Donald Trump Just Can't Beat This US President's Hollywood Record

When Donald Trump first swept into power in 2016, he did so on a wave of celebrity glamor that he had cultivated over the course of decades in the public eye. Whereas other, more typical businesspeople might reserve their public appearances to company events and conferences, early in his career, Trump demonstrated that he was interested in expanding his presence beyond the sphere of the real estate industry in which he generated much of his wealth, to turn the Trump organization into a major lifestyle brand based around his own celebrity. But his success in Hollywood didn't come close to another U.S. president — Ronald Reagan.

Over the years, Trump took it upon himself to become a familiar face in the world of entertainment, gaining roles in several movies before pivoting toward the world of reality TV. It may seem surprising that a would-be U.S. president would emerge from the world of entertainment rather than politics, but this isn't the first time this has happened. Reagan, who was elected to the office of U.S. president in 1980 and again in 1984, was also a familiar face to the American public, with an extensive movie career behind him that dwarfs Trump's filmography by comparison.

Ronald Reagan came to Hollywood in the late 1930s, completing a screen test for Warner Brothers Studios after arriving in California with the Chicago Cubs baseball team, for which he provided state radio broadcasts of games. Handsome and affable on screen, he was a notable star of B-movies throughout the 1940s and 1950s, having starred in films made for the army which implied that he had gone overseas to fight (he hadn't, but remained in California making such films).

His charm and standing within the film industry led to him eventually becoming the president of the Screen Actors Guild in 1947, a position he held until 1952. During this time, he controversially served as a witness to the House Un-American Activities Committee which attempted to expunge communist sympathy in the movie industry and elsewhere. Reagan has been a liberal and democrat in his early life, following the sympathies of his father, who deeply admired Franklin Roosevelt and the New Deal. However, as he aged, Reagan became more conservative and by the 1950s, was campaigning for Republican politicians.

In the 1960s, he entered politics himself, framing himself despite his movie star background as an everyman who was sick of the current political landscape in the country. He served as governor of California from 1967 until 1975, and attempted to gain the Republican presidential nomination as early as 1968, by which time he had starred in 53 movies, the last being "The Killers" in 1964.

Despite Donald Trump only truly becoming politically active in the 21st century, he first toyed with politics as early as 1987, when he first began positioning himself as a potential future president who could save America from itself and restore its reputation on the world stage. And as Trump looked to build his personal brand, it wasn't to political forums or political parties he looked, but rather the world of entertainment.

In the decade and a half that followed, Trump appeared in at least 10 feature films, the most high profile of which were "Home Alone 2: Lost in New York," in which he offers directions to Macaulay Culkin's character, Kevin, in a New York hotel, and the Ben Stiller fashion industry comedy "Zoolander." But he also appeared in a number of less well-remembered films, such as the 1989 flop "Ghosts Can't Do It."

In almost every instance, Trump played himself, or at least a character remarkably like himself, and according to insiders who worked with him on movie sets during this time, it seemed Trump would take any part as long as he appeared as Donald Trump. For him, reiterating to the public that he was a rich and successful businessman was the whole point, even if the movie was scripted.

Donald Trump's appearances in scripted movies playing himself worked to reinforce his persona as a larger-than-life business mogul. However, they weren't the only medium in which he was willing to work from the late 1980s onward. Just as Ronald Reagan had remained a regular fixture in people's living rooms in the 1950s by hosting the "General Electric Theater" drama series, Trump made repeated appearances on television to keep his profile high.

Many of these appearances were sitcoms, such as "The Fresh Prince of Bel-Air," "Sex & The City," and "The Nanny," in which he played himself. However, he also gave many TV interviews on shows such as "Larry King Live" in which he made clear his political aspirations during this time. His first attempt at running for president, which happened in 2000 as nominee of the Reform Party, failed. However, one more television feat was to raise his profile even higher. In 2004, he signed on to star in NBC's "The Apprentice," a reality TV show in which he hired, or more likely fired, would-be business people. It was a huge hit, running for 15 seasons until 2017. For many, it was this aspect of his career that really gave Trump the platform from which to reach the White House, positioning himself as a ruthless negotiator who could bring his business acumen to the White House for the benefit of the country.

However, though Donald Trump seemingly had close connections to Hollywood during the 1980s and 1990s and maintains a number of celebrity supporters in the film industry, notably Sylvester Stallone, Mel Gibson, and James Woods. But for the most part, Hollywood and Trump have experienced a major rift after the latter first came to power, with many A-list celebrities coming out in opposition to the Republican and the policies of his administration.

Rosie O'Donnell, Mia Farrow, Richard Gere, and Jane Fonda have all been open about their opposition to Trump's presidency. In September 2025, many more celebrities, including Robert De Niro, Meryl Streep, and Ben Affleck, signed an open letter decrying his handling of comments made by late night host Jimmy Kimmel, who had his show taken off air, in the wake of the assassination of Trump supporter Charlie Kirk.

But characteristically, Trump has gone on the attack, criticizing his celebrity detractors publicly and deriding the American movie industry in messages on his Truth Social platform. As reported by the Los Angeles Times, he has said: "The Movie Industry in America is DYING a very fast death. Hollywood, and many other areas within the U.S.A., are being devastated." His plan to impose 100% tariffs on foreign films has caused even greater division and rattled the movie industry. Whether Trump himself will ever appear in another movie remains to be seen.