On May 24 1989, Madonna participated in the Don’t Bungle The Jungle benefit concert to raise money and awareness for preserving the world’s rainforests. The event took place at the Brooklyn Academy of Music, Brooklyn, NY. Madonna performed a rendition of Sonny & Cher’s I Got You Babe with comedian and friend Sandra Bernhard.
On May 21 2001, the U.S. leg of Madonna’s Drowned World Tour continued to sell out performances in the final seven markets that went on sale the previous weekend. A press release stated that the tour, promoted by SFX, promised to be the most extravagant stage spectacle of Madonna’s career thus far. The last batch of cities announced for the tour included sold-out dates in New York, New Jersey, Washington, Miami, Atlanta, Las Vegas and Los Angeles. It was also announced that due to overwhelming demand, an additional three shows in New York and two in Los Angeles had been added to the itinerary, with tickets to go on sale May 30th.
On May 20 2015, Madonna acknowledged David Letterman’s retirement on Twitter:
@letterman Awww Dave I’m gonna miss you! Where am i gonna go on T.V. When I wanna say the F word? do you still have my panties???? this ❤#rebelheart loves you! – Madonna
On May 19 1995, the music video for Human Nature premiered on MTV.
Madonna had initially planned to have friend and collaborator Alek Keshishian direct the video for Human Nature. Keshishian had even been named as the director in ICON Magazine, but for unknown reasons this shoot was cancelled during pre-production. Madonna later called in another recurring collaborator – Jean-Baptiste Mondino – to direct the clip instead.
The video marked Madonna’s first collaboration with Jamie King, who can be spotted as a dancer in the video.
On May 18 1994, Madonna made a surprise appearance on NBC-TV’s The Tonight Show, hosted by Jay Leno.
Watch this classic Madonna interview here: