During the 2016 election, various comic artists satirized Trump and his campaign. For example, following Pepe the Frog's association to the Trump campaign and the alt-right, Matt Furie published a satirical take of his appropriation on The Nib.
In July 1988, Trump and Ted Turner announced plans for a $3 million television film that would depict Trump's life from his childhood to the present day. Trump would have final approval of the actors who would portray him and his wife Ivana Trump, as well as approval of the script, which would be based on his book The Art of the Deal. Trump planned to donate the profits from the film to charity. Filming was to begin in 1989, with its premiere planned for TNT. In July 1991, Scott Sassa, the president of Turner Entertainment Networks, said the film was unlikely to be made in the near future: "Donald is kind of a fluid target right now. So I don't think that one's going to happen. We haven't made an official announcement about it, but I think every time you pick up the paper the story kind of changes."
Another film, Trump: What's The Deal?, was screened twice in New York in July 1991, but was not publicly released until it became available on the Internet in 2015. In 2005, ABC aired Trump Unauthorized, a biographical television film starring Justin Louis as Trump. Although Trump was not involved with the film, he considered it a "great compliment", despite previously threatening to sue the filmmakers if it contained inaccuracies.
You've Been Trumped (2011), a documentary film by Anthony Baxter, follows Trump's efforts to develop a Scottish golf resort. When it was announced that the documentary was to premiere on BBC Two television in the UK, on October 21, 2012, Trump's lawyers contacted the BBC to demand that the film should not be shown, saying that it was defamatory and misleading. The screening went ahead, with the BBC defending the decision and stating that Trump had refused the opportunity to take part in the film. He appeared with Rudy Giuliani in his documentary Giuliani Time.
Since the 1980s, Donald Trump's wealth and lifestyle have been a fixture of hip hop lyrics, his name being quoted by more than 50 artists.
In 2011, rapper Mac Miller released his "Donald Trump" song about rising to Trump-level riches, which became a Billboard hit. The billionaire subsequently requested royalties for using his name, starting a feud with Miller.
Describing the March 2000 The Simpsons episode "Bart to the Future" as "a warning to America", writer Dan Greaney said in March 2016: "What we needed was for Lisa to have problems beyond her fixing, that everything went as bad as it possibly could, and that's why we had Trump be president before her. That just seemed like the logical last stop before hitting bottom. It was consistent with the vision of America going insane". In an interview with TMZ on May 2016, Matt Groening thought that it was unlikely that Donald Trump will become the president of the United States. After Donald Trump won the 2016 election, the Simpsons used the phrase "Being Right Sucks" in a chalkboard gag for the episode "Havana Wild Weekend".
In April 2011, Trump attended the White House Correspondents' Dinner, featuring comedian Seth Meyers. President Barack Obama used the occasion to present several prepared jokes mocking Trump. Retrospectively, Trump claimed "I didn't feel humiliated, I had a great time. So the press is very dishonest, they don't report the truth and therefore it's just easier not to go."
On The Late Show with Stephen Colbert, Stephen Colbert frequently features a caricature of Trump, called "Cartoon Donald Trump". Colbert's reasoning for including a cartoon version of Trump is because he felt like that Trump had resorted to "almost cartoonish tactics". Meanwhile, on Jimmy Kimmel Live!, host Jimmy Kimmel wrote two Dr. Seuss-like books: Winners aren't Losers and its sequel Winners Still Aren't Losers. Both of these books were featured when Trump was the guest star. On the show, Kimmel would read it out loud to Trump, having Trump read the last word on both occasions.
Vic Berger, a frequent collaborator for the comedy duo Tim & Eric, created a series of Trump related videos for Super Deluxe. Each of these videos remix various Trump debate appearances with air horns and crowds chanting Trump's name.
In November 1998, Showtime announced plans for a weekly soap opera to be titled Trump Tower, starring Trump as himself. The series was not produced. In April 2008, Lifetime announced that it would produce the soap opera, which would be executive produced and narrated by Trump. Lifetime president Susanne Daniels said, "Think 'Desperate Housewives' in Trump Tower with the Donald narrating, and you get the idea of what we're after." This version of Trump Tower, to be set in a fictional penthouse located at Trump Tower in Manhattan, was also never produced.
In October 2004, Trump was planning a drama series tentatively titled The Towers, for which he would serve as executive producer. Gay Walch, who was hired to write the series, said that it would have been a "West Wing-type family drama," and that it would have been inspired by Trump's life and career. The lead character would be named John Barron, a pseudonym that Trump sometimes used. The character would have a divorced wife and several adult children who worked with him at a large real estate corporation. The series would focus on Barron's quest to construct the tallest building in the world. Walch read each of Trump's books for research to create the John Barron character, and said that most of the show material came from her, but noted that Trump paid close attention during their meeting. Afterwards, Trump chose to have the character's surname changed to Barron. The series was never produced.
In 2016, Trump remained open to the possibility of airing the series some day, but noted that he would not have time for it if he became elected as U.S. president, while also stating that "it wouldn't be appropriate" for him to be involved with the series as president.
In October 2006, Michael Jacobson, the chief executive officer of Premiere Publishing Group – which published Trump Magazine – announced plans for an animated series based on Trump and his executives. Jacobson planned to have two shorts and a pilot produced within 90 days so they could be presented to Trump for approval, with production projected to begin in the first quarter of 2007.
Jacobson had purchased the rights to an animated Trump series from business associate Mitchell Schultz, who said that "the way to create immortality for Donald Trump is through the youth of America." The series was tentatively titled Trump Takeover. Schultz developed plot lines for the series with Louis Cimino, a friend and writer. In February 2007, Trump hired Animation Dimensions to handle production of the series. Animation Dimensions was to create a pilot for the series, which Premiere Publishing would then present to television networks for consideration. The series never aired.
Trump's hairstyle has been mentioned frequently by the media. His hairstyle has been described as a comb-over, although there is no evidence that Trump has been hiding a bald spot and he has maintained a similar hairstyle since the 1970s.
In 2004, the Chicago Tribune wrote that Trump is "known for his gaudy casinos and unusual mane of copper hair."David Letterman made a joke about Trump's hair in 2008, likening it to a chihuahua. During a 2011 interview with Rolling Stone, Trump said, "I get a lot of credit for comb-overs. But it's not really a comb-over. It's sort of a little bit forward and back. I've combed it the same way for years. Same thing, every time." A gallery of photographs depicting Trump's hairstyle across four decades was published in 2015. In various late-night talk shows and interviews, Trump's hair has humorously been suggested to be a wig, so he has let the interviewers touch his hair to verify its authenticity.