbert’s show would end in 2026 despite strong ratings. The cancellation sparked speculation online because it followed Trump’s settlement of a multimillion-dollar lawsuit involving the network.
During the appearance, Midler emotionally told Colbert, “I want to beg you, don’t go.”
She continued, “I would not have made it through without you. I really wouldn’t have. You’re a voice of sanity and reason and honesty and most important, honor.”
She later performed a humorous parody that included the lyric, “you never kissed the orange a**.”
Trump eventually responded on Truth Social, writing, “I absolutely love that Colbert got fired. His talent was even less than his ratings.”
Whether she’s posting memes, parodying songs, or sharing political commentary, Midler has remained one of Trump’s most vocal celebrity adversaries.
Their public clashes also highlight a larger cultural shift. Decades ago, Trump and many entertainers occupied the same celebrity ecosystem. Some of those same figures have become his loudest critics today.
The old photographs may show smiles and handshakes. The modern headlines tell a very different story.
