Sandra Bernhard Reflects on 'Sad' End of Friendship with Madonna

The Roseanne and Pose actress opened up about her life in New York in the 1980s and '90s, her comedy career, her time working with Jerry Lewis on The King of Comedy, her 30 appearances on Late Night with David Letterman and, of course, her former friend Madonna on Jesse Tyler Ferguson's podcast, Dinner's on Me.

"Everybody talks about your friendship with Madonna," Ferguson said. "I do remember something that you said that really stuck out to me was that you're such a such a loyal and sensitive person, maybe the separation of that friendship was a little bit harder on you than it was on her yet if you saw each other tomorrow, it'd be fine."

Bernhard confirmed that "it would be fine."

"I hate getting nostalgic and caught up on that time because it was such, like, the perfect time," Bernhard continued. "The late '80s when I was doing my one-woman show here in New York, and I was friends with her and doing Letterman all the time, I mean everything was just so fresh."

The two, who quickly became friends in the New York club scene, were a powerhouse in the late '80s and early '90s, even making a joint 1988 appearance on Letterman in matching outfits while joking about going to the lesbian bar, the Cubbyhole, together.

"There are times when I'm like, 'That really makes me sad, you know, that we couldn't maintain our friendship,'" Bernard added. "I mean, I could have [maintained our friendship]."

Bernhard revealed that by 1992 they were no longer on speaking terms and previously said that the singer's "relationships just don't last."

In 2021, the comedian appeared on the Hot Takes & Deep Dives podcast and dished more about their "iconic" relationship, albeit short lived.

"Our whole friendship was [iconic]. There are only a handful of photos of us and we went out quite a bit. We were out and about and it's amazing how few pictures there really are of us," she mused, before being asked what she took away from their time as friends.

"For me, I learned that I didn't really like that level of visibility and having to work it constantly. We all as performers work it to a certain degree, but I'm a very improvisational person, on stage and in my life, and I don't like being tied down in having to be a certain way for my image," she replied. "Therefore, I feel I continue to evolve as a person and personality."

"What I tried to impart in our friendship is, 'I'm really your friend, I’m not just somebody that’s passing through,'" she added, before teasing why their friendship fell apart.

"And I guess for a while we had a real friendship, but it's hard for somebody like her. She doesn't really want somebody around who reflects too much of who she is," she added. "Therefore, her relationships just don't last."