Madonna performs in Times Square for a Grindr concert for “Confessions II”Starmax/ZUMA
While watching Madonna’s recent Times Square takeover—sponsored by the gay “dating” app Grindr—it struck me. And I couldn’t stop thinking about it.
Something about Madonna’s performance made me immediately think of Nancy Pelosi. (Do with that what you will.) Both women are legendary trailblazers in their own right, foundational to their respective worlds, and yet always in a complicated negotiation with the legacy they’re leaving behind.
From the very start, both women were dismissed by the world around them, eventually defying expectations and a male-driven culture that wished to deem them unworthy. They both found longevity in their worlds due to reinvention, navigating the changing winds of pop culture or political landscapes by having to shape shift in ways their male counterparts never had to.
It’s hard to put my finger on what exactly sparked the comparison—maybe initially, it was the superficial fact of both being women who take up powerful spaces and refuse to let the world tell them they can’t do powerful things. Maybe it’s also that when these women dare to exist in public, we write about it, talk about it, send clips to our group chats about it.
But there was something else too. As Madonna precariously dangled her leg over the edge of a Times Square banister while she promotes Confessions II, the long-awaited follow-up to her 2005 chart-topping Confessions on a Dance Floor, I was hit with a type of exhaustion. It was a feeling I felt when Pelosi was exiting Congress. Madonna and Pelosi, in all their power, once created the winds of culture and politics. Now, it seems, they chase them.
But maybe that’s real legacy. It’s not about newness or the albums or gavels, but the audacity to still be here, unbothered and reveling in knowing you already did it. In a culture terrified of irrelevance, there’s something loudly radical about two women who’ve already proved everything—and know it.

