rambling rosie

Rosie O’Donnell dishes on partying with Madonna in the ‘90s & where their friendship stands today

By · Updated on January 26, 2024
A paparazzi photo of Rosie O'Donnell and Madonna standing next to each other at an event, both wearing black.
Image Credit: Getty Images

When TikTok blew up in popularity at the beginning of the pandemic, we never would’ve expected that iconic actress and comedian Rosie O’Donnell would become one of the platform’s most prolific posters.

And yet, three years later, here we are. Most days, you can find her spilling tea and having a laugh in one her now-famous “ramble” videos.

Frankly, we’re just happy to have her back in our lives on a regular basis. You could even say she’s experiencing something of a “Rosie-ssance,” between the frequent TikToks, and her roles from the past year in American Gigolo, The L Word: Generation Q, and the TV update of A League Of Their Own.

Related:

Rosie O’Donnell shares her son’s hilarious reaction to seeing ‘A League Of Their Own,’ 30 years later

“It was the weirdest thing I’ve ever seen!”

Speaking of League, that beloved ’92 sports dramedy gifted us with one of our favorite showbiz friendships—O’Donnell and Madonna—and the comedian recently opened up about their connection in a series of TikToks.

After Oscar night last week, O’Donnell admitted she doesn’t enjoy going to the award show—or its after-parties—because it is “very stressful” and she’s “a little bit of an introvert.” The post prompted a follower to comment and ask, “How many of Madonna’s after parties have you attended over the years?”

A few days later, O’Donnell responded to the comment in a separate video, saying she did, indeed, go to a few soirées at Madonna’s but, from the sound of it, often “left early” before they got too debaucherous, or brought a family member along.

When a fan asked if said parties were “wild or mostly tame,” it inspired yet another Rosie Ramble™ in which she said Madonna’s bashes were “great” but not especially “crazy.” Instead, O’Donnell mostly went off on a tangent about the pop star’s beautiful Miami home off of Biscayne Bay:

“I had my own house in Miami for many years, really because of Madonna,” O’Donnell shares. “I never was a person who vacationed in Florida until after A League Of Their Own and I stayed with her, and I thought, ‘This is how the rich people live.'”

Related:

Rosie O’Donnell dishes on partying with Madonna in the ‘90s & where their friendship stands today

O’Donnell has got Madonna stories for days!

So, yeah, O’Donnell’s not necessarily dropping any hot gossip in these TikToks—unless you’re looking for tea about coastal Florida real estate in the ’90s—but we can’t help but grin hearing her reminisce about the good ‘ole days with Madonna.

In the comments, one curious follower asked, “What happened to your relationship with Madonna?” O’Donnell wrote back: “Nothing—still going strong.”

Another shared their appreciation for the star’s stories about Madonna, remarking that, “the hate against her is overwhelming at times,” which prompted O’Donnell to respond, “Yes, but she’s a rebel an artist an outlaw and she always delivers—[once-in-]a generation star.”

And we have to agree—we love “Madonna Story Time” with Rosie! Here’s hoping O’Donnell keeps up the rambles. And, hey, we know Madonna loves to chat with TikTok stars; maybe one day soon she’ll reunite with her old pal for a live reunion. A girl can dream!

Watch Rosie’s TikTok spilling the deets on her past with Madonna below:

@rosie

Replying to @cle9764

? original sound – Rosie ODonnell

Related:

Madonna just went on TikTok’s favorite live-show and huffed a bottle of poppers

Honestly? Queen.

Don't forget to share:

Help make sure LGBTQ+ stories are being told...

We can't rely on mainstream media to tell our stories. That's why we don't lock Queerty articles behind a paywall. Will you support our mission with a contribution today?

Once Monthly Annually

Cancel anytime · Proudly LGBTQ+ owned and operated