Years before Tom Cruise called Matt Lauer “glib” or Dakota Johnson reminded Ellen DeGeneres that she was, in fact, invited to her birthday party, Tom Selleck and Rosie O’Donnell set the stage for one of daytime TV’s tensest moments.
It was May 1999. Just weeks after the Columbine massacre. Although Selleck planned to visit The Rosie O’Donnell Show to promote his new romantic drama, The Love Letter, he was also then the literal poster boy for the National Rifle Association. What started as chitchat with O’Donnell about his onscreen romance quickly turned into an argument over the Second Amendment.
“I didn’t come on your show to have a debate. I came on your show to plug a movie,” Selleck sniffed after more than six minutes of gun talk and claiming O’Donnell was “questioning” his humanity. As the audience clapped awkwardly and Selleck exited the studio, he passed child actor Jake Lloyd waiting in the wings, there to promote his role as young Anakin Skywalker in the new Star Wars. “Watch out, kid,” supervising producer John Redmann recalls Selleck warning the panicked 10-year-old.
America was as shocked as the tiny Phantom Menace star. First, there was the obvious uneasy jolt of watching a host spar with an annoyed guest on live TV — and beyond that, the fact that this chilly showdown had occurred within the usually warm haven of 30 Rock’s Studio 8G, a cozy nest of Koosh balls and crafting, where celebrity interviews were eternally peppy and light. While O’Donnell’s outspoken political takes would later be expected during her tenure on The View, this was a different era entirely.
This was The Rosie O’Donnell Show.
In the 25 years since The Rosie O’Donnell Show debuted in June 1996, our expectations for talk shows and the people who host them have shifted. New daytime ventures have come and gone, from endless brief stints by celebrities to DeGeneres, who is packing up her sweaters after 19 seasons following allegations of workplace toxicity and declining ratings. And now, a former Texas cocktail waitress turned music superstar is poised to become the genre’s new queen.
Today it’s assumed that every host will act like a PR-friendly fan, and every fan will generate friendly PR. Segments are concocted to go viral, and viewers who never even watch network TV engage with bite-size clips in their feeds. But when America was still running on dial-up, O’Donnell seized on a prescient spark. Without social media or YouTube, she managed to become a benevolent influencer and relatable best friend to the masses. While other hosts fired off invasive questions, O’Donnell cheerfully lobbed projectile Koosh balls and seemed, for a time, determined to combat cynicism with a tidal wave of positivity. Years before DeGeneres would become known as “the ‘be kind’ lady,” Newsweek ran a cover story on O’Donnell after her talk show’s premiere that branded her with the splashy tagline: “Queen of Nice.”
“I thought, Oh, this is gonna bite me in the ass,” O’Donnell tells Vulture.
In the mid-’90s, the world knew O’Donnell as a stand-up comic and affable, Long-Island-accented actor in films like Sleepless in Seattle and A League of Their Own. After shooting Harriet the Spy in Toronto in 1995, however, O’Donnell became distraught that her infant son, Parker, clung to their housekeeper at the end of each long day. She was eager to find a New York–based job with regular hours, and a daytime talk show seemed the logical, stable choice.
But the programming landscape was, as O’Donnell describes it, “a thug festival.” Jerry Springer, Ricki Lake, Maury Povich, and a slew of other daytime hosts supplied endless conflict TV — in 1995, Scott Amedure had been murdered in the fallout from his Jenny Jones appearance — and she wanted no part of that. And though The Oprah Winfrey Show had prestige and ratings, it was at the time focused on dramatic, real-world issues.
Instead, at 34 years old, O’Donnell was given the keys by Warner Bros.’ Telepictures production company to oversee a then-radical daytime-television experiment. Merging comedy, variety, late-show, and game-show formats, she would bring together her favorite elements from classic interviewers like Merv Griffin and Mike Douglas, tie in song-and-dance numbers, add in arts-and-crafts time, and crank up the audience participation.
Stationed down the hall from Saturday Night Live at NBC’s Rockefeller Center studios, The Rosie O’Donnell Show premiered in June of 1996 and brought a welcome burst of late-night star power and glitzy fanfare to daytime. While her contemporaries pretaped their episodes, O’Donnell walked the tightrope of live TV for the show’s 10 a.m. broadcast in New York. “One of the things Rosie wanted to do was, ‘Let’s do it like it’s theater,’” recalls Bernie Young, O’Donnell’s manager since the 1980s who eventually became executive producer of her talk show. “Theater’s her baby. You don’t get a second chance. It’s one shot.”
“It felt like we were going to the clubhouse every day.”
Interns placed a Drake’s Cakes snack at every seat before the studio audience filed in each Monday through Thursday, hyping up the 180 guests on sugar as filming got underway. Each show opened with an ecstatic fan introducing the host, giving non-media-trained civilians the mic and adding a terrifying thrill of unpredictability from the top of the hour, as O’Donnell burst through the curtain and engaged with Justin from Virginia or Kathy from Toronto.
In typical late-night fashion, O’Donnell held court behind a stately desk next to the house band, John McDaniel and the McDLTs (a play on the now-defunct ’90s McDonald’s menu offering), and started each show with the chuffa, which saw her riff about the day’s headlines and activities of the night before with McDaniel, her old pal whom she used to belt show tunes with at parties.
“It felt like we were going to the clubhouse every day,” McDaniel says of filming, “and she was the president.”
Before Jimmy Fallon and Andy Cohen fawned over their celebrity guests, O’Donnell embodied the idea of the talk-show host as the ultimate fan. Often giddy with excitement, she’d tote out her own memorabilia, regale guests with tales of how many times she’d seen their movies, and join them in off-the-wall games. “The difference between Rosie and Dave [Letterman],” Entertainment Weekly wrote in a 1996 review, “is that O’Donnell actually likes things — her guests, other television shows, and living inside her own skin.”
That authenticity resonated across America. With sky-high ratings, The Rosie O’Donnell Show quickly became the first stop on celebrities’ press tours, and a parade of legends like Prince, Madonna, David Bowie, and Mary Tyler Moore rotated through the chairs alongside Aaliyah, JTT, Britney Spears, and the Pepsi girl. They felt safe knowing their visits would stay upbeat and void of any mention of scandals that may be happening outside the studio walls.
When Cher stopped by to play what amounted to a pre-digital, rudimentary version of “Heads Up,” she nervously asked O’Donnell what would happen if she lost.
“Have you seen this show?” O’Donnell fired back. No one ever lost.
“It was such a vital booking for these celebrities that they came ready to play, and Rosie, as the ultimate fan, sold their project like no one else could,” Redmann says. “It was lightning in a bottle.”
The show’s appeal spanned beyond traditional daytime-talk-show demos. In addition to stay-at-home moms, grandmothers loved Rosie, gay men loved Rosie, and, perhaps above all, kids loved Rosie. Many markets syndicated her show in the afternoons, making it the perfect after-school treat, and she catered to children by reading kids’ jokes on air and welcoming everyone from the young cast of Harry Potter to the national spelling-bee champion. A motorized footstool occasionally popped out from the interview chair to accommodate the shortest of legs.
O’Donnell also routinely put Broadway front and center, inviting casts to perform elaborate numbers, and her endorsement could make or break a struggling production. When the Titanic musical opened to mixed reviews, she brought the cast on to perform, and its box-office sales instantly multiplied, according to the New York Times, which declared, “Rosie O’Donnell has become to Broadway what Oprah Winfrey is to books.”
For viewers in small-town America who might otherwise never see a Broadway performance, it was eye-opening.
“It was a two-way street,” O’Donnell’s former assistant turned show writer, Caissie St. Onge, says. “She was exposing people throughout the country to live theater, but also she was pumping lifeblood into New York theater.”
But for O’Donnell, the ultimate guest was Barbra Streisand. No detail was too small to ready the stage for Streisand’s emotional full-episode appearance in 1997. To accommodate the singer’s famed “good side,” O’Donnell instructed the crew to flip the set weeks before her arrival so it wouldn’t be obvious they were doing it just for Streisand. A florist’s worth of flowers filled the halls of 30 Rock, and interns were tasked with picking out just the blooms in Streisand’s favorite colors to include in the set décor. When the host and singer finally met, both women sobbed.
“I can’t really watch that tape. Because even though that seems like a really big emotional thing, it’s just the tip of a big, big, big emotional thing,” O’Donnell says. “Who would ever think that you could meet the person who you would dream of every single night? If they had had the internet when I was a kid, and there was a possibility that Barbra Streisand would read one of my tweets, I would have never gone to school. I would have stayed home and tweeted, ‘Barbra, please, I love you more than anyone else does.’”
On the other end of the spectrum was Donald Trump, whom O’Donnell viewed as a hack and refused to interview over the course of the show’s six seasons. “They asked many times,” she says. “The only time I allowed him to come on was to be a sweeper for sweeps,” a gimmick that involved celebrities cameoing to literally sweep a broom across the stage during ratings-sweeps weeks. “We had everyone from the Dunkin’ Donuts guy to Val Kilmer, and we let Donald Trump be one of those people — but I didn’t have to talk to him.”
Not every guest who warranted more airtime went off without a hitch. O’Donnell alleged on Watch What Happens Live that Bill Cosby once sexually harassed a producer and Leif Garrett was asked not to return to the show after injuring himself in the greenroom. (Reps for both men have denied the incidents.) Whitney Houston bailed on a 1997 performance 45 minutes before airtime. And when Donny Osmond appeared on the show during its very first week, O’Donnell brought out paraphernalia amassed from her time as a childhood fan, only to have Osmond promptly crack a joke about her weight, saying a helicopter wouldn’t be able to lift her.
“I almost thought I was having a dream or something,” she says now. “Don’t tell me this guy who I just professed my love for is going to come on my show and call me fat.” So O’Donnell did the only logical thing: invite Osmond back to beg for forgiveness and sing “Puppy Love” to her while wearing a dog costume.
She had a knack for doling out justice on air. When a Scope poll named her America’s least-kissable celebrity, she finagled it into an opportunity to partner with mouthwash competitor Listerine, who would donate $1,000 to O’Donnell’s charity for disadvantaged kids every time she got a kiss from a celebrity guest. In exchange, O’Donnell belted out priceless ads: “Remember that Listerine kills the germs that cause bad breath,” she said on air. “And remember, just say nope to Scope.”
Outside of possibly Oprah’s “Favorite Things,” which was at the time just gearing up, O’Donnell’s endorsement was the most prized shout-out on TV. Anything she mildly praised became a hot commodity, and audience members regularly left the show with new Game Boys, theater tickets, and more. She was almost single-handedly responsible for the Tickle Me Elmo craze of Christmas 1996, and brands were desperate to get into her good graces. So she made a practice of plugging their products in exchange for their donations to various groups in need.
“You could really use your muscle like the mafia does, but for good,” O’Donnell says. “You could go, ‘Well, listen, I’d love to talk about your new product. If you were able to send 300 kids the new Elmo toy, we’d be able to do this for you.’ And that’s how we did it. We bartered for charity.”
“She was not the queen of nice. She was the queen of fair.”
As predicted, that “Queen of Nice” persona did come back to bite O’Donnell. During the early seasons, the show experienced a high turnover of directors, and the executive-producer role changed hands three times before finally falling to Young. Some outsiders took this as a sign that O’Donnell was an insufferable boss, a villain masquerading behind a “nice” on-air shtick. Staffers who spoke to Vulture confirm it was a cutthroat, competitive environment, and O’Donnell was known to expect perfection from her team.
“She was not the queen of nice. She was the queen of fair,” says Corin Nelson, who graduated from celebrity booker to supervising producer on the show. “She was tough because she cared about the show. If someone had to work late, she was also the same person who would then put a bottle of champagne on that person’s desk to congratulate them that they’ve done a great job.”
Still, several of the same producers and writers who succeeded at Rosie went on to work at The Ellen DeGeneres Show, including current Ellen executive producer Andy Lassner. And one Hollywood Reporter article linked Buzzfeed News’ reports of a toxic culture at Ellen and TMZ to being indicative of a larger, decades-long Telepictures issue that included executive Jim Paratore’s reign over The Rosie O’Donnell Show.
“Our staff and the situation with our staff was nothing like that,” O’Donnell says of the Ellen correlation, while McDaniel adds, “I’m not surprised by much, but I was surprised to read that. I just don’t think it’s a fair comparison at all.”
All of the sources who spoke to Vulture, including those who spoke on background, praised The Rosie O’Donnell Show and particularly O’Donnell for leading by example and treating her staff with generosity — even if she wasn’t always in a perky, camera-ready good mood.
“She had the most to lose and she had to rehearse a lot in the morning, which wasn’t her favorite,” says Judy Gold, who served as a writer and human-interest producer on the show. “But there was this unspoken rule that we’re not going to fucking be mean to people.”
At O’Donnell’s behest, staffers received paid summers off between seasons (a rarity in TV), generous maternity leave, and access to a free on-set day-care center for all working parents (completely unheard of at other shows). When O’Donnell learned St. Onge was stressed over only being signed per 13-week show cycle, she had her contract changed to give her job security for the next two years. O’Donnell notes that Warner Bros. was concerned such perks would “set a precedent,” and says she countered, “I don’t really care. If you want me to do the show, you have to be kind to the people who work here making you millions of dollars.”
O’Donnell had made a point to fill her staff with women in leadership roles, and upward mobility saw interns become producers, assistants become writers, mid-level producers become department heads. Decades later, many of those who succeeded on O’Donnell’s show went on to run empires of their own (among others: Redmann, who later oversaw ten years of The Talk; St. Onge, who served as showrunner for Busy Tonight; Nelson, who was an executive producer and showrunner on Chelsea Lately and The Queen Latifah show; Jason Kurtz, a talent assistant at Rosie, who is now an EP on The Drew Barrymore Show; and Amy Weinblum, who began as an intern at Rosie and later became Oprah’s chief of staff). J. Ryan, a straight man who worked as a production assistant on the show when he was a teenager, recalls some of the crew teasing him that he only got the gig because he was “effeminate,” explaining that “the rumor always was that if you wanted to work for Rosie, you either had to be a woman or a gay male.”
They weren’t entirely wrong. As a gay woman running a talk show in the very much still white, straight, male TV milieu of the ’90s, O’Donnell confirms she sought to hire other women and “as many out gay people as we could.”
But while O’Donnell was never in the closet per se, she didn’t publicly discuss her own sexuality. Her schoolgirl crush on Tom Cruise became an ongoing shtick on the show, and she’d punctuate her declarations of love for him with a blast of The Who’s “Tommy, Can You Hear Me?” using the radio-DJ technology at her desk. Theirs was a platonic love affair for the ages. When the movie star eventually appeared as a guest, he fretted over the flowers he brought for her backstage. “I remember him saying, ‘I got her these roses. Do you think she’ll like them?’” Nelson says. “And we were all like, ‘Are you kidding me?!’”
(To this day, O’Donnell says, Cruise sends her flowers and a coconut cake on her birthday: “He’s an unbelievable mensch-y guy.”)
She wasn’t lying about having a nonsexual crush on Cruise: Her fantasy was to have him cut her lawn and hand her a glass of lemonade. But she also felt she couldn’t openly come out. While it was no secret to the staff of The Rosie O’Donnell Show that she was a lesbian, Telepictures cautioned O’Donnell and the otherwise openly gay McDaniel against mentioning their partners in their daily banter.
“I used to say, if Middle America only knew that this show was put on by a bunch of gay people and their friends, we would change the world,” says Gold. “We’re entertaining you like you’ve never been entertained before — and we’re all gay, gay, gay, gay, gay! And if we’re not gay, we’re theater geeks. It was sort of a powerful feeling.”
The closest O’Donnell came to publicly discussing her sexuality happened when DeGeneres appeared as a guest in 1996. This was months before DeGeneres’s “Yep, I’m Gay” Time cover, but rumors were already swirling that her Ellen sitcom character was going to come out. So O’Donnell devised a plan with her fellow comedian backstage: They would perform a bit where DeGeneres revealed her character was actually “Lebanese” and liked “baba ghannouj” and “Casey Kasem.” “Hey, wait a minute. I’m a big fan of Casey Kasem,” O’Donnell replied on air. “Maybe I’m Lebanese!” The audience cheered.
“I did that in solidarity with her as another gay woman,” O’Donnell says. “I think that was a wonderful moment on the show, and a real true moment. The intent of it was simply to stand together with someone else.”
It would take another six years, the success of Will & Grace, and the knowledge that her own show was definitively ending for O’Donnell to publicly come out in 2002, when she used the revelation to try to help reverse a Florida law that barred gay people from adopting children. “At the time in our culture, I didn’t think it was possible to come out as an entertainer and still work and be accepted,” she says. “I really didn’t.”
“People still write me and say, ‘You ruined it!’”
The Rosie O’Donnell Show had catapulted O’Donnell into a new, bizarre level of stardom and scrutiny. With a daily audience that could at times top 5 million, viewers felt like they were part of O’Donnell’s extended family. After all, this was the woman who grew out a chin hair long enough to attach a bead to and proudly show off on TV.
“There was no barrier when I was out in public,” O’Donnell says. “That’s been my whole life in show business: Everyone thinks they know someone just like me. Everyone is like, Oh my God, you’re just like my cousin, Elizabeth. Or, You’re just like my friend, Eileen. Everybody found me relatable.”
Perhaps that’s why she didn’t think her candid comments during that infamous 1999 Selleck incident would have such an impact. “Was that okay?” she recalls asking after the episode wrapped. It’s not like she had been the only one to take issue with Selleck’s NRA campaign. Even before Columbine, Jon Stewart blasted the “celebrity spokes-nut” on The Daily Show. But unlike Stewart, O’Donnell was a woman. A woman with a platform that reached every crevice of wholesome America. “The right-wing hate machine sicced their dogs on me. They would send us all these postcards, so we would chop them up and use them for confetti,” O’Donnell says. “And I would say, ‘From now on, the confetti is thanks to the NRA!’”
Behind the Crossfire-esque tussle was a personal shift for O’Donnell, who was by then the mother of two young children, soon to adopt a third. Columbine had deeply affected her, and she was newly on medication to battle depression. The relentless fame was also oppressive.
“Your whole life is spun out in a way that you had thought of but really could not even come close to imagining,” she says. “‘Superstardom is close to postmortem.’ That’s what Eminem wrote. And I think that in a way, it’s like having some sort of condition or illness while you’re in the midst of it.”
A few months after the Selleck interview, in a pre-Wikipedia, largely spoiler-free world, O’Donnell revealed Fight Club’s twist ending on air just as the movie opened nationwide. She says she merely wanted to show that the gun-heavy flick had an inferior twist to that of The Sixth Sense, but the damage was done. “Courtney Love [Edward Norton’s then-girlfriend] wrote me and said that Brad Pitt was never going to talk to me again because I ruined it,” O’Donnell says. “People still write me and say, ‘You ruined it!’”
Increasingly, O’Donnell was finding it impossible to remain politically neutral in the public eye. In 2000, fed up with watching the Republican National Convention on TV, she decided to go fishing, only to stab herself in the finger with a knife while cutting price tags off a fishing pole, resulting in multiple surgeries and a staph infection that caused her to miss weeks of filming.
“I’m so glad that I was not on TV when we entered the Iraq War,” she says. “I think that would have been really bad for me emotionally to have to be on television every day when that kind of panic ensues, when there are things that I can’t control in our world.”
She was on TV the morning of September 11, 2001. That day, staff at The Rosie O’Donnell Show were gearing up for an hour-long special with the cast of Everybody Loves Raymond. Instead, they watched in horror as the monitors in the studio control room showed the second plane hit the World Trade Center, and Katie Couric relayed the grim news from Today just a few floors down. (O’Donnell would later espouse her own theories around the attacks.)
“The next day we got out of New York somehow, and I was like, I’m never coming back,” O’Donnell says. “It was uncontrollable, for people who have anxiety and depression issues — I remember telling Jim Paratore that I was never coming back to the show. Because when things like this happen, what does it matter? It was very dark.”
But just one week later, The Rosie O’Donnell Show was back on the air. Sporting an FDNY sweatshirt and bringing on local guests like Mario Cantone and Liza Minnelli, O’Donnell encouraged her viewers to return to New York and, of course, support Broadway. She also showed pictures of her children to the audience for the first time, after years of fiercely guarding their privacy. “I remember thinking your life could be over tomorrow,” she says. “Let people see who you love.”
Still, as house-band bassist Tracy Wormworth says, “That was basically the beginning of the end of the show.” Eight months later, O’Donnell signed off from Studio 8G for the last time on May 22, 2002. With a blowout Broadway send-off and a special taped appearance by Cruise to toast her with that long-awaited lemonade, it was a bittersweet farewell.
From a business standpoint, the show could have continued apace for years. But O’Donnell was spent. Caroline Rhea was brought on to guest-host the remaining season-six episodes and then took over with a short-lived talk show of her own.
“People like Ellen and Oprah, they are long-distance runners. They seem to have an endless resource. I don’t have that,” O’Donnell says. “They kept offering me more money and more money and more money. But my mom died at 40, and I was 39. I wanted to go coach my kids’ baseball games and participate in my family in a way that having that kind of show prevents you from doing.”
After a four-year break, she’d go on to join The View and later helm the fleeting The Rosie Show on OWN, both fostering plenty of drama and showcasing a different persona than the one viewers had come to know. “You can’t go backwards. I think that’s what we find,” she says now. Twenty-five years after The Rosie O’Donnell Show debuted, O’Donnell looks back on that era as an intense “height of my life that will never be replicated.”
And she’s okay with that. O’Donnell spoke to Vulture via Zoom from her home in New Jersey, clad in her trusty Hamilton hoodie and surrounded by the crafts she’d been working on throughout the pandemic. In March 2020, she revived The Rosie O’Donnell Show for a one-off virtual benefit, featuring dozens of Broadway stars raising money for the Actors Fund. Following the event, O’Donnell’s mentions were flooded with fans begging her to revive the talk show. But a full-scale reboot is unlikely; while she recently started uploading clips of her old interviews to YouTube, she’s focused on acting again and admits she’s out of touch with the current pop-culture landscape.
“I had a People magazine at an airport once, literally didn’t know one person in it,” the now 59-year-old says. “I sit in here and I craft and I blast Broadway music, and I feel a little bit better.”
Yet the spirit of The Rosie O’Donnell Show still ripples across daytime and late night alike. It’s in DeGeneres dancing with her audience and Kelly Clarkson putting guests at ease with a wide grin and self-deprecating story; in Cohen’s rapid, gleeful recall of celebrity minutia and Fallon’s low-stakes games.
For her part, O’Donnell is happy to have passed the torch. Gone are the days when she’d be surrounded by expectant fans the minute she left her home. Now, the occasional sighting comes in the form of quiet recognition from other women perusing the craft-store aisles alongside her.
“They see me and they wink at me,” O’Donnell says. “And I wink back.”