Rosie O’Donnell on Her New Show ‘SMILF,’ the Movie Role She Still Wishes She Landed, and Dating Again in Her 50s

Comedian tells Howard she’s in love with her new girlfriend, even if she doesn’t know much about Barbra Streisand

November 6, 2017
Photo: The Howard Stern Show

Motherhood is a subject matter Rosie O’Donnell is an indisputable expert on, so it’s no wonder why she decided to take on her role in the new Showtime series “SMILF.” On Monday, Rosie stopped by the Stern Show and talked to Howard about playing Tutu, a mentally-ill woman who loves her daughter and grandchild but isn’t able to fully form a healthy relationship with her family, no matter how hard she tries.

“SMILF” is based on a previously released short film by the show’s star, Frankie Shaw. When Rosie saw it, she instantly knew she wanted to work with her. “It was so profoundly feminist and intelligent,” Rosie said of the short.

Shaw not only stars in “SMILF” alongside O’Donnell, she also writes and executive produces the series. “She’s the real deal and it inspired me so much to be around her and watch her run a set,” Rosie told Howard. “I feel almost like her mother … I’m really proud of her.”

Since Rosie knows firsthand the effect depression can have on an individual, she gave a note early on for how her character should look on camera. “The first thing I did was I asked if we could shoot with no makeup for me. Like, none at all,” Rosie said. According to Rosie, self-care is one of the first things to go in someone dealing with depression and she wanted Tutu to reflect that.

“I just want it to be raw and real,” Rosie recalled telling Frankie.

Another raw and real role that Rosie still wishes she had landed herself was the lead in the film “As Good as It Gets.” Helen Hunt went on to win a Best Actress Academy Award for her portrayal of Carol Connelly, but Rosie said the character was very different when she was up for the part.

“It was for an overweight, kind of slovenly waitress who had a special needs child. I was like, ‘Oh my God, this is gonna be me,’” Rosie said with a laugh. “I really wanted that role.”

Rosie also famously didn’t get to play the part of Elaine Benes on “Seinfeld,” but on Monday she told Howard she wasn’t envious of Julia Louis-Dreyfus. She can still recall her audition in front of Jerry Seinfeld, Larry David, and Carol Leifer and admitted she had no clue the show would be as big a hit as it would soon become.

“He was just another comic guy that I knew and it was a pilot, so, who knew?” Rosie said of Seinfeld.

In addition to her new TV show, Rosie also has a new girlfriend that she told Howard she’s very much in love with. “It’s the first time I have dated someone younger than me and it’s a very trippy thing,” Rosie revealed.

Her girlfriend is a police officer in the Boston area and is 22 years her junior. However, their age difference hasn’t gotten in the way too much. “The one thing that she doesn’t know … Streisand,” Rosie told Howard, adding that she forced her to watch Barbra Streisand’s “Funny Girl,” one of Rosie’s favorite films. After the movie was over, her girlfriend simply remarked, “it was good.”

Rosie met her new lady friend at a charity event and at first thought she looked like a famous pop star. “She had very short hair. In fact, I thought she was Pink,” Rosie told Howard. It took a few times before Rosie agreed to go out on a date with her, but it didn’t take long for the two of them to say “I love you” to one another.

“We’re lesbians. That’s like week two,” Rosie joked.

Since they’re in love, Howard asked if Rosie would ever consider getting married again. “I will not, ever,” she replied. “For me, being 55, I just think I would rather stay in it for love and not have to deal with lawyers if, God forbid, it shouldn’t work out.”

See Rosie O’Donnell in “SMILF” Sunday nights at 10 p.m. ET on Showtime and for more information on Rosie visit