Jul 23, 2026 · 29 min · 12 segments
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Katie HayesHostKatie, it feels like Madonna, one of the biggest pop stars of the 80s, 90s, really just all of pop music, is back in the headlines once again.
She's got the celebration tour, she's got documentary projects, she's made comments reflecting on past marriages, relationships, all this stuff is coming up again.
Madonna just somehow finds a way to remind everyone that she's lived about five or six lifetimes in one.
And whenever people talk about Madonna's relationships, there's really one name that always comes up, and that's Sean Penn.
They were both young, they were very, very famous, they were beautiful, and they were volatile.
This four year marriage became one of the defining celebrity romances of the 80s.
We're going to get into all of it and find out how one of Hollywood's most explosive marriages became one of the strangest second acts.
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