Rosie O’Donnell Then & Now: Photos From Her ‘A League Of Their Own’ Days To Today

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Paige Kindlick, Jessica Acosta

March 12, 2025 7:28PM EDT

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Rosie O’Donnell moved to Ireland. See her best photos from her younger years to today.

Rosie O’Donnell is an American actress, comedian, and former talk show host who has made a name for herself on both the big and small screens. She began her career as a stand-up comedian before landing her first movie role in “A League of Their Own” in 1992. From there, she starred in films such as “Sleepless in Seattle” and “Now and Then.”

In 1996, Rosie launched “The Rosie O’Donnell Show,” a daytime talk show that earned her multiple Emmy Awards.

Click through the gallery to see her best photos from then and now!

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Rosie O’Donnell in 1992

Rosie O’Donnell in 1992 — Rosie O’Donnell (left) posed in costume with Madonna (right) on the set of their film “A League Of Their Own,” in 1992.

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Rosie O’Donnell in 1993

Rosie O’Donnell in 1993 — Rosie O’Donnell wore this patterned coat while posing with a rottweiler on the set of her 1993 “Another Stakeout.”

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Rosie O’Donnell in 1993

Rosie O’Donnell in 1993 — Rosie O’Donnell (left) posed with her co-star Meg Ryan, on the set of the film “Sleepless In Seattle” in 1993.

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Rosie O’Donnell in 1994

Rosie O’Donnell in 1994 — Rosie O’Donnell posed with the cast of “The Flintstones” in 1994. Rosie (left) played the role of Betty Rubble, where she posed in a blue dress.

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Rosie O’Donnell in 1995

Rosie O’Donnell in 1995 — Rosie O’Donnell (far right) posed with the cast of the 1995 film “Now and Then.” Pictured from left to right: Gaby Hoffman, Demi Moore, Thora Birch, Melanie Griffith, Ashleigh Aston Moore, Rita Wilson, Rosie, and Christina Ricci.

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Rosie O’Donnell in 1996

Rosie O’Donnell in 1996 — Rosie O’Donnell cuddled up to her co-star, Michelle Trachtenberg, on the set of the 1996 film, “Harriet The Spy.”

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Rosie O’Donnell in 1994

Rosie O’Donnell in 1994 — Rosie O’Donnell posed in leather with her co-star Dan Aykroyd on the set of the 1994 film “Exit To Eden.”

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Rosie O’Donnell in 2001

Rosie O’Donnell in 2001 — Rosie O’Donnell accepted her Emmy for Best Talk Show Host at the 2001 Daytime Emmy Awards at New York’s Radio City Music Hall in 2001.

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Rosie O’Donnell in 1997

Rosie O’Donnell in 1997 — Rosie O’Donnell performed an opening act with an actor from the cast of “Beauty and the Beast” at the 51st Annual Tony Awards at Radio City Music Hall in New York City in 1997.

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Rosie O’Donnell in 2004

Rosie O’Donnell in 2004 — Rosie O’Donnell (right) held hands with her ex-wife Kelli Carpenter (left) & walked out of San Francisco City Hall in San Francisco on Thursday, Feb. 26, 2004, after getting married.

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Rosie O’Donnell in 2005

Rosie O’Donnell in 2005 — Rosie O’Donnell (left) posed with her co-star Andie Macdowell (right) on the set of the film “Riding The Bus With My Sister” in 2005.

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Rosie O’Donnell in 2012

Rosie O’Donnell in 2012 — Rosie O’Donnell (right) & her ex-fiance Michelle Rounds at the National Board of Review Awards Gala in New York City on January 12, 2012.

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Rosie O’Donnell in 2015

Rosie O’Donnell in 2015 — Rosie O’Donnell rocked this red leather jacket with black skinny jeans at the Go Red For Women Collection show during New York Fashion Week on February 12, 2015.

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Rosie O’Donnell in 2017

Rosie O’Donnell in 2017 — Rosie O’Donnell rocked this oversized tan linen coat with a white tunic & white pants at the LA Premiere of “SMILF” on October 9, 2017.

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Rosie O’Donnell in 2022

Rosie O’Donnell in 2022 — Rosie O’Donnell wore this black coat with a V-neck lack top, black trousers, and dark green patent leather Dr. Martens boots at the Cool Comedy Hot Cuisine Benefit in Los Angeles on September 21, 2022.

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2013 Rhode Island Comic Con – Day 1

2013 Rhode Island Comic Con – Day 1 — PROVIDENCE, RI – NOVEMBER 02: Simon Fisher Becker attends the 2013 Rhode Island Comic Con at Rhode Island Convention Center on November 2, 2013 in Providence, Rhode Island. (Photo by Bobby Bank/WireImage)

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