Bill Maher Roasts Trump’s Freedom 250 Festival for Failing to ‘Close the Deal With Milli Vanilli’
Bill Maher criticized Donald Trump's Freedom 250 festival for failing to secure major headliners, including Milli Vanilli. During his monologue, Maher humorously noted the disappointment of not being able to finalize deals with several artists. The festival, set to celebrate America's 250th birthday, has faced backlash and lost multiple performers shortly after announcing the lineup.
- ▪Bill Maher mocked the Freedom 250 festival for its lack of confirmed headliners.
- ▪Several artists, including Martina McBride and Morris Day, withdrew from the event after the initial lineup announcement.
- ▪The festival is scheduled to take place on the National Mall in Washington, D.C., starting June 25.
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Home > Creative Content > TV Shows Bill Maher Roasts Trump’s Freedom 250 Festival for Failing to ‘Close the Deal With Milli Vanilli’ “That’s gotta hurt,” the comedian adds Alyssa Ray May 29, 2026 @ 7:55 PM Share on Social Media Share on Facebook Share on X (formerly Twitter) Share on LinkedIn Share on Email Bill Maher (Photo credit: Stefanie Keenan/VF25/WireImage) 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.
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