Madonna's always been a bit of rebel heart, and she certainly wasn't going to tame her behaviour for her son's charity gala.
Inspired by her little boy, David Banda, who she adopted from Malawi, the 58-year-old hosted Madonna Presents An Evening of Music, Art, Mischief and Performance to Benefit Raising Malawi.
Taking place on Friday, in Miami, the night was filled with celebrities, romance, political agenda and whole lotta cash.
The starlet auctioned off rare photographs, tour memorabilia, and pieces from her own art collection
And with the help of her star-studded guest list including Sean Penn, Leonardo DiCaprio, Chris Rock, Bethenny Frankel James Corden, Courtney Love, Adriana Lima and Paris Hilton, she raised over $7.5 million for the African nation.
Raising eyebrows, along with all the money, Madge decided that she should turn the auction onto herself... and ex Sean Penn.
The singer, who was Mrs Penn for four years between 1985 to 1989, told the crowd she'd remarry the actor if he bid $150,000.
Real Housewives star Bethenny Frankel recorded the whole thing on Snapchat.
“I’m still in love with you,” Madonna gushed.
Indulging his former wife, Sean handcuffed Madonna and crawled through her legs at one point.
"For once, he's not the one being arrested," she joked.
There was certainly a lot of attention on the former flames, with Madonna putting up for auction three black and white photos from her 1985 wedding to Sean, shot by the late photographer Herb Ritts.
The stunning images were said to be sold for $230,000.
Other items being auctioned included a weeklong stay at Leonardo DiCaprio’s Palm Springs’ home, which went for $140,000 and a custom-designed Fiat 500 inspired by the lady of the hour.
While it was an “evening of music, art, and mischief”, the reason behind it was a lot more sobering.
Madonna was inspired to raise much needed funds and awareness after adopting her son from Malawi.
A documentary about his life revealed his birth mum had died in childbirth. David, who was suffering from pneumonia and malaria at the time, had also lost his three siblings were also dead when Madonna adopted him.
The brave 11-year-old took to the stage to share a bit about himself, “My name is David. Now you know a little bit about Malawi and how I met my mother.”
“I realize I’m one of the lucky ones,” he added, before introducing his mother.
Of course Madonna shared her creative flair, dipping into her clown alter-ego for a slowed down performance of toxic.
The singer also danced with Chris Rock, before being joined by Ariana Grande in what can only be described as "gyrating" performance.
Check it out in the video below!