President Donald Trump met an awkward silence when he used a speech that was supposed to celebrate press freedom to attack a female reporter and liken her to a transgender influencer.

Appearing at the redo of the White House Correspondents' Dinner on Friday, Trump hit out at CNN star Kaitlan Collins after she won an award for her coverage of Ukraine President Volodymyr Zelensky's visit to the Oval Office.

This year's dinner was the first Trump had attended since 2015, after more than a decade of boycotts.

But about 10 minutes into his speech, the 80-year-old president mocked Collins, telling the audience: "I want to personally congratulate CNN's Kaitlan Collins on receiving her award. It was all about me. It was a fake, she shouldn't get the award, it was a fake. But I didn't mind. I said, 'Kaitlan, congratulations.' But it was fake, there's no question about it.

"But she's a young, attractive woman," Trump added, as some people in the audience grimaced.

"She never smiles. I said, 'Kaitlan do you ever smile? Smile!' You have a nice position; you're at CNN fake news. You should be a happy person. So smile, Kaitlan! Just smile."

Trump then went on to suggest Collins looked like transgender influencer Dylan Mulvaney, who prompted a Bud Light backlash a few years ago when she appeared in an ad for the popular beer.

"I thought Kaitlan had really made it big with a major new sponsorship," Trump said. "But then I informed her that it wasn't her on the Bud Light can, it was Dylan Mulvaney."

The dinner took place three months after the original event was derailed in April by a gunman who breached security in a bid to assassinate the president.

Trump aides and Cabinet secretaries attended, including Defense Secretary Pete Hegseth, Health Secretary Robert F. Kennedy Jr., and White House Deputy Chief of Staff Stephen Miller.

However, first lady Melania Trump, Vice President JD Vance and Secretary of State Marco Rubio were absent due to scheduling conflicts, according to the White House.

The dinner has long occupied a peculiar place in Washington: part celebration of the First Amendment, part networking event, and part roast.

The president kicked things off by declaring that the roast he had planned to give in April would have been even more of "a doozy" and a "ripping" of the media.

But over the course of about an hour, he nonetheless took aim at everyone from CNN's Jake Tapper ("it only took him one year to break the story that Joe Biden might have suffered from cognitive decline"), commentator Don Lemon ("he has the lowest ratings and the lowest IQ"), and MSNBC's Lawrence O'Donnell ("I never thought he had any talent").

The president's jokes often fell flat, with many of the 700 guests in the room checking their phones as he launched his assaults.

One of his better received gags involved calls for fixed term limits in Congress—something that several Republicans have also called for in the wake of Senator Mitch McConnell's prolonged absence.

"All joking aside, I do think we need term limits in Congress," he said, regaling a story a senator had told him about his partner.

"The other day, a senator I knew got a text… 'When you get home, I want to have you immediately come up the stairs and make love to me.' And he said, 'I can't do both!"

Earlier in the night, the president was forced to endure a video roasting him about press freedom and America being a country of "no kings."

Things became even more awkward when The Wall Street Journal was celebrated for reporting on a lewd letter he allegedly sent to notorious child sex trafficker Jeffrey Epstein.

Trump had filed a $10 billion lawsuit against the publication, but it was dismissed by a federal judge in April for failing to meet the legal "actual malice" standard required for public figures.

Photographer Andrew Harnik was also awarded for his iconic photo featuring Trump looking lost and confused in the Oval Office after a man collapsed behind him during an event last November.

The image immediately sparked ongoing speculation about the president's health. Handing out the award, CNN's Wolf Blitzer described it as a "truly striking image of contrast, skillfully captured in a chaotic moment."

Trump was seen repeatedly closing his eyes for extended periods of time as scholarships and awards were handed out.

He ended his remarks on a more gracious note, giving the press a compliment of sorts as he donned a Trump 2028 cap and suggested he would run for a third term.

"I just want to say… I have tremendous respect for the people in this room," he told the crowd.

"Sometimes I don't feel you treat me fair, or maybe you do. I don't know… Your profession is amazing and I want to thank you for having me."