Madonna has raised more than $7.5m (£5.9m) for the African nation of Malawi by auctioning treasures collected throughout her career.
Dressed in a pink sequined clown top and fishnet stockings, the singer also performed at the star-studded fundraiser in Miami on Friday night and admitted she was "ashamed" to be an American.
Among the crowd was James Corden as well as Leonardo DiCaprio, comedian Chris Rock and Madonna's ex-boyfriend A-Rod.
The pop star auctioned off a number of items from her career including pieces from her art collection, a costume from her tour modelled by singer Ariana Grande and black and white photos from Madonna's 1985 wedding to ex-husband Sean Penn.
The photos, taken by the late Herb Ritts, sold for $230,000 (£180,000).
Sean, who attended the fundraiser and bid on several pricey items when the auction stalled, handcuffed Madonna and crawled through her legs at one point as the two tried to coerce the audience to bid higher.
"For once, he's not the one being arrested," she joked.
She coyly said she'd been in Donald Trump's bed, but later revealed it was for a magazine photo shoot and that Trump wasn't there -- and she criticised his cheap sheets.
"They won't be Egyptian cotton because we all know how he feels about Muslims, don't we," she said as some audience members gasped.
During her performance she gyrated to a slowed-down version of Britney Spears' Toxic and seductively sang "You know that you're toxic", as images of Trump appeared on a large screen behind her.
Other notable items sold during the auction included a painting by British artist Damien Hirst and a print by Trace Emin, which sold for $550,000 (£430,000).
A week-long stay at Leo's home in Palm Springs fetched $140,000 (£109,000).
Madonna adopted her 11-year-old son David from an orphanage in Malawi more than a decade ago. At the time, she said "I didn't know where Malawi was" on the map. David had pneumonia and malaria. His mother died in childbirth and his siblings were also dead.
He was on hand to introduce his mother, telling audience members who paid at least $5,000 (£3,900) per plate: "I realise I'm one of the lucky ones."
The pop star showed videos of Malawi, asking for help to build a paediatric surgery and intensive care unit at a hospital there.
Fifty percent of the population there is under the age of 15, according to her foundation Raising Malawi.
She also spoke out about the plight of Native Americans and asked why their land was being destroyed.
"It just really makes me feel ashamed, ashamed to be an American, ashamed to be a human being really," she said before launching into American Life.