Trump Rants About Emmy Losses, Touts His Singing Voice, and Fixates on ‘Will and Grace’ Actors

In his new book, Apprentice in Wonderland: How Donald Trump and Mark Burnett Took America Through the Looking Glass, Variety’s Co-Editor-in-Chief Ramin Setoodeh took a deep dive into the reality TV career that made Donald Trump, more than just a failed casino owner and real-estate developer but a bonafide television star.  For his deeply reported and revealing look at the pivotal moment in the former President’s career, Setoodeh interviewed Trump six times between 2021 and 2023 and talked to a wide swathe of the industry professionals and celebrities all circling the show’s orbit. In this exclusive excerpt, Setoodeh looks at Trump’s first Emmy nomination and his bizarre obsession with the NBC show Will and Grace and its star Debra Messing.

Donald Trump may remember his first Emmy nomination more clearly than his first nomination for the presidency. The summer after Season 1 of The Apprentice aired, he received good news from his producing partner. “I got a call from Mark Burnett,” Trump says. “He said, ‘Congratulations — you were nominated for an Emmy!’ He said, ‘You should win.’ I had the hottest show in many years.” His voice is steady as he says this, but his head bounces like one of the Trump bobblehead dolls that became a ubiquitous accessory during his presidency. Watching this in person is mesmerizing: Trump jolting his head around is the Donald equivalent of a parrot puffing up its feathers in a display of dominance.

Trump was nominated as an executive producer of The Apprentice in the newly added category of outstanding reality-competition series — an acknowledgment of the genre’s success that the Emmys had added for the first time only the year before. In 2003, the trophy had gone to The Amazing Race, the CBS series that sent contestants on a globe-trotting adventure with an army of quick-moving producers and camera operators. In 2004, The Amazing Race was a heavy favorite once again, and indeed it eventually beat The Apprentice (as well as American Idol, Last Comic Standing, and Survivor), continuing what would eventually be, to Trump’s great displeasure, a seven-year winning streak for the CBS show.

“I thought I’d win too,” Trump says, still looking disappointed all these years later. He gives himself a pep talk. “But I killed The Amazing Race in ratings,” Trump says. “I’d never even heard of the show. I knew it was done by all of Hollywood royalty. They had many producers. I think even Harvey Weinstein was there. They had all the biggest people in Hollywood.” Trump’s gift for mudslinging is not rooted in accuracy, even when reliving the years he remembers most fondly. Weinstein produced another popular reality TV series, Project Runway, but the disgraced mogul had nothing to do with The Amazing Race. (Although the Top Gun producer Jerry Bruckheimer did have an executive producer credit.)

Trump assumed that his name would be called when the envelope was cracked open. “I really deserved it,” he says. “I had the highest ratings. It was the talk of the whole country — beyond, even.” Trump had already taken the stage earlier that evening with another reality TV royal, Simon Cowell from American Idol, to present the award for best supporting actress in a comedy series. “Okay, and the Emmy goes to . . . ,” Trump said as he tilted the envelope, taking up the spotlight from a grinning Cowell, “Cynthia Nixon, Sex and the City.” It was the final season of the beloved HBO series, and Miranda’s win over the fan favorite, Samantha (played by Kim Cattrall), was something of a shock. (“Do I wish I had gotten my Emmy from somebody else?” Nixon would say in 2017. “Yes, I do. Absolutely I do. But it’s not like he picked me. He just passed off the trophy.”)

But the surprise that some viewers felt in that moment was no match for Trump’s bewilderment at going home empty-handed. During his category, Trump had already proclaimed himself the winner in his head. “And I stood up to start walking down the aisle,” Trump recalls. “They said, ‘The winner is . . . The Amazing Race.’ I said, ‘Oh shit!’ And I sat down.” He remembers that one of his seatmates, Howard Stringer — who’d soon be named the CEO of Sony Corporation — turned to him and said, “Donald, you got screwed!”

“And Amazing Race kept winning it, winning it,” Trump says with disdain. “American Idol was so powerful at the time. It was not fair that every year it was The Amazing Race. It was nothing special!” He’s suddenly handicapping decades-old Emmy ceremonies like political races, sounding off with the passion of a cable news host waiting for the vote count in the Rust Belt to come in. “I said, ‘I can’t believe it! Amazing Race won again?’ Honestly, it was a joke. They shouldn’t have won over me.”

In dissecting the awards show results, Trump borrows a term he’s frequently heard about himself on Fox News. “But it was pure establishment,” Trump says of the relatively scrappy Amazing Race, in which contestants slept on airport floors to get ahead in the game. “And I was anti-establishment. And Mark was anti-establishment too.” He pauses and realizes that this assessment isn’t quite right. “Mark is pretty establishment,” he concedes, “but Mark Burnett was not establishment at the time.”

This analysis doesn’t make much sense, and it doesn’t need to. Trump’s messaging — that he was somehow burned by corrupt forces out of his control — is a familiar page from his conspiracy theory handbook. After The Apprentice premiered, in his new life as an entertainer, Trump breathed in the exclusive air of A-list fame. The new attention he received as a businessman and as a celebrity padded his ego beyond its already inflated size. As a young man, Trump couldn’t summon the courage to pursue his dream career as a film producer, and so went into the family business. But Trump had, at age fifty-eight, found his voice — and his true calling — in stardom.

“It’s a very rare thing that a show is successful,” Trump tells me one afternoon, circling back to one of his favorite subjects: his own on-camera charisma. “I used to have the stats on that.” Rather than pump himself up, on this particular day in the fall of 2023, shortly before he’d decide to take the stand in a New York City court for his civil fraud trial, Trump is uncharacteristically reserved about putting his TV chops front and center.

Instead, he rattles off some statistics without citing any particular source: “I think 10 percent of the shows make it, 5 percent are successful, 1 percent are very successful. That sounds like Broadway odds, right?”

The Apprentice maximized Trump’s footprint all over America, and the country hung on his every word — including his attempt to carry a tune in front of millions of people. When Trump was nominated for another Emmy the following year, in 2005, the Emmys producers asked him if he’d participate in a contest called “Emmy Idol.” Playing off American Idol, a juggernaut much bigger than The Apprentice, the Emmys recruited several TV stars to compete by belting out popular theme songs, with the viewers asked to vote on the best act.

Trump was up for anything, as long as a stage was involved. So he agreed to dress up as the character on Green Acres played by Eddie Albert, a farmer in denim overalls, and carry a rake during his turn — crooning the show’s theme song. Trump’s duet partner was Megan Mullally, the comedian best known for playing the shrieking millionaire Karen Walker on Will & Grace, who channeled the Hungarian princess Lisa Douglas (played by Eva Gabor) in a green suit with a fur collar. Ellen DeGeneres, the Emmys host that year, could barely contain her smirk as she introduced the duo. Trump and Mullally charmingly belted out their tribute to the popular 1960s sitcom — the Schitt’s Creek of its time — about a couple that leaves their Manhattan luxuries behind for rough farm living. Mullally laughed through Trump’s opening verse, which he kept largely on key, though without much of a sense of rhythm.

“I didn’t know her,” Trump says of Mullally, “but she was the star of the show.” And to Trump, that’s all that mattered. Mullally scored brownie points for switching one of the song’s lyrics — where her penthouse-living wife lists the indispensable perks of city life — from “Times Square” to “Trump Tower,” which had become just as important a landmark to those watching at home.

“They said, ‘Would you participate in a skit?’ They came in with stuff. I said, ‘All right, I’ll do it. So I did it.’ William Shatner did it. Other people did it, very well known. Who are they?” Trump stumbles, admitting he can’t remember. “You’ll figure it out.” (The other contestants included Kristen Bell, who sang the song to Fame; Macy Gray and Gary Dourdan, with “Movin’ On Up” from The Jeffersons; and Shatner, who warbled the title sequence of Star Trek with the opera singer Frederica von Stade.)

Trump might have lost the Emmy again to The Amazing Race that night, but he still takes pride in his consolation prize — that the viewers voted for his performance as the night’s best, beating out the other three acts. He asks to go off the record, as if he were about to reveal national security secrets, to brag about the percentage of the vote that he allegedly received.

“But at the end of the evening, I won with a massive — it was some- thing like . . . ,” he says, giving me a number, not for publication. “I got almost all the votes. I sang ‘Green Acres,’ and I was dressed in overalls and a straw hat.” He clarifies that he didn’t need to take singing lessons to prepare. “No, no, no,” he says. “But I have an aptitude for music.”

Trump’s love of Broadway musicals — especially Evita — stems from what he believes is a natural gift. Trump doesn’t usually volunteer detailed stories about his childhood, but here he makes an exception. “You know, when I was young, my parents took me to a place, and they said, ‘What’s up with this guy? We think he’s really smart!’” He’s referring to himself. “They gave me all these tests. And I’ll never forget, they told my father, ‘Your son has an unbelievable aptitude in music.’ Like they play a note . . .” To make this story come to life, Trump offers his own sound effects. “. . . Ding, ding!”

He continues: “And then they play it again. And then twenty minutes later, they asked, ‘Which is the note we first played?’” The sound effects return from Trump’s own lips: “Ding. Ding. Ding.” It was, in Trump’s telling, an early marker of his genius. “They said, ‘He has an aptitude in music.’ Anyway, so I did ‘Green Acres.’ I’m telling you, we brought the house down. You have the clips of it?”

Trump’s face lights up as he presses me for a favorable review of his singing skills. “Do you agree?” he asks me. “It brought the house down.” He then starts to wonder about his partner. “How has Megan Mullally treated me over the years? Do you have any idea?” He twitches suspiciously, eager to add another name to his lengthy Hollywood enemies list. “I know she loved her time up on the stage,” Trump says about Mullally. “She loved doing it. We rehearsed the day before, and she said the same thing: ‘You have a great feel for the music, the song.’ Anyway, I did the song, brought the whole house down, and they voted.” And this time, Trump won the popular vote.

Trump is jubilant that he managed to outperform the star of Veronica Mars in a TV singing contest. He even revisits how fun it was to resurface his brief turn as a singer on social media from the White House. On December 20, 2018, Trump tweeted out the Emmys clip, saying, “Farm bill signing in 15 minutes! #Emmys.” (Mullally, an outspoken Democrat, tweeted back “omg” and then: “if you guys need me, i’ll be in a hole in the ground” with a dead face, skull, and goodbye emoji.)

What inspired Trump, as the president of the United States, to re-claim past glories, to remind the American public of this kitschy moment? “Somebody gave me the idea,” Trump says, vaguely. “What a great idea! We passed legislation.” Trump doesn’t dwell on the specifics of the bill, which offered $867 billion in aid to farmers and legalized the production of hemp. “And that was a sensation.”

Trump says when he tweeted out the clip, “that thing had hundreds of thousands of hits. And the farmers liked me, and I won the farmers both times by a lot.” From Trump’s vantage point, all of his enemies — from the deal makers in Congress to the producers of The Amazing Race — are no match for his gift-from-the-heavens voice. He’s on such a high, he can’t resist telling me his favorite lie. “I won both elections, by the way,” Trump says. “By a lot!”

EVEN NOW, after all his years in the spotlight, Trump struggles to contend with one of the downsides of fame — his haters. And one particular facet of Trump’s unique sort of stardom is that many of his critics are among those he most wants to court: other celebrities. Many of the Hollywood pals first cultivated during his Apprentice years would later turn on him as president, which of course remains one of his biggest fixations. Here, in his Trump Tower aerie far above New York City, his enemies from the entertainment industry still occupy his thoughts around the clock. It’s as if he were being jabbed by a pebble in his loafers all day long.

Take his obsession with Debra Messing, another actress from Will & Grace who figured prominently in his past. Trump still remembers the day he met Messing — who played the self-centered New York interior designer Grace Adler on NBC — around the time of The Apprentice’s second season. “So I’m in line,” Trump recalls. “The show had gone to No. 1, and we’re ready to do the upfronts, which I’d never heard of.” As a new TV star, he was quickly catching up with Hollywood jargon: upfronts are an annual presentation that networks give in May, trotting out their stars to charm advertisers ahead of the upcoming TV season. “And Debra Messing came up to me. She had a show at a similar time.”

He doesn’t seem able to say the title Will & Grace — but then again does he need to? Messing’s sitcom remains widely remembered and even beloved years after its first incarnation left the air. (It returned, first with a 2016 viral clip of the characters endorsing Hillary Clinton for president and then with a #Resistance-ready reboot in 2017. The first episode featured Messing’s character repulsed that she’s been hired to redesign Trump’s Oval Office. She ends up leaving a “Make America Gay Again” cap on his desk.) In its heyday, the series was part of the Must See TV block of programming on NBC that led into The Apprentice on Thursday nights. More notably, it was an Emmy-winning, groundbreaking smash hit. Joe Biden, announcing his support for gay marriage in 2012, cited the show as priming America to accept same-sex couples, although its true emotional heart lay in its depiction of a platonic, loving relationship between a single gay man (Eric McCormack) and his best friend (Messing).

“She came up to me with her beautiful red hair,” Trump says about Messing, pausing on this detail a beat too long. “And she said, ‘Sir — I love you! Thank God for you! You’re saving the network, and you’re saving my show.’ Because in that world, which I know a lot about now, when you have a hit, a lead-in, it’s a massive difference.” I point out to Trump that Will & Grace came on before The Apprentice, which would mean that it wouldn’t have received a ratings bump from viewers tuning in to The Apprentice. “A lead-in — or a lead out,” he clarifies.

“She was so thankful,” Trump says. “She said, ‘I can’t thank you enough.’ Do you believe this? I’ve been watching her. And I’m saying, ‘She’d do anything for me.’” As he makes this claim, Trump’s words are lathered with a suggestive grease, similar in tone to his boasting about women finding him irresistible in the leaked Access Hollywood tape. (“I’m automatically attracted to beautiful — I just start kissing them. It’s like a magnet. Just kiss.”)

“She was so effusive,” Trump concludes. “And when I see the hatred coming out of her mouth today, it’s incredible.”

On Twitter, throughout his campaign and first term as president, Messing had been one of the most vocal actors bashing Trump. She once called him “a weak, scared, stupid, inept, negligent, vindictive, narcissistic criminal.” When Trump was set to attend a Beverly Hills fundraiser in late August 2019, Messing tweeted, “Please print a list of all attendees please. The public has a right to know.” With a possible category 3 hurricane making its way to Florida, Trump’s attention instead lay with his onetime network-mate. He shot back at Messing on September 5, 2019, venting on Twitter, “Bad ‘actress’ Debra the Mess Messing is in hot water. She wants to create a ‘Blacklist’ of Trump supporters, & is being accused of McCarthyism.” Trump then suggested Messing was racist, without providing any details. “If Roseanne Barr said what she did,” Trump claimed on Twitter, “even being on a much higher rated show, she would have been thrown off television.” (Barr, a Trump supporter, had already been fired from her eponymous sitcom on ABC in May 2018 for making a racist remark about the former Obama White House adviser Valerie Jarrett.)

Here in New York, during his early months outside the White House, Trump hasn’t moved on. Messing is on his traitors list, and he can’t shake the hypocrisy — in his mind — that she once supported him as a reality TV star. “She probably wouldn’t even admit it,” Trump says about Messing’s supposed flattery from more than fifteen years ago. “She came up to me in front of a group of people. I’ve never seen it. She was begging for acceptance!” He takes on a higher-pitched voice that’s supposed to be Messing: “Thank you so much for what you’ve done for me, my show, and for NBC. It will never be forgotten.”

Trump pauses dramatically. “Well,” he proclaims, “it was forgotten. She was just a nasty person. Her and many others. So many people have come up to me over the years and said, ‘Thank you!’ Once I ran for office, that stopped.”

The next time we talk, Trump brings up Messing again, and he confirms something that he’d only dropped hints about in our last meeting. During the early years of The Apprentice, Trump even had a crush on Will & Grace’s leading lady. Maybe that’s why he can’t quite shake the bitterness that now exists between them. A former president who can’t win over a star almost sounds like the premise of a corny romantic comedy, but for Trump, Messing’s rejection is still a sharp dagger to his heart. “This Debra Messing, who I always thought was quite attractive — not that it matters, of course . . .” Their squabbles on social media continue to live rent-free in his mind. “Debra Messing was so thankful,” he says. “And then I watch her today, and it’s like she’s a raving mess.”

Then he starts to quiz me about whether or not Megan Mullally ever betrayed him. As he comes up empty on that front — clearing her of any backstabbing behavior for now — he finally says, “You should tell that Debra Messing story. To me, it’s disgusting.”

From the book Apprentice in Wonderland: How Donald Trump and Mark Burnett Took America Through the Looking Glass by Ramin Setoodeh. Copyright © 2024 by Ramin Setoodeh. Excerpted by permission of Harper, an imprint of HarperCollins Publishers.