Madonna auctioned off a variety of personal items, raising more than £5.9 million in the process, and managed to rope in her ex-husband Penn to part with some cash for a good cause.
Madonna sported a short black, gold, and silver-patterned long-sleeve dress, while Penn opted for black suit.
"For once, he's not the one being arrested."
But the night quickly became one freakish event after another - first, Madonna telling the audience that she'd marry Penn again if he laid down a whopping $150,000 donation for a pricey piece of jewelry. One lucky (and deep-pocketed) fan even got to hold Madonna's mic as she accompanied herself on a ukulele-powered version of "Holiday".
Ariana Grande also joined the singer onstage to dance with her and the two also briefly engaged in a double twerking session.
On the topic of the monies raised, Madonna said in a release, "Founding Raising Malawi is one of the most meaningful things I have done in my life". He revealed he had pneumonia and malaria at the time.
A chair Madonna has performed on went for $10,000 after Madonna told the crowd that $600 could send a girl in Malawi to secondary school and $2,000 would cover her university expenses. His mother died in childbirth and his siblings were also dead.
Last Friday, she performed at her benefit, singing her hits such as Don't Tell Me and Beautiful Stranger and covering Britney Spears' Toxic, said E!
The charity is now building an intensive care unit and paediatric surgery in the country - which is due to open next year. AP material published by LongIsland.com, is done so with explicit permission. Though Madonna did say she's very single.
Madonna and Sean Penn, round two?
Real Housewives of NY star Bethenny Frankel captured the singer's antics on her Snapchat.