What better way to ring in the new year than Janet Jackson live in Las Vegas? Teasing her 2023 Together Again Tour, Jackson entertained a party-hearty Sin City audience with a deep catalog of songs older than many of the revelers in attendance.

The Wynn Las Vegas came alive with “What Have You Done for Me Lately,” “Love Will Never Do (Without You),” “That’s the Way Love Goes,” “Got ’Til It’s Gone” and more than 20 other surefire chart-toppers from the queen of Black American pop. Judging by the boozy singalong in the wee hours, fans of multiple generations know every last word of her biggest hits.

Dressed in signature Rhythm Nation-era black with chunky combat boots and flanked by four male dancers, Jackson commanded the stage like she’d never left it. At 56, with a celebrated discography 11 studio albums deep, she refuses to let her legacy lie fallow.

Jackson has earned the status of a Diana Ross or a Tina Turner, that of a legend in her own time. Still, her road to becoming a superstar elder stateswoman differs from theirs in one peculiar way.

The “wardrobe malfunction” of 2004’s Super Bowl XXXVIII—when Justin Timberlake inadvertently bared Jackson’s pierced right nipple to 150 million viewers for 9/16ths of a second—has arguably affected the chart success and sales of her work ever since.

Having largely parted ways with longtime collaborators Jimmy Jam and Terry Lewis, responsible for slam-dunk multiplatinum classics like Control (1986), Janet Jackson’s Rhythm Nation 1814 (1989), janet. (1993) and The Velvet Rope (1997), to record with celebrated producers like Jermaine Dupri, Rodney Jerkins, Dallas Austin and Kanye West, she thereafter embarked on what remains an unsung period of her career. In recognition of Jackson’s role as an American icon, a reassessment of this work is overdue.

Damita Jo

“I honestly don’t believe she was blacklisted,” says Dupri. “I just felt like enough of the people who were bosses of different corporations and the label, they just didn’t speak up. Now, you got Megan Thee Stallion onstage twerking during the Grammy Awards, the cameraman basically in her crotch the whole time. And that’s cool to see at home, right?”

Contrary to what Dupri surmises, after the Super Bowl, Viacom CEO Les Moonves reportedly banned the broadcast of Jackson’s music and videos from MTV, VH1 and Infinity Broadcasting, which operated more than 180 radio stations nationwide, triggering a snowball effect.

Cast in an ABC biopic of Lena Horne, Jackson was reportedly forced to withdraw. Invitations to perform on the 2004 Grammy Awards (which aired a week after the Super Bowl) and MTV Video Music Awards were both rescinded.

“I was president of NARAS here in Atlanta and I quit,” Dupri remembers. “Because how am I the president of an organization that’s telling my [artist] she can’t come to do the show? That don’t look right. So, I quit. I took that stance because this is what I feel like other people should be doing if you fuck with the person and you don’t fuck with what’s happening.”

Damita Jo, Janet’s eighth studio album, released the month after the halftime show heard ’round the world, was her first to drop after the incident. It sold 3 million unitsâ€•this from a global superstar whose Rhythm Nation had moved north of 12 million, with a record-breaking seven Top 5 singles. Fans still debate how the album and its follow-ups would’ve fared without the intercession of “Nipplegate” and what else might have contributed to her subsequent downward commercial trajectory. The question, of course, is well-nigh impossible to answer.

Damita Jo earned two Grammy nominations, for Best Contemporary R&B Album and Best Female R&B Vocal Performance for “I Want You,” and “I Want You” was ultimately certified platinum. But the set’s relative absence on the airwaves in 2004, along with dismal chart positions, lent it an air of failure. In fact, Damita Jo sold more than five million fewer copies than Jackson’s previous long-player, 2001’s All for You.

For only the second time since entering into a longtime musical partnership with Jam and Lewis, on the career-defining Control, she’d invited other producers to play a lead role. Kanye West, fresh off his debut, The College Dropout, assisted on “Strawberry Bounce” and second single “I Want You” and made a guest appearance on “My Baby.” Babyface laid down his one-and-only Janet production with “Thinkin’ Bout My Ex.” Dallas Austin lent Damita Jo “Sexhibition” and lead single “Just a Little While.” Rap producer Scott Storch (“Island Life”) and Swedish songwriters Bag & Arnthor (“All Nite [Don’t Stop],” “SloLove”) also represented.

Virgin Records serviced three singles from Damita Jo: “Just a Little While,” “I Want You” and “All Nite (Don’t Stop).” The first of these had been leaked and begun to gather steam. But that momentum stalled after the Super Bowl. “Just a Little While” peaked at #45 on the Pop chart, her worst showing for a single since “Come Give Your Love to Me,” from her self-titled debut back in 1982. The Motown-esque love song “I Want You”—co-written by newbie songwriter John Legend—failed to rise above #57. “All Nite (Don’t Stop),” one of the most electrifying dance tracks of Jackson’s career, at least, broke into the Top 40, reaching #33.

So how does Damita Jo sound 19 years later?

The album is an exploration of love and intimacy from different sides of Jackson’s psyche. She was born Janet Damita Jo Jackson, and Damita Jo was conceived as an aggressive alter-ego—not unlike Eminem’s Slim Shady or Beyoncé’s Sasha Fierce. This was Strawberry of “Strawberry Bounce,” who urged listeners to “lose control.”

“A songwriter is like a novelist,” Jackson told biographer David Ritz in a 2004 Upscale story. “You invent characters… I hope Strawberry is a good character. Sexually, she’s on fire. She doesn’t mince words. She has to have it and doesn’t care who knows it. As a writer, I created her. As a singer, I live through her. As an artist, I find her compelling. She might be crazyâ€•she might even be twistedâ€•but her sexual adventures are exciting. I want her music to reflect that excitement.”

This overt sexuality of Damita Jo feels a little strained. “Warmth,” a balladic ode to fellatio co-produced by Rockwilder, is paired with “Moist,” a similarly delicate paean to cunnilingus. Jackson offers metaphors about overflowing oceans, pouring rain and waves of passion.

Indeed, critics charged that she ran a voracious sexuality into the ground on songs like “Sexhibition.” Her evolution from the chaste stance of Control’s “Let’s Wait Awhile” to Rhythm Nation’s “Someday Is Tonight” to the erotic coming-out of janet. seemed a natural progression. But the strip-club titillation of “Strawberry Bounce,” the aforementioned oral-sex tandem and other such moments make one wonder if Janet was trying to co-opt Madonna’s schtickâ€•at what turned out to be exactly the wrong moment.

“Moist” nonetheless qualifies as an underrated classic. So does “All Nite (Don’t Stop),” which managed to sufficiently surmount the media hatchet job to top the Dance chart. A house jam in the mold of janet.’s “Throb,” this energetic Bag & Arnthor production also traveled up the singles chart when Jackson released Discipline four years later.

The “All Nite” video, meanwhile, showcased a squad of back-up dancers rehearsing in L.A.’s abandoned El Dorado Hotel amid a blackout. The choreography is some of the best ever seen in a Janet Jackson video (which is saying something).

As the tentpoles of Jackson’s oeuvre are dance tracks and slow jams, it’s perhaps not surprising that “Moist” and “All Nite,” in particular, did Damita Jo right.

20 Y.O.

Of the 25 songs Jackson performed on New Year’s Eve, only one, “R&B Junkie,” came from Damita Jo. Follow-up 20 Y.O. (2006) wasn’t represented at all.

20 Y.O. commemorated the 20th anniversary of Control, which had changed everything for Jackson. Full of hit singles that, one by one, “crossed over” from R&B to pop—“What Have You Done for Me Lately,” “Nasty,” “Control,” “When I Think of You,” “Let’s Wait Awhile”—Control signaled her emancipation from the bubblegum soul of her first two albums as she stepped into her own power at age 20. Hence “20 Y.O.,” a title suggested by Dupri (Destiny’s Child, Mariah Carey, Usher), who produced seven of the album’s tracks.

“I feel like a lot of times Black artists lose that space in their mind and don’t understand: If your base is not fucking with you, you’re finished,” says Dupri. “That’s just how I make music; I make music based on your base. And I feel like with that whole album, what I tapped back into was Janet’s pure, core base.”

The focus was meant to be on the dancefloor, a reprise of the Control ethos. Productions by Dr. Dre, West, Kwamé, The Trak Starz and The Neptunes were ultimately scrapped in favor of Dupri’s steering the album back to Janet’s roots.

20 Y.O. entered the Black albums chart at the top on the strength of 1.5 million copies sold. Its lead single, the midtempo ballad “Call on Me,” featuring guest vocals by Nelly, hit #1 on the Black singles chart. Jackson saw 20 Y.O.’s singles flounder on the Pop chart, however, and promoting the album was like fighting with one arm tied behind her back. “Call on Me” peaked at #25 on the pop singles chart. Director Hype Williams had overseen one of the most expensive videos of all time—with a budget in excess of $1 million—for it, but MTV wouldn’t air it.

20 Y.O. debuted at #2 on the pop albums chart, but sales dropped by more than 74% its second week. The lively second single, “So Excited,” petered out at #90. The Quiet Storm-ready “With U,” a thematic sequel to Control’s “Let’s Wait Awhile,” never cracked the Pop chart at all.

In the end, 20 Y.O. was nominated for the Grammy for Best Contemporary R&B Album and moved a relatively scant million copies.

In part 2: Discipline, Unbreakable and more