Last month, Donald Trump filed a Federal lawsuit against the New York Times, four of their reporters, and the publisher Penguin Random House. Four days later, a judge threw the suit out over violating a rule on what legal filing should involve. The suit was refiled nearly a month later, with one of the reporters, Michael S. Schmidt, no longer a defendant. The amended complaint also highlights Donald Trump’s sad acting career in trying to show that he was a successful entertainer before appearing on the Apprentice.
His lawyers highlighted a quote about his extreme willingness to make cameo appearances:
“He always played himself and so that was how powerful his brand was . . . Anytime you have a sitcom that needs that stock character, Trump was not only somebody that comes to mind but somebody that’s super willing to do it.” Rebecca Sun, Hollywood Reporter, cited in Inside Edition (May 12, 2016), https://www.youtube.com/watch?v=cbdrr9w4e80 (last visited Oct. 16, 2025).
The cited video doesn’t help their case. At one point in that the narrator says “there [Donald Trump] is with Bo Derek in a movie very few people saw.” And they follow that up by mentioning that “Trump actually won an award, unfortunately it was a Razzie for the year’s worst supporting actor.”
They follow up that with this:
Wrote another commentator: “But politics aside, Trump was famous
for decades prior to entering the political fray, beginning in the 1980s, when he first became a prominent figure as a New York City real estate tycoon.” Michael Kennedy, ScreenRant, Ghosts Can’t Do It: Donald Trump Once Starred in a Supernatural Sex Comedy (April 23, 2020), https://screenrant.com/ghosts-cant-do-it-movie-donald-trump-appearance/ (last visited Oct. 16, 2025).
The cited story is about Donald Trump’s Razzie winning role. The end of the story references the “award”:
He even won a Razzie for his performance, and as was noted then, the worst Razzie is the one someone gets for playing themselves. Whether one loves Trump or hates him, he’s certainly a charismatic presence, but an actor he isn’t.
Later in the filing they choose highlight some of his roles:
Illustrative, non-exhaustive, and publicly available examples of the consistent demand for President Trump in popular culture—before The Apprentice— include: Ghosts Can’t Do It (1989) (playing himself in scenes with Bo Derek); Home Alone 2 (1992) (playing himself in a cameo with Macaulay Culkin); The Fresh Prince of Bel Air (1994) (playing himself in a scene with Will Smith and other cast members); The Little Rascals (1994) (playing the father of one of the characters); The Nanny (1996) (playing himself in a scene with Fran Drescher); The Drew Carey Show (1997) (playing himself in a sketch with Drew Carey); NightMan (1997) (playing a Marvel comics superhero version of himself); Spin City (1998) (playing himself in a scene with famed actor Michael J. Fox); Celebrity (1998) (playing himself in Woody Allen’s comedy); Sex In The City (1998) (playing himself in a scene with Kim Cattrall); Zoolander (2001) (playing himself in opening scene cameo of Ben Stiller’s comedy); Two Weeks Notice (2002) (playing himself in a scene with Hugh Grant); and The Ali G Show (2003)17 (interviewed by Sasha Baron Cohen).
What seems like the most embarrassing example to highlight is his appearance on NightMan. A syndicated superhero TV show that aired for two years. His lawyers described that as him “playing a Marvel comics superhero version of himself.” That is sort of accurate, as the show was based on a comic book character from Malibu Comics and Marvel Comics had acquire Malibu Comics several years before the show. (You can watch his appearance on the show on Tubi, it starts 16 minutes in to the episode.)
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