The Stunning Transformation Of Rosie O'Donnell

At one point in the '90s, Rosie O'Donnell was everywhere. She was starring in movies like "A League of Their Own" and "Harriet the Spy" while also hosting her very own daytime talk show (via IMDb). Nowadays, O'Donnell has been keeping a bit of a low profile, but can still be seen in shows like "SMILF," "I Know This Much Is True," and "The L Word: Generation Q." With a decades-long career, you've seen O'Donnell go through a bit of transformation leading to where she is today, and it's all thanks to an invitation she received in 1984 to appear on "Star Search." 

According to Showbiz Cheatsheet, the comedian got her big break in Hollywood after competing in the talent competition show doing stand-up. She told Larry King in 2002 that winning "Star Search" was a big deal, because it gave her "national exposure" (via CNN). From there, she was able to really make her mark in Hollywood as an actor. 

In the early '90s, O'Donnell was the comedic relief in films and avoided typecasting

O'Donnell's first acting role was in the TV show "Gimme a Break!" where she played Maggie O'Brien. It wouldn't be until 1992 that she would make her feature film debut in "A League of Their Own," starring Tom Hanks and Geena Davis. O'Donnell stood out not just because she had the baseball skills – "I played with my brothers and in little league," she told Entertainment Weekly in 1992 (via E! Online) — but she also had the comedic timing. The comedian would even keep the extras entertained during downtime by singing Madonna songs, which Megan Cavanagh (Marla Hooch) said was "so fun to watch." 

From "A League of Their Own," O'Donnell would be cast in another Tom Hanks film — "Sleepless in Seattle." But this time, it wasn't her baseball skills or comedic timing, but her friendship with Madonna that would help her get cast. O'Donnell told USA Today that she credits Nora Ephron's son Jacob for getting her the part, because he wanted to "meet Madonna." The actress also said the film opened doors for her professionally, because after being cast as a "tough tomboy," she got to play Becky who "was a high-class hetero." O'Donnell said, it "helped [her] career not be so narrow," and ultimately allowed her to play characters like Betty Rubble in "The Flintstones."

By the late '90s, cracks in the 'Queen of Nice' crown started to appear

With her success in Hollywood, O'Donnell transitioned into a talk show host with "The Rosie O'Donnell Show" in 1996. This is when she would get the reputation of "Queen of Nice," according to CBC. However, as Vulture reported in 2013, this "nice" reputation was a bit unfair to O'Donnell, who, before her talk show, was a "biting standup comic." It was her talk show that made her seem more of a sweet, relatable, "mom" figure.

It was a 1999 interview with Tom Selleck where Rosie's "Queen of Nice" crown started to crack (via Today). She apparently went after the actor for his support of the NRA, and it started this new public perception of O'Donnell that Vulture labeled as an "overbearing, angry lesbian." According to Distractify, "The Rosie O'Donnell Show" ended in 2002 due to contracts ending and poor ratings. O'Donnell also said she wanted to spend more time with her family. 

In 2015, O'Donnell went through weight loss surgery and left The View

Rosie O'Donnell would make a return to daytime television in 2006 when she co-hosted "The View," but her time on the show would be short. In 2007, she left after not being able to commit to a contract, according to ABC News. However, according to Entertainment Tonight, O'Donnell had a tumultuous time on the show, often clashing politically with co-host Elisabeth Hasselbeck. She would continue her "angry" persona in the media. 

In 2015, O'Donnell tried coming back to "The View" again, but couldn't make it work. According to Variety, O'Donnell claimed it was "the end of her second marriage" that caused her to step away. However, it was reported her reputation as "demanding and sometimes abrasive" was also a factor. 2015 was supposed to be a comeback year for O'Donnell, who also had a huge weight loss transformation. According to ABC News, the comedian underwent gastric-bypass surgery "after having a heart attack and nearly dying." She said that despite losing more than 50 pounds, she still didn't feel "beautiful." She said that the surgery was more about her health than anything, and her heart attack caused her to refocus on a less stressful life. By quitting "The View" and spending more time with her family, O'Donnell could get back to healthy living. 

O'Donnell now sports a gray look and is set to return to Showtime

In recent years, O'Donnell has focused more of her attention on charity work. At the beginning of the pandemic, she raised $600,000 for the Actors Fund doing a special one-off episode of "The Rosie O'Donnell Show" (via Oprah Daily). 

The 59-year-old actress also now sports chic gray locks that she grew out for her role in Showtime's "SMILF." According to Today, O'Donnell actually had trouble getting her gray hair to grow and had to have it dyed. When asked whether or not she would be keeping the grays, O'Donnell said she wasn't sure, but it seems from her Instagram that she's still sporting the look.

O'Donnell is also returning to Showtime with the show "American Gigolo" where she'll play a detective investigating an open-and-shut murder from 14 years ago, according to The Hollywood Reporter. Could this be the triumphant return of O'Donnell that fans have been hoping for?