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Music World > News > Madonna Transforms Times Square Into Pride Month Party With Surprise Grindr Pop-Up Show
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Madonna Transforms Times Square Into Pride Month Party With Surprise Grindr Pop-Up Show

Written by: News Room Last updated: June 5, 2026
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After teaming up with Grindr to take over the gayborhood grid in April, Madonna and the LGBTQ+ app joined forces on Thursday (June 4) to transform Times Square with a surprise Pride Month pop-up performance at a new venue, The Square.

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The venue is unusual in the sense that you don’t realize it’s a concert space until suddenly it is. One moment you’re looking at an LED screen in Times Square, the next moment its previously invisible walls are diving inward to reveal a performance space; it’s as if one of the Times Square skyscrapers suddenly opened up to reveal the coolest secret party going on behind the walls of the world’s most photographed intersection. And you don’t have to squint: 18,000 square feet of LED screens are there to help boost what’s going on inside the in-building space (at least until the walls close back up).

At 6:27 p.m. ET, the more-or-less invisible doors of a Times Square LED screen opened to reveal the Queen of Pop’s surprise performance, which opened with the undeniable Confessions II jam “I Feel So Free” backed by Stuart Price on the turntables. (Price is the visionary producer behind her 2005 classic Confessions on a Dance Floor, who has returned to the studio for Confessions II.) After touching forefingers like God and Adam, Madonna and Price invited New York into their confessional jam session, which encompassed three tracks from Confessions II and three tracks from Confessions on a Dance Floor.

“All right New York City, are you ready for this?” asked Madonna, a human who showed up to New York City in the late ’70s with $35, a dream and a lot of moxie and then conquered the world. “C’mon, gays. Happy Pride!” The Grindr-sponsored event opened with “I Feel So Free,” “Bring Your Love” (minus duet partner Sabrina Carpenter) and new track “Love Sensation.” Even in the live setting amid one of the world’s busiest intersections, “Love Sensation” felt like an astoundingly strong tease of Confession II — not a pop single, but a future fan favorite.

After teasing Confessions II with a coterie of choreographed dancers, Madonna offered up a pinch-me medley of tracks from Confessions on a Dance Floor, starting with the low-key fave “Get Together,” moving into the saucy “I Love New York” and concluding with “Hung Up” (and briefly straddling the plastic barrier separating her from the crowd with her leg, naturally). Between the Confessions to Confessions II switchover, Madonna flipped the in-venue lights to the Pride flag and turned Times Square into a massive screening room for a montage of Pride’s radical, riotous roots.

Of the audience, a select lucky group of fans caught the best vantage point of the 15-minute show from the TKTS red steps in Times Square, courtesy of Grindr; meanwhile, despite the on-street barriers, a slow but steady stream of tourists filtered through the Times Square hub, many of them jamming out to era-defining hits like “Hung Up” while walking down the sidewalk, seemingly oblivious to the fact that the artist herself was performing the music above them.

The Madonna x Grindr collab launched in late April with an exclusive picture disc of Confessions II, the hotly anticipated sequel to Madonna’s 2005 masterpiece Confessions on a Dance Floor. The collab continues with a limited-edition Madonna x Grindr merch capsule collection including hats and t-shirts sporting lyrics and imagery from the picture disc artwork (some of the merch was available at a nearby Times Square after party).

Recently, Madonna sat down with Ivy Mugler, Raul Lopez, Jeremy O. Harris, Bob the Drag Queen and Marcelo Gutierrez for a genuinely confessional Grindr chat, where she revealed the best sex of her life and talked about the best bedroom playlist.

What The Sphere has been to Las Vegas, The Square hopes to be for New York City, reimagining concerts as cultural multimedia experiences. One bonus: the space operates within a hotel, so artists can potentially move from their hotel room to a worldwide stage without ever exiting the building. While Madonna isn’t the first to occupy this space (Charli xcx and others have performed there recently in more limited capacities), she’s the first to play The Square at its full operational strength. As always, many artists will likely follow in Madonna’s footsteps, taking this one-of-a-kind Times Square stage before the year is over.

“We thought she was the right person to talk across multiple generations of fans,” says Jeff Marks, the CEO of Innovative Partnerships Group, the company behind turning the Times Square space into The Square. “Young fans still like her, as we saw when she popped up at Coachella with Sabrina. She’s at the World Cup [headlining its first halftime show alongside BTS and Shakira on July 19]. You don’t get someone better than her, who can talk to anyone in the world. I don’t think anyone would say they don’t like her. And, with the brand that was chosen, I think it’s going to give them their big Hollywood moment, and they’ve been around for a while.”

Twenty-four hours after turning Times Square into a dancefloor, Madonna will appear at Tribeca Festival on Friday (June 5) night, screening a 10-minute visual project centered around the first six tracks from Confessions II. After the premiere, Madonna and the project’s directors — David Toro and Solomon Chase (TORSO) – sit down with Jimmy Fallon for a conversation.

In late April, Madonna popped up with Sabrina Carpenter during Sab’s second weekend at Coachella; their duet “Bring Your Love” dropped shortly thereafter and hit the Billboard Hot 100, peaking at No. 74. Album preview “I Feel So Free” went No. 1 on Billboard’s Dance/Mix Show Airplay chart, becoming her first No. 1 on that tally in 18 years. Confessions II, which reunites her with OG Confessions producer Stuart Price, drops July 3.

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