Bill Maher mocked Donald Trump's troubled Freedom 250 concert plans on Friday night, joking that the president 'can't close the deal with Milli Vanilli' after a string of performers abandoned the celebration.

The HBO host took aim at the event during his monologue on Real Time with Bill Maher, ridiculing a lineup that has been depleted by a growing list of cancellations.

'After they announced this all-star lineup of musical guests, a lot of them said, "No, what are you talking about? We're not playing,"' Maher said. 'That's got to hurt a lot - when you can't close the deal with Milli Vanilli.'

The jab referenced one of pop music's most infamous scandals.

Milli Vanilli won the Grammy Award for Best New Artist in 1990 before it emerged that the duo had lip-synced songs recorded by studio musicians. The Recording Academy later revoked the award, marking the first - and still only - time a Grammy has been rescinded.

One half of the original duo, Fab Morvan, is still scheduled to perform at the Freedom 250 concert alongside Vanilla Ice.

Maher continued: 'Inviting Milli Vanilli and Vanilla Ice is very admirable about the president. It shows he's concerned about the unemployed.'

He then broadened his criticism of Trump, turning his attention to a proposal by Republican Congressman Joe Wilson to create a $250 bill featuring the president's portrait.

'Here's something in the category of wow, we never used to be this country,' Maher said. 'They're putting out a $250 bill with Trump's face on it.'

He added: 'Republicans in Congress are thrilled about it. They can't wait to carry it in their wallet. What a switcheroo: having Trump's face next to their ass.'  

The jokes came as Trump's Freedom 250 concert faces mounting scrutiny after at least five headline acts pulled out of the event, which is scheduled to take place on the National Mall in Washington, DC, from June 25 to July 10.

Poison frontman Bret Michaels, country singer Martina McBride, R&B group The Commodores, rapper Young MC, and Morris Day all withdrew after the lineup was announced.

Several performers said they had been led to believe the concert would be a nonpartisan celebration before learning of its ties to Trump and his administration.

McBride said she had been assured the event was intended to celebrate all 50 states and bring Americans together.

'I was presented with an opportunity to perform at a nonpartisan event but that turned out to be misleading,' she wrote on X.

Young MC similarly said he had no idea the concert was considered a Trump-backed event and later described the booking process as a 'bait-and-switch.'

Freedom 250 was launched to help organize celebrations marking America's 250th anniversary in 2026 and works alongside the White House Task Force 250 and the federally backed America250 Commission.

The concert has been overshadowed by a string of high-profile cancellations since the lineup was announced.

Despite the departures, Vanilla Ice has remained one of the event's most vocal supporters.

Speaking to TMZ this week, the rapper said he viewed the concert as a celebration of America rather than a political event.

'I'm here to party with America, man. Music is made to bring people together and that's what we are here to do,' he said.

The Ice Ice Baby star added: 'I don't even vote, so I don't even care. If Biden called up and said, "My daughter is getting married, we need Vanilla Ice," I'd go play.'

He later urged critics not to take the concert so seriously, saying: 'Come on, enjoy the dancing. Don't take it so serious. We're just entertainers, man.'

The remaining lineup includes Vanilla Ice, Flo Rida, C+C Music Factory and Morvan.

The Daily Mail has reached out to the White House for comment.