Bill Maher used part of his Friday night monologue on Real Time to mock President Donald Trump’s planned Freedom 250 concert series, a celebration tied to America’s 250th birthday and scheduled to run on the National Mall in Washington, D.C., from June 25 to July 10, 2026. Maher ridiculed the lineup, which had included names such as Vanilla Ice, Milli Vanilli, Morris Day, and Bret Michaels, joking that it seemed as if Trump were trying to help the unemployed. He compared the event to Trump’s widely criticized 2017 pre-inauguration concert, which also drew attention for its unusual and underwhelming roster.
The concert series has faced a wave of cancellations and departures. Several performers said they were misled about the nature of the event and were unaware of Trump’s involvement when they agreed to participate. Among those who pulled out were Bret Michaels, The Commodores, Young MC, Morris Day and the Time, and the original singers of Milli Vanilli. Country singer Martina McBride also said she would not perform, stating on social media that she had been offered a chance to appear at a nonpartisan event but later learned the presentation had been misleading. Maher seized on the irony, joking that it must be embarrassing when organizers “can’t close the deal with Milli Vanilli,” a reference to the group’s famous lip-syncing scandal.
Despite the withdrawals, some performers remain listed for the series, including Vanilla Ice and Flo Rida. The event is still set to span nearly two weeks in late June and early July 2026.
Maher also mocked a separate Trump-related proposal: a commemorative $250 bill featuring Trump’s face. He called the idea outrageous and joked that Republicans in Congress were excited about it, suggesting they would be eager to carry it in their wallets. The bit added to Maher’s broader criticism of Trump’s branding efforts, which he framed as another example of the former president inserting himself into national symbols and celebrations.
After the monologue, Maher moved on to a softer interview segment with Neil deGrasse Tyson.
