Madonna Confesses & Undresses in Free Times Square Concert
The Grindr-sponsored promo gig included six songs, a tribute to queer trailblazers and one leg dangled perilously over a plexiglass barricade
June 5, 2026
Madonna’s semi-surprise pop-up concert in Times Square Thursday was a joy-filled ode to club music, a re-upping of her loyalty to queer people and a community family reunion — with the Queen of Pop as our saucy mistress of ceremonies.
I’d heard from a Facebook friend that she was doing a gig in Times Square, but I couldn’t get it confirmed until the day it was happening. By then, people were noticing the increasingly popular TSX stage in Times Square was coming alive, a spot utilized in the past by Charli XCX, Post Malone and Shakira, so the cat was pretty much out of the bag.
Still, while Grindr kept reminding users to stay tuned for a big Madonna drop, it wasn’t until much closer in that it became clear that the big surprise was a streaming live performance.
This information is the hottest thing I’ve ever picked up on Grindr.
I wound up scoring a wristband and headed over by 3 p.m. There was still no official confirmation (because it’s outdoors in a crowded area, the City of New York does not want these things to become madhouses), so only about 75 or so fans were milling around, including some of the “famous” ones. Seeing them is always a comfort that you’re on the right track and she isn’t going to throw a curveball and show up somewhere else.
I stood with my pals in what was basically a perfect spot, oblivious to where any VIP area might be. I couldn’t see how much of an improvement a different spot would make — really, anywhere facing that elevated stage is just great.
There was a pink Grindr bus with a disco ball and dancing sluts behind us!
Just before the 20-minute gig kicked off, I realized VIPs were invited to stand on the tall stairs directly across from the stage. Being more level with Madonna was enough of an improvement that I took off and got in that line, winding up near a couple of really sweet guys I’ve known forever, but haven’t seen in a couple of album cycles. Confessions on a Dance Floor Part II (out July 3) really brings the people together.
Guy Oseary and Mercy James were also up there.
You’ve all probably seen the show by now via YouTube, but I have to say it was absolutely perfection. Madonna looked stunning (those eyebrows are back) in a silver jacket and boots and a pink corset, and Euro-chic in blue shades.
She emerged singing “I Feel So Free,” one of her most infectious numbers in forever.
One of my favorite parts of the whole thing was when she did her little gay trip-walk across the stage. “C’mon gays! Guys! And dolls!” she teased, stripping the jacket away to reveal that her color scheme rendered her a human trans flag.
While this was happening, her dance troupe — who’d been dancing on the street — ran up to join her. While they were en route, she turned her Sabrina Carpenter duet “Bring Your Love” into a solo, spreading her legs around a prop speaker, a reference to a promo image for Confessions 2.
“Are you ready? It’s mutha,” she said. We were and she was.
Next up, it was time for “Love Sensation,” her newly released sample of the album — and it’s fucking amazing. (I briefly died when she fucked around with Stuart’s set-up, inducing a minor panic.)
This is like this album’s “Get Together” … and wouldn’t you know, she performed “Get Together” for the first time properly in 20 years. Deep cuts!
“There’s nothing that we can’t do” the song goes, and nothing Madonna won’t do to satisfy her fans his era. Loved seeing her sitting and rocking back and forth cheerfully to this one, and it was especially powerful when she went quiet and honored queer trailblazers with projections of Stonewall rioters, Marsha P. Johnson, Keith Haring, Robert Mapplethorpe and more.
Madonna proudly declared she would perform a song “I wrote for this city!” — her anthemic “I Love New York,” a cheeky rock anthem that hits different considering how many people voted for Spencer Pratt in L.A. (Not enough, Spencer — ha-ha!)
After two big surprises, she gave us one of her best songs of all time, “Hung Up,” making the show half old and half new.
My God, when she tours this time — and she will — it’s gonna be all Confessions all the time, isn’t it? Both the 2005 and 2026 versions.
“Thank you, New York City! I love you! Happy Pride!” she said, vanishing as flyers thanking us for coming rained down.
This show proved Madonna is still able to command a stage nearly 50 years after she arrived in Times Square with 35 bucks in her pocket. She is also becoming increasingly comfortable with the nostalgic element of her work, weaving classics into new creations forged in her classic sound.
The nostalgic element reminded me that in another major Times Square appearance back in 1987, Madonna had pointed out she’d been in the city for 10 summers, going from street urchin to creamy-smooth-pop-icon-goddess. It’s insane to think she was only 10 years in NYC in 1987, and that that moment happened 39 years ago.
But through it all, we’ve had Madonna — the good one, the naughty one, the generous one, the bitch, the diva, the mutha.
I look forward to never knowing a time without her. She can live to 110 and I’ll live to 100.
Enjoy the photos I took! I’m an archivist at heart, so whenever I get great access, I like to share. Please subscribe! I promise you’ll like some of the stuff I post.⚡️
The next best thing to being there is you being there to document it.
Thank you for reporting from the front lines x