Janet Jackson, the 10th and youngest child of Joe and Katherine Jackson, was born into the entertainment business and got her first taste of solo success as an actress, starring on Good Times and then finding roles on Diff'rent Strokes and Fame. But that didn't mean the path she'd chosen was easy, even if she had a few brothers blazing the trail ahead of her.
As a Black performer, "there is a double, triple standard that she had to live up to, at a very impressionable age," notes Cathy Hughes, founder and chairwoman of media company Urban One Inc.
In old interview footage, Jackson talks about going into wardrobe on Good Times at the age of 11 and having her chest taped down, and soon after was told to lose weight. And in a separate chat on Larry King Live, she reveals her childhood nickname "Donk" (which her brothers called her) was short for donkey, from supposedly having "a body shaped like a donkey." Jackson says, "I got teased a lot as a kid."
Michael Musto, a former columnist for the Village Voice, recalls Jackson telling him when he interviewed her in 1984, "'I wouldn't mind doing a video with Michael, if they have any parts for chubby girls.'"
The release of 1993's Janet marked the start of a new creative era for the Grammy winner, who had largely been known for fiery danceable hits like "Nasty," "Miss You Much" and "Rhythm Nation" and her combat-meets-power-suit-inspired style. But slow and sensual went the beat and off went her shirt for the iconic Rolling Stone cover featuring a topless Jackson, her then-boyfriend Rene Elizondo cupping her breasts from behind, his hands the only part of him that were visible.
But what do you know, there was a culture war raging at the time, from Republican Vice President Dan Quayle's disdain for Murphy Brown becoming a single mom and the increasingly influential Parent Television Council's concern that violence, profanity and explicit sexuality was going to become the norm in the media, to Clinton-era Second Lady Tipper Gore pushing for parental advisory warning labels on music.
"Janet is walking in the middle of that," remembers music journalist Touré.
Jackson's association with Justin Timberlake dated back to 1998, when she tapped up-and-coming boy band 'N Sync to join her on The Velvet Rope World Tour. Timberlake is seen in multiple interviews from that time fanboying hard over Jackson. But nowhere does he seem more outclassed than when he and Chris Kirkpatrick are presenting Jackson with the inaugural MTV Icon honor in 2001 and Timberlake is comfortable playing the lascivious goofball.
"When things were first starting out for 'N Sync, Janet took us with her on the Velvet Rope Tour and taught us what being professional is all about," Kirkpatrick says. Cuts in Timberlake, "Yeah, like how to be fine."
Kirkpatrick begins, "We love Janet for a whole lot of reasons," and his mate cuts in again with, "Yeah, like she's fine."
And when Kirkpatrick extols the "coolest, most laidback groove" in the video for "That's the Way Love Goes," Timberlake can't help himself. "Yeah, she's fine in the video too!" he exclaims. "Fine!"
When Super Bowl XXXVIII rolled around, the NFL championship once again on CBS and fellow Viacom entity MTV producing the halftime show, the PTC was keeping its eyes peeled in the wake of Madonna kissing Britney Spears during the 2003 VMAs.
Current PTC President Tim Winter admits that they knew MTV was "likely to bring along the potential for risky, racy content, and we were mindful and very concerned about the family-friendly nature or lack thereof of that show because of MTV producing it."
Timberlake was a late addition to the halftime show lineup, a response to concerns—spelled out in a letter to then-NFL Commissioner Paul Tagliabue from Houston Texans owner Bob McNair—about the proposed talent, which at the time included Jackson ("the least concern," recalls Jim Steeg, director of NFL Special Events), Nelly, P. Diddy and Kid Rock. Tagliabue, too, remembers being on his guard due to the "misogynistic lyrics" in hip-hop. He spoke to CBS' then-chairman and CEO Les Moonves, who assured him everything would be fine, he'd make sure the show would be "first class and there'd be no problem," Tagliabue shares.
So when someone suggested adding Timberlake, Steeg thought it was a great idea—and they decided to make it a surprise.
In an interview, Jackson teased that there'd be "a special guest" joining her onstage. At a press conference, Diddy promised "some surprises I think, maybe, y'all will have to see," and an MTV release stated there would be "shocking moments."
Steeg, former MTV Senior VP Salli Frattini and Beth McCarthy-Miller, director of the Super Bowl XXXVIII Halftime Show paint a picture of a tight squeeze to get everything ready for game day.
McCarthy-Miller says they only had access to the field on the Thursday night before Super Bowl Sunday, so they ran through several full dress rehearsals at that time. Steeg recalls drawing up about two and a half pages of notes of concerns and recommended changes—and Frattini remembers receiving all sorts of notes from the NFL and CBS (including concerns about some of Nelly's and P. Diddy's lyrics and the NFL's worry that Kid Rock wearing an American flag might offend people, in a he's-disrespecting-the-flag-by-wearing-it way).
They had very little individual time with each artist, "especially Justin, because he was flying in from Europe," Frattini says. (He also flew to Los Angeles after rehearsal and returned to Houston that Sunday morning, landing 20 minutes before the halftime show started. A police escort assured swift passage to the stadium.) Originally, Jackson was going to be wearing a tearaway skirt and at the end of "Rock Your Body," to go with the line "gonna have you naked by the end of this song," Timberlake was going to rip that off, under which she'd be wearing a full jumpsuit.
That didn't work from a staging perspective, they all concurred.
In the meantime, Frattini says, "I looked at every piece of wardrobe along with someone from my standards and practices department, so that we were sort of legally looking at everything. I felt like we had delivered the messages clear."
Citing previous reporting, music journalist Alan Light recounts that Jackson's stylist Wayne Scot Lukas went shopping after the dress rehearsal, picking up, among other things, a sterling silver nipple shield in the shape of a sunburst, with a bar through the center, and then made some alterations to her outfit. (The show includes footage of a Janet-era Oprah Winfrey Show interview in which the host asks Jackson why she pierced her nipple, to which the singer replied, "For one, you get this great sensation." Winfrey responded with a resounding, "Hello!")
"We had no knowledge at all," Frattini recalls, shaking her head slightly, "of what might have been happening between Janet and her team."
Lukas told Capsule 98 in May, "It's been 17 years since the Super Bowl, and I get calls every single year to talk about it. I have stayed quiet and protective of Janet as my friend and my client. There is an unwritten privacy that you give to your clients and friends." (But in the interviews he has given, he comes down firmly on the side that Jackson was wrongfully vilified and screwed over by the various entities involved.)
Timberlake and Jackson met for a couple of minutes in her dressing room before showtime—and then the production got underway, native Texan Jessica Simpson kicking off the festivities with several college marching bands.
Steeg recalls thinking that MTV had disregarded a few of his notes, but at this point he's still referring to such things as sexy cheerleaders surrounding a crotch-grabbing Nelly for "Hot in Herre" (they did know the lyrics encouraged you to "take off all your clothes," right?) and Kid Rock's flag tunic (Tagliabue says his high school teacher daughter told him the head-banging rocker had totally "disrespected the flag" and she didn't know how she'd explain the NFL's lapse in judgment to her colleagues).
Jackson returned, emerging from underneath the stage, and performed "Rhythm Nation" with her badass squad of dancers. Then Timberlake joined her for "Rock Your Body," to wild applause.
"Justin came out, the song begins, they're rockin' it, they're doing the choreography as planned, and everything was scripted," Frattini recalls. "And then of course we come to the close and it's the final few seconds of the song." She pauses. "And that's just when everything went wrong."
Musto of the Village Voice echoed a lot of people in admitting, "I barely noticed."
Alas, enough people noticed nothing else.
Still, Frattini thought the first immediate phone call she received when the show was over was going to be a congratulations for how amazing it was.
Neither she nor McCarthy-Miller knew what "Did you see what happened?" even meant at first. But the director's stage manager, who also didn't know, told her that she had held out a blanket for Jackson to immediately wrap herself in off-stage (as previously planned) and the singer was crying.
Steeg asked Frattini if she knew that was going to happen, and she said no. "And he goes, 'I believe you,'" she says. Not until they rewound the footage and looked at the closeup and wide shots did they really see that nine-sixteenths of a second.
There was still half a Super Bowl to play, but the phones were buzzing and no one could talk about anything other than what they'd just seen—or thought they saw. The main questions were: Was that planned and, if so, why? For publicity for Jackson's forthcoming album, Damita Jo, due out that March?
Timberlake cryptically told CBS Sports' Pat O'Brien directly after the show, "That was fun. It was quick, slick, to the point, and enjoyed it. It was a lot of fun." When O'Brien commented, "You guys were getting pretty hot and steamy up there," the 23-year-old flashed a big grin at the camera and replied, "Hey, man, we love giving y'all something to talk about." And when correspondent Maria Menounos quipped that he had gotten "nasty with Miss Jackson," he smiled again and said, "Hey, it's every man's dream."
Meanwhile, Jackson had left the stadium immediately and no one from her team was answering their phones.
"If she had been there to sort of take the heat and talk about it, 'Hey, maybe it was a mistake'...She never said anything to us," Frattini laments. "Here we are trying to ask the person that this has happened to, 'cause it happened to her, and she was gone."
She says Timberlake told them it was "never meant to happen" and was "very apologetic," adding, "He manned up."
Frattini recalled being "a wreck" and crying afterward. "I felt betrayed," she says. "My instincts told me that there was a private conversation between wardrobe stylist and artist where someone thought this would be a good idea, and it backfired."
"Unforgiveable." "MTV Says It Was Punk'd." "I'm inclined to believe they planned it." "Wildly inappropriate." "Just say, 'I'm a trollop. I need attention. Buy my new album.'" "A patheticism on the part of Janet Jackson, who probably has seen the best days of her career."
Another female commentator noted that Jackson was 37, "almost geriatric in the age of pop music."
That's a sampling of the headlines and hot takes that dominated the news in the wake of Jackson's wardrobe malfunction (a term eagerly welcomed to the lexicon after it first appeared in the public apology from Timberlake's camp) as the scandal known as "Nipplegate" took its vicious shape.
At least one cartoon thought to make fun of the outrage, Tagliabue surrounded by scantily clad Dallas Cowboys cheerleaders while saying, "I was shocked, shocked to see all that sex in a Super Bowl Halftime Show."
And though so much was made of Jackson being nowhere to be found, she released a statement the next day (the first of several apologies), admitting that the decision to do a costume reveal was made after the final rehearsal and "MTV was completely unaware of it. It was not my intention that it go as far as it did. I apologize to anyone offended—including the audience, MTV, CBS and the NFL."
But too late, all of America's children had been irreversibly corrupted! (Or so the critical narrative made it sound.)
In a subsequent interview with Entertainment Tonight, Timberlake explained he'd gotten a call before the show and was told Jackson wanted to do this reveal. "Now I was under the impression that what was going to be revealed, in the costume reveal, was a red brassiere—a bustier, forgive me. And, you know, got in, didn't really have time to rehearse it. Got to the field, went onstage, was in the moment, and when what happened happened, all I could say was, 'Oh my god, oh my god.'"
"I don't feel like I need publicity like this," he added. "And I wouldn't want to be involved with this stunt, especially something of this magnitude."
New York Times reporter Rachel Abrams observes that, at the time, Jackson's apology was considered "insufficient," while Timberlake was viewed as being much more "forthcoming."
Or as her colleague Jenna Wortham, who sensed Jackson looked truly shocked when it happened, puts it, "What's so painful about that moment is, everything Janet had been working for and towards, building up to in her career, was just taken away. In that moment. By this white man!"
Abrams recalls that CBS boss Moonves (for years one of the most powerful people in show business until he resigned in 2018 after being accused of sexual misconduct, allegations he denied) wanted a personal apology from Jackson for embarrassing the network.
She wouldn't do it, but Timberlake showed up at the executive's L.A. office to apologize to Moonves in person and, Abrams says, "basically kiss the ring." He even got "teary-eyed," a CBS communications executive told her.
But these closed-door meetings did nothing to quell the public outrage.
PTC President Tim Winter says that membership went from 750,000 to 1 million in a couple of days following the Super Bowl. Their website also featured a page through which users could submit a complaint directly to the FCC (whose chairman, Michael Powell, called the incident "crass and sophomoric").
Former Sen. Sam Brownback, a Republican from Kansas, reminisces about how that was finally the moment that the American people realized what he'd been "pushing on feverishly in the Congress" regarding the dangers of letting too much racy stuff onto the country's airwaves.
CBS is also the longtime home of the Grammys, on which in 2021 a little ditty called "WAP" was performed, but 17 years ago, Moonves wanted Jackson and Timberlake—if they both wanted to be there and take the stage—to publicly apologize once again.
Ultimately Timberlake performed (twice, neither solo) and Jackson didn't, nor did she attend, but Ron Roecker, former VP of communications and artist relations for The Recording Academy, insists that she was not disinvited, and Jackson's reasons for staying away remained her own. "One can assume," he says.
A clip from the broadcast shows the Wallflowers' Jakob Dylan playfully admonishing the audience to "behave" before announcing Timberlake as the winner of Best Male Pop Vocal Performance for "Cry Me a River."
"Listen, I know it's been a rough week on everybody," the singer, accepting his first-ever Grammy, offered (and got a bit of a laugh from the crowd). "What occurred was unintentional and completely regrettable, and I apologize if you guys were offended."
Still, his dream of winning a Grammy coming true, he also called it "officially the greatest moment of my life."
Needless to say, in addition to the straight-forward criticism, the incident was mocked countless times on late night talk shows, on Saturday Night Live and time and again on red carpets and at award show podiums. Chris Rock worked it into a standup bit that was more about her being too old to show her breast.
The New York Times even calls itself out in Malfunction, highlighting an article that referred to Jackson's "normal middle-aged woman's breast," as the montage of all the focus on why she'd bother to "decorate" her nipple if she didn't plan to show it plays on.
The Times' Wortham says, "It's the biggest indictment of our culture, the idea that a Black woman wouldn't be adorning herself just for herself, that she wouldn't want to be beautiful underneath what she was wearing just for her." (A white male pundit is also shown loudly exclaiming that folks don't gather to watch a football game to see "gangbang rappers grab their privates or Janet Jackson expose a breast," so the Black men onstage didn't entirely escape the racially charged outrage cycle, either.)
Jackson returned to the spotlight on CBS' Late Show With David Letterman, with the host beginning by pointing to the top of her dress and saying, "Now that's almost malfunctioning, isn't it?"
After a few more cracks and a bit of badgering in the name of comedy, Jackson insisted, "Dave, you're gonna make me relive this, I want to put all that behind me."
Jackson's eighth studio album, Damita Jo, still sold more than 3 million copies, but that was considered lackluster in its non-streaming day, especially for her (not helped by MTV staying at arm's length and a diminished radio presence, which a Clear Channel executive insists was not by company-wide design, though he couldn't speak for local stations). After her ninth album, 20 Y.O. (also certified platinum, with 1.5 million copies sold) came out in 2005 and her contract was fulfilled, she departed longtime label Virgin Records for Island Records.
Meanwhile, the FCC was investigating and Congress was holding hearings. "You knew what you were doing!" outraged Republican Rep. Heather Wilson of New Mexico accused then-Viacom President Mel Karmazin. "You knew what kind of entertainment you're selling! And you wanted us all to be abuzz, here in this room and on the playground at my kids' school, because it improves your ratings, it improves your market share and it lines your pockets."
Karmazin, who stepped down in May 2004 and went on to be CEO of Sirius Satellite Radio, repeated that no one at CBS, Viacom, MTV or the NFL had known what was going to transpire at the Super Bowl.
As in, she did it, not us.
Finally Rep. Bobby Rush, a Democrat from Illinois, is seen wondering during these hearings, "Where is Justin Timberlake?" in all this. Rep. Barbara Cubin, Republican from Wyoming, concurred, "Justin Timberlake deserves more than just a slap on the hand. It takes two to tango and I think only a sleazy man would allow Janet Jackson to take the full blame."
Timberlake, sounding more contrite, mused in yet another media interview, "If you consider it 50-50, I mean, I probably got 10 percent of the blame, and I think that says something about society."