Donald Trump's Most Cringe-Worthy TV Appearances

Donald Trump has worn many hats throughout his life. Initially, he was best known as a New York real estate developer with a bombastic personality and a penchant for slapping his name on his buildings. Then, in the late 1980s, Trump branded himself as an author, whose entirely ghost-written book, "The Art of the Deal," became a bestseller. He eventually branched out into hawking an array of Trump-branded products (ranging from bottled water and mail-order steaks to vodka and Success cologne), and in the 2000s, achieved reality television stardom with "The Apprentice" and its successor, "The Celebrity Apprentice." It all culminated with a four-year stint in the Oval Office, during which he was impeached — twice! — before running unsuccessfully for a second term. He once again declared himself a candidate for the presidency, but this time his campaign was hampered by a jaw-dropping number of criminal and civil indictments, which have pretty much led him to become a part-time presidential candidate and full-time defendant.

In the midst of it all, Trump has continually demonstrated an outsized love of TV cameras; numerous reports, in fact, have indicated that when Trump isn't appearing on television, he's watching it. 

Some of those on-camera moments have become highly memorable, albeit for all the wrong reasons. For a closer look, read on for a look at Donald Trump's most cringe-worthy TV appearances.

Donald Trump's starring role on NBC's "The Apprentice" led to a bizarre moment nobody could have seen coming when he participated in an onstage bit at the 2005 Emmy Awards. Joined by fellow NBC star Megan Mullally (in character as Karen Walker from "Will & Grace"), Trump took to the stage wearing a frayed straw hat, white t-shirt, and denim overalls while brandishing a pitchfork as the two sang a duet: The theme song from 1960s sitcom "Green Acres." 

Once ensconced in the White House, Trump unexpectedly resurrected the bit in 2018 when he tweeted the video in conjunction with the Farm Bill he was about to sign. Mullally, evidently looking back at the moment with regret, tweeted, "If you guys need me, i'll be in a hole in the ground." 

While Trump may have performed at the Emmys, he's never won one. A decade later, it was clear this fact was still sticking in his craw during one of his 2015 debates with rival presidential candidate Hillary Clinton. "There was even a time when he didn't get an Emmy for his TV program three years in a row, and he started tweeting that the Emmys were rigged against him," Clinton said, more than a little presciently. "This is a mindset. This is how Donald thinks. And it's funny, but it's also really troubling." Trump's response only proved her point. "Should have gotten it," he complained. 

While promoting "The Apprentice," Donald Trump was joined by daughter Ivanka for a 2006 appearance on "The View." When asked how he'd react if Ivanka would pose for Playboy — a pure hypothetical, by the way — he offered a response that guaranteed to take him out of the running for any Father of the Year competitions. 

"It would be really disappointing — not really — but it would depend on what's inside the magazine," Trump said (via "Today"), and then added, "I don't think Ivanka would do that, although she does have a very nice figure. I've said if Ivanka weren't my daughter, perhaps I'd be dating her." Joy Behar then quipped, "Who are you, Woody Allen?"

If that's how Trump speaks about his daughter on national television, what does he say about her in private? That was revealed in the book "Blowback: A Warning to Save Democracy from the Next Trump," written by Miles Taylor, former chief of staff to Homeland Security Secretary Kirstjen Nielsen during Trump's presidency. "Aides said he talked about Ivanka's breasts, her backside, and what it might be like to have sex with her, remarks that once led [former White House chief of staff] John Kelly to remind the president that Ivanka was his daughter," Taylor alleged in an excerpt published by Newsweek. "Afterward, Kelly retold that story to me in visible disgust. Trump, he said, was 'a very, very evil man.'"

Among Donald Trump's most memorable scandals was his infamous conversation with "Extra" host Billy Bush, who yukked it up while Trump bragged about the ease with which he could non-consensually fondle women (and worse) due to his stardom. The fallout from those shocking remarks was, to be frank, unexpected, in that Trump was subsequently elected president, and Bush was fired from "Today" for laughing along at what Trump later dismissed as "locker room talk."

Those comments, however, were right on brand with a similarly cringe-worthy statement he made during a 2013 episode of NBC's "The Celebrity Apprentice." During a boardroom session, rocker Brett Michaels told Trump that former "Baywatch" star Brande Roderick dropped to her knees and begged not to be fired. "Excuse me, you dropped to your knees?" Trump interjected, addressing Roderick, who confirmed that she had. "Must be a pretty picture, you dropped to your knees," Trump said lasciviously, prompting Roderick to smile weakly and then avert her eyes from Trump's gaze.

According to an AP report, interviewing numerous staffers from the show, that was mild compared to some of the stuff Trump said that didn't make it on the air. Randal Pinkett, who won the 2005 season of "The Apprentice," told AP that Trump openly discussed which of the female contestants he'd enjoy sleeping with. Meanwhile, former "Apprentice" contestant Summer Zervos has claimed that Trump groped and kissed her on two separate occasions.

When Donald Trump announced he was officially running for president, he made a statement that many people found to be not only over the line but overtly racist. Discussing his plans to halt illegal immigration at America's southern border, Trump made a sweeping generalization about an entire country. "When Mexico sends its people, they're not sending the best," he stated. "They're sending people that have lots of problems, and they're bringing those problems. They're bringing drugs, they're bringing crime. They're rapists, and some, I assume, are good people, but I speak to border guards, and they're telling us what we're getting."

Trump's remarks whipped up instant controversy, and the fallout was rapid. NBC, the network that aired "The Celebrity Apprentice," announced it was turning the tables by firing Trump (he was later replaced by Arnold Schwarzenegger). In addition, NBC also axed deals to broadcast Trump's Miss USA and Miss Universe pageants, as did Spanish-language network Univision. "Due to the recent derogatory statements by Donald Trump regarding immigrants, NBCUniversal is ending its business relationship with Mr. Trump," a statement from the network read. "At NBC, respect and dignity for all people are cornerstones of our values."

Trump responded in an extensive statement on Facebook, asserting that "illegal immigrants are committing substantial amounts of crime," and he criticized NBC for being "weak and foolish" in their decision to cut all ties with him.

To Donald Trump's credit, NBC did indeed look "weak and foolish" when he was invited to host "Saturday Night Live" just a few months after the network had fired him. The decision to tap Trump as host proved controversial; Rockefeller Center in Midtown Manhattan, where "SNL" originates, was surrounded by hundreds of protesters. 

Of the episode's many weird moments — a sketch featuring Trump shilling his New Jersey chicken-wing restaurant, for example — the show's most memorable sketch was a pre-taped segment in which Trump spasmodically dad-dances in an attempt to mimic Drake's moves in his "Hotline Bling" music video.

Of course, once Trump was elected president and was mercilessly mocked by "SNL" each week, his feelings toward the show chilled considerably. That chill turned into a deep freeze after he lost his re-election bid, and the mockery grew even more pointed. "I once hosted 'Saturday Night Live,' and the ratings were HUUUGE!" Trump wrote in 2022 on his Truth Social platform. "Now, however, the ratings are lower than ever before, and the show will probably be put to 'rest.' It is just not, at these levels, sustainable — A bad show that's not funny or smart ... It was once good, never great, but now, like the Late Night Losers who have lost their audience but have no idea why, it is over for 'SNL' — A great thing for America!"

During a 2015 campaign rally, Donald Trump took a shot at New York Times reporter Serge Kovaleski, who wrote a 2001 article poking holes in Donald Trump's still-unproven claim that he witnessed "thousands" of Muslims in New Jersey celebrating the 9/11 terror attacks. As the video from the rally indicated, Trump decided to make fun of Kovaleski, who has arthrogryposis, a condition in which muscles and joints stiffen.

"Now, the poor guy — you ought to see the guy," Trump said before launching into a disgraceful impression of the reporter's disability. "'Uh, I don't know what I said. I don't remember,'" Trump said, contorting his arms and making silly faces. 

Trump was pilloried for the cruel mockery and responded with a statement to The New York Times claiming that not only did he know nothing about the man he so pointedly degraded, but he was also unaware of his disability. "I have no idea who this reporter, Serge Kovalski [sic] is, what he looks like or his level of intelligence. I don't know if he is J.J. Watt or Muhammad Ali in his prime — or somebody of less athletic or physical ability," Trump said. "If Mr. Kovaleski is handicapped, I would not know because I do not know what he looks like."

One of the lower points of Donald Trump's presidency surrounded his response to a notorious "Unite the Right" rally in Charlottesville, Virginia, in 2017, which turned violent when torch-wielding white supremacists clashed with counter-protesters. "You had some very bad people in that group," Trump said of the white supremacists, as reported by ABC News. "But you also had people that were very fine people on both sides."

Prior to that, however, Trump raised eyebrows during his presidential campaign when he appeared on CNN's "State of the Union" in 2016, and anchor Jake Tapper tried in vain to press him to denounce the Ku Klux Klan after former grand wizard David Duke endorsed Trump. "Just so you understand, I don't know anything about David Duke, okay?" Trump said, claiming to have no knowledge of Duke — arguably America's most notorious white supremacist. 

"I don't know anything about what you're even talking about with white supremacy or white supremacists," Trump continued. "So I don't know. I don't know — did he endorse me, or what's going on? Because I know nothing about David Duke. I know nothing about white supremacists. So you're asking me a question that I'm supposed to be talking about people that I know nothing about."

Among the more head-scratching moments of Donald Trump's presidency was when the press gathered at the White House to watch the president and first lady view a solar eclipse. As cameras click, Trump casts his eyes skyward, leading a voice off-camera (said to be a White House aide) to caution, "Don't look!" Naturally, Trump did what he usually does when told not to do something: he immediately stared at the sky again. 

Finally, he reached into his pocket to pull out a pair of special glasses he'd been given with which to watch, placing them on his face and then looking again. After a few moments, Trump apparently had enough eclipse-viewing, and took the glasses off before giving a thumbs-up to the assembled media. 

Luckily for Trump, it appears he was spared the severe retinal damage that can result from staring directly into the sun. However, the Space.com website viewed the whole thing as a teachable moment, using Trump as an example of how not to view a solar eclipse.

Donald Trump's controversial assertion that he could go up to any woman and kiss her (in addition to grabbing her by the, um, well, you know) without consent apparently didn't stop at humans, but also applied to inanimate objects. That was the case when he took to the stage of the 2020 edition of the Conservative Political Action Conference (CPAC). In a video of that moment, Trump concludes his speech by walking up to a nearby American flag and then giving it a big bear hug. "I love you, baby," he mouths, more than once, before planting a big sloppy kiss on Old Glory. 

That particular moment did not go unnoticed on social media, where Trump's bizarre behavior toward the flag generated numerous wisecracking comments. "This flag is easily the oldest thing Trump has ever sexually assaulted," tweeted comedian Noel Casler. Another comment read, "I will take 'Things Melania Never Says' for $500," while another summed it up best by simply posting a GIF of a baby vomiting. 

What made the moment all the more cringe-worthy was that Trump had pulled the exact same stunt at the previous year's CPAC. 

It's no secret that Donald Trump believes he knows more about everything than anybody. During the COVID-19 pandemic, that included scientists. During an infamous 2020 press conference, Trump began freestyling his own remedies for the coronavirus. Informed that COVID-19 thrives less successfully in sunlight, a tiny lightbulb went off in his head. "So supposing we hit the body with a tremendous — whether it's ultraviolet or just a very powerful light — and I think you said that hasn't been checked because of the testing," Trump said. "And then I said, supposing you brought the light inside the body, which you can do either through the skin or some other way, and I think you said you're going to test that, too."

As ridiculous as that was, Trump's next idea was even wilder. "I see the disinfectant that knocks it out in a minute, one minute," he added. "And is there a way we can do something like that by injection inside or almost a cleaning?"

Perhaps fearing a sudden rash of lawsuits from gullible dimwits following that advice by injecting themselves with cleaning products, the manufacturer of Lysol begged people to ignore Trump. "As a global leader in health and hygiene products, we must be clear that under no circumstance should our disinfectant products be administered into the human body (through injection, ingestion or any other route)," a spokesperson for Reckitt Benckiser, manufacturer of Lysol, said in a statement to NBC News.

There have been many memorable presidential summits, from JFK's Cold War confab with Soviet leader Nikita Khrushchev to Richard Nixon's visit to China to meet with Mao Zedong. For sheer hilarity, however, none of those came close to topping Donald Trump's 2018 Oval Office visit with Kanye West. 

While cameras filmed the entire spectacle, West (accompanied by NFL legend-turned-movie star Jim Brown) was ostensibly there to discuss prison reform and to plead for the freedom of imprisoned ex-gang leader Larry Hoover. West made his case, reported CNN, as only West could. "So there's a theory that — there's infinite amounts of universe and there's alternate universe so it's very important for me to get Hoover out, because in an alternate universe, I am him and I have to go and get him free," West told Trump in what sounded more like a pitch for the next "Doctor Strange" sequel than a clemency plea.

And yes, of course, it got even nuttier, particularly when West spoke out about repealing the 13th amendment — abolishing slavery — which he explained thusly: "If you're building a floor, the constitution is the base of our industry, right, of our country, of our company. Would you build a trap door that if you mess up and you accidentally something happens, you fall and you end up next to the Unabomber?" Trump responded to West's crescendo of crazy by musing, "That was quite something. That was quite something." 

There has been much speculation about Donald Trump's mental state in recent years, and he didn't exactly do himself any favors when he boasted about taking a cognitive test, bragging that he'd "aced" it. That test was revealed to be the Montreal Cognitive Assessment, devised to test whether a person has dementia. "The first questions are very easy," Trump explained in a 2020 TV interview, insisting the test became progressively more difficult, including one that taxed the memory. "Like, you'll go, 'Person, woman, man, camera, TV,'" he said in a manner indicating he was proud to still remember the correct order.

In a subsequent interview with Fox News, Chris Wallace told Trump that he'd taken the test and found it to be a piece of cake. "No, no, no," Trump responded. "It's all misrepresentation," he said. "Because, yes, the first few questions are easy, but I'll bet you couldn't even answer the last five questions. I'll bet you couldn't — they get very hard, the last five questions." 

Wallace called him on it and asked Trump to provide an example of one of those tough questions, to which Trump responded, "I'll get you the test, I'd like to give it. I'll guarantee you that Joe Biden could not answer those questions."

Donald Trump may want to take another shot at that cognitive test, given some of the bizarre pronouncements he's made at his campaign rallies. These have ranged from an obsession with low-flow toilets to the perils of energy-harnessing wind turbines, which he's continually claimed are responsible for the wide-scale massacre of birds  — and also cause cancer. 

During a 2023 rally, Trump sounded the alarm about a whole other danger he attributed to those windmills: killing whales. "They are washing up ashore," said Trump, referring to whales. "You wouldn't see that once a year — now they are coming up on a weekly basis. The windmills are driving them crazy. They are driving the whales, I think, a little batty."

If that claim sounds dubious, it's because it is. "He displays an astonishing lack of knowledge of whales and whale strandings," whale researcher Andrew Read told The Guardian of Trump and his theory. "There is no scientific evidence whatsoever that wind turbines, or surveying for wind turbines, is causing any whale deaths at all."

Cringe-worthy television moments featuring Donald Trump aren't that hard to come by; for proof, simply wait for any of his rallies to end. That's when viewers can experience one of the weirdest spectacles in political history as Trump performs what can charitably be described as a groove-free approximation of dancing to the strains of 1970s disco hit "Y.M.C.A." by The Village People. Each time, Trump purses his lips into a pout, balls his hands into little fists, and executes tiny punches in the air, occasionally in time to the song's rhythm. 

While the dancing itself is odd enough, there's also the cognitive dissonance of Trump boogieing away to a song that's best known as a gay anthem, as lyrics blare about hanging out with all the boys at a place where "they have everything for young men to enjoy."

Trump discussed his appreciation of music, and that song in particular, during a 2022 interview with the Nelk Boys' "Full Send" podcast. "Would you believe it? I love music. I have an aptitude for music," Trump said, as reported by People. "I've always had a high aptitude for music, but I love great music." Meanwhile, Trump insisted that he's well aware of the gay origins of "Y.M.C.A." — but doesn't care. "Did you ever hear that? They call it the gay national anthem," he said. "But 'Y.M.C.A.' gets people up and it gets them moving."