
On June 27 1988, Madonna and Sean Penn attended the Mike Tyson vs. Mike Spinks fight at the Trump Plaza Hotel & Casino in Atlantic City, New Jersey.

On June 27 1988, Madonna and Sean Penn attended the Mike Tyson vs. Mike Spinks fight at the Trump Plaza Hotel & Casino in Atlantic City, New Jersey.

On June 10 1989, Madonna’s Express Yourself single debuted at #40 on the Hot Dance Music/Club Play Chart in the USA.
Express Yourself eventually peaked at #1 for 3 weeks (starting July 8 1989).
On June 9 2016, the always outspoken, always fabulous Shirley Manson told Yahoo! Music:
“When I look at Madonna, I think Madonna should not give a fuck what anybody has to say about her age. She should explore who she is now. It would be infinitely more interesting [than her] being concerned with whether we find her sexy or not. She’s got so much more to offer than that. She should be like, ‘Kiss my ass. I’m Madonna. I may be old, but I will always have my legacy behind me and you motherfuckers won’t!’ I don’t know why she cares so much.”
Shirley recently recalled meeting Madonna at the 1999 Grammy Awards, where her band Garbage’s 1998 album Version 2.0 and Madonna’s Ray Of Light were both nominated for Album Of The Year:
“I remember that day. I walked past Madonna, and she grabbed my arm. I turned around, and she went, ‘I think you’re amazing.’ I nearly fell on top of her in shock.”
On June 8 1991, Madonna’s Holiday debuted at #12 in the UK. It was the third time that Holiday was released in the UK, this time to promote The Holiday Collection.
The first time the song was released in the UK it peaked at 6. The second time it was released it peaked at number 2, only to be kept away from number 1 by her own Into the Groove. The 1991 released peaked at number 5 during the week of June 15.

On June 7 2019, Gay Times published a review of Madonna’s Dark Ballet music video:
Madonna has released her powerful music video for new single Dark Ballet.
The song, which the Queen of Pop first teased during her Met Gala performance in 2018, is the final track to be released ahead of her highly-anticipated 14th studio album Madame X, which is due out on Friday 14 June.
“They are so naive, they think we are not aware of their crimes. We know, but we are just not ready to act. The storm isn’t in the air, it’s inside of us,” she declares on the experimental track, which also samples the Nutcracker in its autotune-laden bridge.
Queer rapper Mykki Blanco stars in the Emmanuel Adjei-directed video as Joan of Arc, who was famously burned at the stake following numerous charges including cross-dressing – a scene which is powerfully recreated in the clip.
“They judged her. They said she was a man, they said she was a lesbian, they said she was a witch, and, in the end, they burned her at the stake, and she feared nothing. I admire that,” Madonna says of Joan, the inspiration for the video.
The video also begins with a quote from Joan, and ends with a quote from Mykki, which reads: “I have walked this earth, black, queer and HIV positive, but no transgression against me has been as powerful as the hope I hold within.”
After months of speculation, Madonna has been confirmed as the headliner of WorldPride 2019 in New York City.
On 30 June, the Queen of Pop will perform at the Hudson River Park Pier 97 in celebration of the 50th anniversary of the Stonewall Uprising, alongside several other legendary acts such as Cyndi Lauper, Ciara and Grace Jones.