Once upon a time, in 1988, noted comic Sandra Bernhard appeared on Late Night With David Letterman and brought along a special friend who happened to be wearing a matching outfit to surprise him. That friend was her rumored lover, Madonna, who spent the late ’80s carousing with Sandra, hitting up ancient NYC lesbian bar Cubbyhole, and dating Sean Penn. (If these things seem incongruous, then you’ve obviously never seen The L Word.)
At the time, Madonna was starring in David Mamet’s Speed the Plow on Broadway, which any young aspiring actress would consider the accomplishment of her lifetime. Madonna, however, basically shit-talked the whole project on Letterman in the middle of the run. Because she’s #sopunk.
There’s also a point in which David Letterman asks if he can hang out with Sandra and Madonna when they go clubbing, to which Madge snorts, “Maybe if you get a sex change…” Cue teenage girl fits of giggling.
And finally, they “staged” what the annals of Wikipedia would call “a sexy confrontation” in which Madonna accused Sandy of using her to get to Sean Penn, to which Bernhard replies, “You were much better [in bed].”
Educate yourselves on queer celebrity flings of future past by checking out a very special #TBT below.
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