Rosie O'Donnell: In A League of Her Own

June 24, 2025·55 min·5 clips

On The View in December 2006, Rosie O'Donnell said Donald Trump 'got bankrupt so many times' and was 'not a self-made man' — and Trump immediately threatened to sue and launched a public attack campaign.

The warning lands first. Before the biography gets moving, the hosts flag sexual abuse in the story, then slide into a workplace bit about being outspoken. Rosie fits the lane. She comes across as someone whose career keeps turning on strong opinions and a refusal to sand herself down. The timeline starts in the eighties. At 22, Rosie is a Long Island stand-up with a thick accent, an easy-to-recognize act, and enough drive to get into bigger rooms. Then Hollywood calls. The clip settles on A League of Their Own, where Rosie plays Doris Murphy, a wise-cracking third baseman with more under the hood than the jokes first suggest. Madonna becomes her screen partner, which gives the hosts plenty to enjoy: Rosie from Long Island suddenly buddy-buddy with the most famous woman in the world. The cast is loaded. Tom Hanks and Geena Davis are there too, but the excerpt says Rosie and Madonna steal pretty much every scene they're in. Doris also gets a real emotional beat. In the movie moment, she talks about being made to feel wrong, strange, or unlike other girls because she could play. That scene kicks up the argument. Some people hear Doris as someone who might bat for the other team, while Penny and Rosie disagree about what the exchange is doing. Penny asks for a different read. Rosie thinks Doris is in love with Mae, so she does the scene again without really changing the center of it. The hosts clearly enjoy the nerve. Rosie hears the truth in the writing, gives the note a polite nod, and keeps playing it her way. Then the box office backs her up. By September, the movie passes the $100 million mark and becomes the highest-grossing baseball movie of all time.

As heard by us

A brisk Rosie O'Donnell profile that moves from stand-up to stardom and back into showbiz drama.

The episode follows Rosie O'Donnell from 80s stand-up and a thick Long Island accent into movie stardom and a turn as a talk show host, then stays with the mess that follows when she steps away from showbiz and comes back to it.

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Why you'd press play

Press play for Rosie O'Donnell's rise from 80s stand-up to movie star and talk-show force.

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