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Rosie O’Donnell Then & Now: Photos

Rosie O’Donnell Then & Now: Photos

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 Then & Now: Photos

Moviestore/Shutterstock

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

March 20, 2023, 10:44AM 2 of 16

Rosie O’Donnell Then & Now: Photos

Touchstone/Kobal/Shutterstock

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

March 20, 2023, 10:44AM 3 of 16

Rosie O’Donnell Then & Now: Photos

Moviestore/Shutterstock

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

March 20, 2023, 10:44AM 4 of 16

Rosie O’Donnell Then & Now: Photos

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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.

March 20, 2023, 10:44AM 5 of 16

Rosie O’Donnell Then & Now: Photos

Matthew Rolston/New Line/Kobal/S

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.

March 20, 2023, 10:44AM

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Rosie O’Donnell Then & Now: Photos

Paramount/Kobal/Shutterstock

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

March 20, 2023, 10:44AM 7 of 16

Rosie O’Donnell Then & Now: Photos

Savoy/Kobal/Shutterstock

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

March 20, 2023, 10:44AM 8 of 16

Rosie O’Donnell Then & Now: Photos

Stuart Ramson/AP/Shutterstock

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.

March 20, 2023, 10:44AM 9 of 16

Rosie O’Donnell Then & Now: Photos

Adam Nadel/AP/Shutterstock

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.

March 20, 2023, 10:44AM 10 of 16

Rosie O’Donnell Then & Now: Photos

Marcio Jose Sanchez/AP/Shutterst

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.

March 20, 2023, 10:44AM 11 of 16

Rosie O’Donnell Then & Now: Photos

The Sanitsky Company/Kobal/Shutt

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.

March 20, 2023, 10:44AM 12 of 16

Rosie O’Donnell Then & Now: Photos

Gregory Pace/BEI/Shutterstock

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.

March 20, 2023, 10:44AM 13 of 16

Rosie O’Donnell Then & Now: Photos

Broadimage/Shutterstock

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.

March 20, 2023, 10:44AM 14 of 16

Rosie O’Donnell Then & Now: Photos

Invision/AP/Shutterstock

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.

March 20, 2023, 10:44AM 15 of 16

Rosie O’Donnell Then & Now: Photos

John Salangsang/Shutterstock

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.

March 20, 2023, 10:44AM 16 of 16

Rosie O’Donnell Then & Now: Photos

WireImage

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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