Bill Maher mocked Donald Trump’s Freedom 250 festival after organizers failed to secure a number of headliners, including Milli Vanilli.
“We’re having a big 250th birthday party for America. A concert. They announced the lineup,” Maher explained during Friday’s monologue for “Real Time.” “Oh, Vanilla Ice, Milli Vanilli, Morris Day, Bret Michaels. I think it’s very admirable about the president, it shows he’s concerned for the unemployed.”
However, as Maher quickly pointed out, after they announced “this all-star lineup, a lot of them said, ‘No. What are you talking about? We’re not playing.’”
At this update, Maher quipped: “That’s gotta hurt a lot, when you can’t close the deal with Milli Vanilli.”
The Great American State Fair, which is organized by President Trump’s nonprofit Freedom 250, is a 16-day patriotic celebration on the National Mall in Washington, D.C. It is set to kick off on June 25.
Organizers announced the lineup for the patriotic event, which initially included Martina McBride, Morris Day and The Time, The Commodores, Bret Michaels, Vanilla Ice, Flo Rida and C+C Music Factory, among others.
At the time of the lineup reveal, organizers promised the festival would “bring together all 56 U.S. states and territories in a World Fair-style celebration of America’s 250th birthday, featuring live entertainment, immersive exhibits, patriotic tributes, innovation showcases, cultural programming and family-friendly attractions stretching from the U.S. Capitol to the Washington Monument.”
The Treasury has plans for a $250 bill with Trump’s face on it. You can use it to buy gas. pic.twitter.com/t5cAeXRjw2
— Bill Maher (@billmaher) May 30, 2026
“The Great American State Fair will feature mainstage performances by legendary artists every Thursday, Friday and Saturday night,” the statement continued. “In the upcoming weeks, Freedom 250 will continue to announce more incredible performers, speakers and participants.”
However, in the days following, several of the acts bowed out, including McBride, Day, The Commodores, Young MC and Michaels. Additionally, the event was criticized by Jimmy Kimmel, Jake Tapper and Megyn Kelly, with the latter calling it “a disaster from start to finish.”
C+C Music Factory, Vanilla Ice and Flo Rida are still listed on the Freedom 250 lineup, with additional names expected to be announced.
New episodes of “Real Time With Bill Maher” air on Fridays on HBO.
