On “Real Time,” Bill Maher mocked Donald Trump’s Freedom 250 festival after organizers struggled to land major headliners, including Milli Vanilli, and multiple acts later backed out.
Bill Maher kicked off Friday’s “Real Time” monologue by zeroing in on the one thing Donald Trump’s Freedom 250 festival couldn’t seem to secure: the headliners.
Maher mocked the pitch that the event would serve as a “big 250th birthday party for America. ” complete with a concert and an announced lineup. “They announced the lineup. ” Maher said. rattling off names including “Vanilla Ice. Milli Vanilli. Morris Day. Bret Michaels.” Then he added a joke that landed on the same tension everyone has been watching unfold around the festival: “I think it’s very admirable about the president. it shows he’s concerned for the unemployed.”.
But the punchline came as the story shifted from who was booked to who wouldn’t show. Maher pointed out that after “this all-star lineup” was unveiled, “a lot of them said, ‘No. What are you talking about? We’re not playing.’”
At that update, Maher couldn’t resist. “That’s gotta hurt a lot, when you can’t close the deal with Milli Vanilli.”
Freedom 250’s Great American State Fair—organized by President Trump’s nonprofit Freedom 250—has been billed as a 16-day patriotic celebration on the National Mall in Washington. D.C. set to kick off on June 25. Organizers initially announced a lineup that included Martina McBride. Morris Day and The Time. The Commodores. Bret Michaels. Vanilla Ice. Flo Rida and C+C Music Factory. among others.
In the lineup reveal, organizers promised a World Fair-style celebration tying the festival to the country’s 250th birthday. Their statement said it would “bring together all 56 U.S. states and territories” with “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 same statement added that the Great American State Fair would feature “mainstage performances by legendary artists every Thursday, Friday and Saturday night,” and that “in the upcoming weeks” Freedom 250 would continue to announce “more incredible performers, speakers and participants.”
The problem, as Maher framed it, was what happened after those early announcements. In the days that followed, several of the acts bowed out, including McBride, Day, The Commodores, Young MC and Michaels. Still listed on the Freedom 250 lineup are C+C Music Factory. Vanilla Ice and Flo Rida. with additional names expected to be announced.
The festival’s setbacks didn’t stop at the entertainment roster. The event was criticized by Jimmy Kimmel, Jake Tapper and Megyn Kelly, with Kelly calling it “a disaster from start to finish.”
A separate thread has also fed the conversation around Freedom 250 beyond the stage. Maher posted about the Treasury’s plan for a $250 bill with Trump’s face on it, writing: “The Treasury has plans for a $250 bill with Trump’s face on it. You can use it to buy gas.”
Even with the lineup reshuffling, the show must go on—at least on paper—for Freedom 250’s Great American State Fair as it prepares for June 25 on the National Mall. And on “Real Time,” Maher made sure the missing headliners weren’t forgotten.
Bill Maher Real Time Freedom 250 Donald Trump Great American State Fair Milli Vanilli Vanilla Ice Morris Day and The Time The Commodores Bret Michaels Flo Rida C+C Music Factory Martina McBride Young MC Jimmy Kimmel Jake Tapper Megyn Kelly