Rosie O’Donnell Is Still a Fan

In the opening scene of Showtime’s new “American Gigolo” series—a modern-day remake of Paul Schrader’s 1980 erotic thriller about a high-end male escort who is framed for murder—Rosie O’Donnell offers a distraught Jon Bernthal a soda and a stick of gum. Bernthal, in the lead role originally played by Richard Gere, has landed in jail after waking up next to a dead woman with a bloody knife in his hand. O’Donnell, playing the no-nonsense homicide investigator Detective Sunday, is trying to butter him up before coaxing him to confess. Her deadpan Long Island accent adds a touch of folksiness to the scene, but it is clear that she means business. O’Donnell’s run in “American Gigolo” is just one of several supporting roles she has taken on recently in reboots, including as a surly bartender in the Amazon Prime Video adaptation of “A League of Their Own” and as an insecure newcomer in Showtime’s “The L Word: Generation Q.” Her reëmergence as an edgy presence in nostalgic remakes feels like a cheeky nod to her nineties mythos as the Miss Congeniality of daytime television–and to how far she’s migrated from that rosy reputation in the time since.

The erstwhile O’Donnell—the Koosh-ball-tossing, red-blazer-wearing, giggly, gushy host of “The Rosie O’Donnell Show,” which aired on ABC from 1996 to 2002—was the one I watched every day growing up when I came home from school. Her effusive “Queen of Nice” persona was arguably the blueprint for a certain kind of aggressively cheerful, unabashedly dorky hosting technique. (You can draw a distinct line from O’Donnell’s hugs and sing-alongs to Ellen DeGeneres’s cringey dancing, or James Corden’s “Carpool Karaoke,” or Jimmy Fallon’s aw-shucks party games with celebrities.) O’Donnell’s infatuation with show biz—always a central theme on her show—began early on, when she was a child in Commack, New York, dreaming of being on Broadway. (She ultimately got there, three times.) She lost her mother to breast cancer at the age of ten and threw herself into becoming the class clown. After graduating, she enrolled in college but ended up dropping out to try her hand at a standup career. In the early nineties, she moved from the clubs to the screen. She was a staple sidekick in Hollywood—she played the tomboy Doris Murphy in Penny Marshall’s “A League of Their Own,” and Meg Ryan’s quippy best friend in “Sleepless in Seattle.” Her talk show, where she babbled about her love of Broadway and broadcast her crush on Tom Cruise, rocketed her to another level of fame, and by 2001, she told me, ABC was offering her “insane” money to stay on the air. But, she said, after 9/11 happened she felt that she could no longer pretend to be happy all the time, and she exited her contract. (She also cut ties with the publishers of Rosie magazine, a move that led to high-profile legal battles.)

After leaving the confines of network television, O’Donnell seemed eager to speak openly to the public about her life. She came out as gay in 2002, during a standup set, and started a gay-family-vacations business with her then wife, Kelli Carpenter. (The pair has since separated but has four children together; O’Donnell adopted a fifth, in 2013.) “Celebrity Detox,” a candid memoir about her frustrations with fame—complete with angry poetry—was published in 2007. Since then, O’Donnell seems to have involved herself in one kerfuffle after another as a kind of notorious loose cannon, on both television and social media. She joined the cast of “The View,” twice, and began a feud with her co-host Elisabeth Hasselbeck. She got into hot water for expressing anti-Catholic sentiments, for criticizing the Iraq War, and for engaging in a flame war with Donald Trump that continued through his Presidency. She has also found herself issuing a string of public apologies for making offensive offhand comments, including, most recently, in a TikTok video that she posted after meeting the actress Priyanka Chopra and mistaking Chopra’s parentage.

O’Donnell told me that she sees talking without a filter on social media as “a way to live authentically.” It may keep getting her in trouble, but for now she remains logged on. We also spoke about her early days in standup, her talk-show years, and “A League of Their Own” then and now. Our conversation has been condensed and edited.

How did you get roped into “American Gigolo”? Were you a big Paul Schrader fan?

No, not at all. In fact, I barely remembered it. I remember that it was cute naked boys, and a lot of sex, which made me uncomfortable in the year 1980. I was graduating high school. I was not a fan. But my agent called me and said that they were doing this with Jon Bernthal—and I am a fan of his work—and that it was being done by David Hollander, and I was a huge fan of “Ray Donovan”!

My agent told me, “You got an offer. You don’t have to talk to the director, you don’t have to read with anyone, you got a straight offer.” That’s the first time that’s ever really happened.

Really?

Yeah. I had to audition for “I Know This Much Is True.” Because Derek [Cianfrance], the director of that, doesn’t make you do the script, but he just wants to talk to you. So I had to sit and talk to the director. But I’ve never had someone call and say, “Here’s the offer.” And it was written for a man, because it was played by Hector Elizondo in the original movie. So I don’t know what deep fans the “American Gigolo” original has, but I may annoy some people. You never know.

It does feel like if you are on TikTok or any kind of social media now, you’re constantly offering yourself up for people to be upset at you.

I can see that. But I think for me it is such a way to live authentically. There was always a problem that I had being on my show, when I’d walk down the street in New York City. Everyone knew me, and I’d look at the magazine rack on the street and I’d go, “Oh, look, Rosie O’Donnell is on the cover of Newsweek.” But I wouldn’t think, Me.

There was a separate Rosie that you felt was a character that you were playing?

No, not a character. It was as authentic as I could be at the time. “Will and Grace” wasn’t on. “Brokeback Mountain” hadn’t happened. So much has happened in thirty years within the L.G.B.T.Q.I.A. community.

I want to go back even further, all the way to Long Island.

Commack, Long Island.

What was it like where you grew up?

It was the suburban American Dream. We were the first families into the houses in 1965. All those houses were built in Long Island with government subsidies, and they all sort of looked alike. My father was raised in a tenement. He used to tell us about the rats crawling up the curtains. And here he was with a piece of land, a quarter of an acre, and a six-bedroom house. We played kickball every night. It was, looking back now, a very innocent time.

And you were popular. Or so I read.

I was popular, yes. I was very funny, and I was very interested in getting the teachers to laugh. I didn’t want the other kids in the class to laugh at the teacher. I wanted to make the teacher laugh, and I did. I got a tremendous amount of love from the teachers in my life. One of them, Pat Maryville, really took me in and mothered me. She died a few years ago of breast cancer, as well as my mom. My first mom died of breast cancer [when I was ten years old].

That must have been hard.

I had one middle-school teacher who didn’t know what had happened or what was going on. My grandmother, who lived with us, was quite sick at this time, too. That teacher asked me, “Roseann, why didn’t you do your homework?” And I just said, “I don’t know. I didn’t have time.” He went, “That’s it. Give me your mother’s phone number.” And silence fell over the class. My heart started pounding, and he’s, like, “What is your mother’s phone number?” and “What is your mother’s name?” I didn’t answer, and he finally stopped asking, but then the kids were passing notes that said, “He doesn’t know her mom is dead.” I saw that and ran out of the school, and I ran home, but the doors were locked. So I went into my neighbor’s house, through the basement window, and I stayed in there until after dark, and they couldn’t find me.

And then I wouldn’t go back to school for a week. The principal of the school, I think her name was Rena Bologna, came to my house and talked to me about how her mother had died when she was younger and she understood, and so I ended up going back. And this teacher, Pat Maryville, heard that story. She was twenty-seven years old, she was a pretty new teacher, and she was engaged to the band teacher. She asked for me to be her student teacher. Every day, I had forty minutes alone with this woman, and she really taught me how to love. She was the first person to say “I love you” to me. We’re not an “I love you” family, or we weren’t when I was a kid on Rhonda Lane.