Celebrities Who Loved Trump Before He Was President

Trump's Celeb Friends 

Donald Trump has stated:

Oprah was a friend of mine until I ran for public office.

In 1988, Oprah Winfrey and Trump were photographed ringside at the Tyson vs. Holmes fight.

On January 11, 2000, Oprah wrote a letter to Trump saying: “Too bad we’re not running for office. What a team!” The letter has since been published in Trump’s book, Letters to Trump.

Donald Trump's friendship with Michael Jackson, which began in 1988, lasted decades.

Elton John and Donald Trump appeared smiling with Ivana Trump in 1988.

On June 23, 2008, Melania Tump and Heidi Klum gave Trump kisses on the cheek at the Park Avenue Plaza in New York.

In 1999, Alec Baldwin dined with Trump at a New York Gala for breast cancer research.

In 2007, Tina Fey and Alec Baldwin posed with Donald Trump and Melania at the Golden Globes.

Shaquille O’Neal (“Shaq”) attended Trump's wedding to Melania in 2005. On August 20, 2007, they were also photographed together at the 4th Annual Zo's Million Dollar Shootout - Golf Tournament.

On October 18, 2002, Nicky and Paris Hilton were photographed with Trump during rehearsals for the 2001 VH1 Vogue Fashion Awards.

In 2005, Trump appeared on G-Unit radio during a segment featuring 50 Cent, DJ Whoo Kid & Tony Yayo.

In 2012, Anna Wintour warmly greeted Melania as Trump stood smiling at the 2012 Met Gala. In 2005, Donald Trump and Anna Wintour were photographed talking at the U.S. Open in Queens, New York. Trump’s daughter, Ivanka, was photographed talking to Anna Wintour in 2008. Ivanka has publicly spoken about Anna offering her a job without an interview because “she knew I liked fashion.”

On March 9, 2011, Snoop Dogg performed at the Comedy Central Roast Of Donald Trump.

Gayle King attended Trump's wedding to Melania in 2005. On December 1, 2005, Gayle King and Trump posed with Melania at the opening of The Color Purple.

In 2015, Tom Brady told Boston’s WEEI radio station:

[Trump] always gives me a call and different types of motivational speeches at different times. [...] I mean it’s pretty amazing what he’s been able to accomplish. He obviously appeals to a lot of people, and he’s a hell of a lot of fun to play golf with.

On June 25, 2005, Tom Brady and Trump chatted at the Floyd Mayweather vs. Arturo Gatti - WBC Lightweight Title Fight.

On November 4, 1983, Trump and Andy Warhol were photographed together with a polo pony.

On March 15, 1988, Hulk Hogan and Trump posed with Andre the Giant at a press conference announcing "WrestleMania IV".

On April 1, 2014, Donald Trump and Martha Stewart were photographed together at The New York Observer Relaunch Event. On June 11, 2012, Trump and Martha Stewart were pictured together at Richard "Skip" Bronson's "The War at the Shore" Book Publication Party.

On February 11, 2003, Ja Rule and Trump were photographed at a launch party for the book, 'Backstage Sexy' at Spice Market.

Barbara Walters attended Trump's wedding to Melania in 2005. Barbara Walters also attended the wedding of Trump's daughter, Ivanka Trump, to Jared Kushner on October 25, 2009.

On Dec. 12, 1987, Don King, Barbara Walters, and Trump posed for a photograph.

PDiddy (Sean Combs, “Puff Daddy”) attended Trump's wedding to Melania in 2005. In a 2015 Washington Post interview, PDiddy said that he "always liked Donald's style," admired his work ethic, and that the two are friends.

On March 10, 2013, Tiger Woods and Trump posed with the Gene Serazen Cup after Woods won the Cadillac Championship golf tournament.

Katie Couric attended Trump's wedding to Melania in 2005. Katie Couric and Trump were photographed with Melania at The Entertainment Industry Foundation's 2nd Hollywood Hits Broadway Benefit Gala for Colon Cancer, held April 24, 2004.

On May 19, 1997, Donald Trump and Aretha Franklin attended the grand opening of Trump International Hotel and Tower.

Trump and the Reverend Al Sharpton, described as "the ultimate New York frenemies" by The New York Times, were photographed at Trump World Tower in 2006.

Writing on his Cyber Dust app in 2015, Mark Cuban said:

I don't care if he says the wrong thing. He says what's on his mind. He gives honest answers rather than prepared answers. This is more important than anything any candidate has done in years. [...] Now maybe we will accept candidates warts and all and look at what they can do rather than what headlines they create. Congrats Donald.

On June 3, 2009, Mark Cuban posed with Trump and Donald Trump, Jr. at Trump Towers.

Trump and the Reverend Jesse Jackson were photographed giving the "thumbs up" during a Trump Plaza party before the Tyson-Spinks title fight in 1988.

Jeff Zucker, the President of CNN from 2013-2022, attended Trump's wedding to Melania in 2005. On October 1, 2008, Jeff Zucker and Trump were photographed at the 'Green Goes with Everything' event held at Loeb Boathouse.

On February 27, 2004, Trump appeared with Ellen DeGeneres on "The Ellen Show."

Trump's TV & Movie Cameos

In 1999, Trump made a cameo in Sex & the City (Season 2, Episode 8) with Sarah Jessica Parker (“Carrie”) narrating: “Samanatha, a Cosmopolitan, and Donald Trump. You just don’t get more New York than that.”

Trump also appeared on a number of movies and TV shows, including The Fresh Prince of Bel-Air (1994), Spin City, Home Alone 2 (1992), The Little Rascals (1994), The Nanny (1996), Bobby Brown even featured him in his 1989 music video “On Our Own.”