Video Of The Day: That Time Madonna And Sandra Bernhard Talked About Going To Cubbyhole On National TV
Before viral clips were a thing, Madonna and Sandra Bernhard’s late-night banter about Cubbyhole had everyone talking.
Back in 1988, Late Night with David Letterman got a dose of downtown queer energy when Sandra Bernhard and Madonna showed up in matching outfits, casually dropping hints about their nights at the iconic lesbian bar, Cubbyhole. Fun fact: In ’88, the Cubbyhole wasn’t at its current location on W 12th St. Back then, it occupied the space that’s now home to Henrietta Hudson.
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The Letterman segment, which saw Bernhard teasing about Madonna’s skills in the bedroom—implying she outshined then-husband Sean Penn—was equal parts flirtation, camp, and shock factor. At a time when mainstream culture was still skittish about open discussions of queerness, the duo’s playful innuendo felt edgy. Decades later, the moment still stands as a bold, unapologetic display of queer camaraderie, forever etched in pop culture history.
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