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The evolution of Donald Trump: A YouTube investigation

Watch and learn.


Kevin Collier


Posted on Aug 18, 2015   Updated on May 28, 2021, 3:39 am CDT

The Donald wasn’t always this way.

Real-estate mogul Donald Trump, now a controversial presidential candidate, has for years been a mainstay of American pop culture.

While everyone outside the expanding Trump bubble gazes in awe that he’s able to maintain a lead in the Republican primaries—despite calling Mexicans immigrants “rapists,” apparently making a period joke about Fox News host host Megyn Kelly who challenged him during the first GOP debate, and mocking Senator John McCain (R-Ariz.) for being captured fighting in Vietnam, it’s helpful to see how Trump’s public persona evolved.

He speaks mostly of being in business, and he is almost humble, in a still-admitting-he’s-insanely-wealthy way. 

Thankfully, he was a mainstay of television and movies and commercials, much of which has been preserved on YouTube. He was always confident, always focused on business, but he had not yet evolved into the big, loud personality he is today, nor did he always appear so far from getting the joke.

Below, we’ve prepared a collection of 25 clips that show the evolution and strange directions that the persona of the Donald has taken over the years. (It also shows some of the times he was in ridiculous sitcoms and commercials.) We’ll start with a documentary from when a 37-year-old Trump (now 69) bought a team in the now-defunct United States Football League.


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It’s impossible to imagine any professional football league challenging the National Football League. But 30 years ago, the NFL faced a major challenger in the USFL, the United States Football League. 

Trump bought influence in the league with his team, the New Jersey Generals, and was known as one of the key USFL figures pushing to compete directly with the NFL by holding its own fall season. It lost that battle—Trump is widely blamed for its failure—and the USFL fell apart after its third season.


In a 1987 interview with David Letterman, Trump is borderline self-deprecating and definitely wryly funny. He speaks mostly of being in business, and he is almost humble, in a still-admitting-he’s-insanely-wealthy way. Can you imagine the Trump of 2015 saying “I don’t like to think of myself as driven. I don’t like to think of myself, really, as ambitious; I just enjoy what I do”? He’s so diplomatic that Letterman actually says “You act like you’re running for something.”


In 1988, a 27-years-younger Larry King interviewed a 27-years-younger Donald Trump after the Republican National Convention, during which the party officially endorsed then-Vice President and eventual winner George H.W. Bush. Trump is far more subdued here, though he clearly still has the patter and self-confidence he employs now. Even then, he reveled his persona of being a rich businessman who resonates with the working class.

This was the first year, it’s worth noting, that Trump’s Historical Atlantic City Convention Hall served as the venue for a major professional wrestling event, Wrestlemania IV. This gave rise to Hulk Hogan’s immortal pre-match quote, “Thank God Donald Trump’s a Hulkamaniac!”


Trump’s brand as a peak late-80s entrepreneur is so strong that Milton Bradley created a real estate board game called simply “Trump: the Game.” Its tagline is simple yet confusing: “It’s not what you win or lose, it’s whether you win.” The game box includes the teaser text “I’m back and you’re fired,” indicating that phrase was associated with him at least in 15 years before it was his catchphrase on The Apprentice.

As a bonus, this year saw the debut of the Tour de Trump, the Donald’s attempt to create a rival to the Tour de France, but named after himself.


By 1990, in another interview with King, Trump’s not in a great place with his life. His wife, Ivana, hadn’t filed for divorce, but it seems clear the relationship was on the way out. (They would file for divorce two years later.) Business was bad; this was around the time that Forbes reported that he’d fallen from a $1.7 billion net worth to $500 million, and the magazine dropped him from their list of the richest people in the world.

Here, Trump displayed his calmer demeanor, but he was using some of the dominating language and big claims he’s known for today. Newspapers create blatantly false headlines and quotes about him, he said, and they tell his staffers that the only reason they don’t fact-check with him first is because they know he’d tell them they’re wrong. You see one of his open-ended vague bullying claims: “I’d really love to be able to knock a couple of ‘em out.”


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Trump polishes his political-business cred by testiying before the House Budget Committee. Is this a hint of what Trump would be like in elected office? He’s still calm, but borne to hyperbole, saying that the recession of the 1990s was a bona fide “depression.”


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Looking very much like a political candidate, Trump stages a visit to Dalton, Georgia, near the home of his then-fiancée, Marla Maples, for a charity event. The couple would marry the next year, then divorce in 1999.


Trump the casino owner pushes the New Jersey legislature to enable sports betting. “It’s vital for putting the bookies out of business,” he says.


In one of his very few IMDB credits in which he doesn’t play himself, Trump played Waldo’s Dad in the remake of the movie Little Rascals. His scenes aren’t readily available on YouTube, but you can see him here in the credits.


Donald and Ivana star in a Pizza Hut commercial.


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Would-be nemeses Trump and Rosie O’Donnell—yes, you read that right—guest star on The Nanny, though they’re not in the same scenes. Trump has but a few lines, and he basically served as a surprise associate of Fran’s to illustrate how famous she’d suddenly become.


Visiting The Oprah Winfrey Show to tout an op-ed on foreign policy, Trump starts really sounding like a politician. Already he speaks of foreign policy in the no-nonsense, that’s-probably-not-how-diplomats-should-talk sense he does today. (“If you ever go to Japan right now and try to sell something, forget about it.” “The poorest person in Kuwait? They live like kings.”) Still, he denies that he’d run for office. When Oprah asks if he’d consider it, he simply says “Not really.”


There are few people who embody Trump’s passions of bold claims, politics, professional wrestling like former WWE Hall of Famer and Minnesota Gov. Jesse “The Body” Ventura. Trump was at the time very clearly interested Ventura’s reform party.


Here’s the welcome video from in 2000. A skeleton of the original website is still available here.


Two days after 9/11, a German TV station interviewed Trump. He’s moved by the tragedy, but he still acted the selfish-businessman part. His first answer? “I have a lot of property down there, but it was unfortunately affected by what happened to the World Trade Center,” he said.


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Trump does a quick stint on Sasha Baron Cohen’s Da Ali G Show. Like most guests, he’s clearly quite annoyed with the host character. Nine years later, he claimed on Twitter that he wasn’t really fooled.


Trump starts his successful reality show, The Apprentice. His catchphrase is “you’re fired.” America loved it, and it made for a good Onion headline.


Trump’s inexplicable feud with Rosie O’Donnell has no place in any healthy psyche, and should not be consumed by anyone. But it’s a major part what made each of them into the pop-culture figures they are today.


Fun fact: Trump was a major character in Wrestlemania 23, the “Battle of the Billionaires.”


Trump does a infomercial for a book he’s coauthored with Robert Kiyosaki, the author of blockbuster bestseller Rich Dad, Poor Dad series.


This was one of the many years in which Trump repeatedly claimed President Barack Obama had not actually released his birth certificate and was possibly not actually a U.S. citizen who had instead secretly been born in Kenya.

2011 (NSFW)

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Trump agrees to a Comedy Central Roast. Watch and learn.


Trump publishes a series of short dispatches from his desk to his official YouTube account. Per his style at this time, he names the celebrities whose actions he approves of and contrasts them with those with whom he disapproves. Good times.


Trump is inducted into the WWE Hall of Fame.


The first thing Trump did as a 2016 presidential candidate was glide smoothly down an escalator. In his subsequent speech, he effectively says that some Mexicans who come to the U.S. are “rapists.” He stands by his comments, and his position in the polls continues to rise.

Photo via Danny P. Zaprocfov/YouTube | Remix by Jason Reed

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*First Published: Aug 18, 2015, 10:47 am CDT