djfrosty

With the first quarter of the 21st century coming to a close, Billboard is spending the next few months counting down our staff picks for the 25 greatest pop stars of the last 25 years. We’ve already named our Honorable Mentions and our No. 25, No. 24, No. 23, No. 22, No. 21, No. 20, No. 19, No. 18, No. 17, No. 16 and No. 15 stars, and now we remember the century in Justin Timberlake — a true triple-threat whose insane winning streak to start this century seemed for a while like it might last indefinitely.

Justin Timberlake came into the 21st century as pop’s golden child. From his scene-stealing time as the baby bro of *NSYNC at the turn of the century, to his one-two-three punch of a solo start with the hit-making Justified in 2002, gliding into the cutting-edge FutureSex/LoveSounds in 2006, and rounding out a decade-plus of pop supremacy with the glossy two-part 20/20 Experience in 2013, it began to seem like no amount of time off from music (or even a globally televised Super Bowl catastrophe) could kill his vibe. And while that golden touch has lost a bit of its sheen in the past few years – as Timberlake’s commercially dominant streak tapered to an end – his chokehold on pop culture for those 15 years can’t be overstated.

But Timberlake’s transition from one-fifth of a blockbuster boy band to solo superstardom was never guaranteed. For every Michael Jackson, there are dozens of… well, we won’t name names, but for most boy banders, the group is the beginning and end of their success story. Timberlake was able to be the exception to the pop rule by choosing the exact right time to strike out on his own, and he had the most epic launch pad possible in the turn-of-the-millennium juggernaut that was *NSYNC.

Before we arrive at the year 2000, let’s quickly rewind to 12-year-old Timberlake landing a spot on Disney Channel’s All-New Mickey Mouse Club in 1993, where he met kindred pop spirit JC Chasez (and Britney Spears too, but we’ll get to her later). That was of course well before both were selected by Lou Pearlman as two of the five members of a new boy band, designed to recapture the late ’80s/early ’90s fan frenzy around New Kids on the Block, and backed by earworm productions from Swedish pop maestros, including the soon-to-be-legendary Max Martin. While *NSYNC made a huge impression with their 1997 self-titled debut album – spinning off four Billboard Hot 100-charting hits – their arrival was preceded by Pearlman’s other group, Backstreet Boys, and it felt a bit like the junior group was playing catch-up to their pop peers.

That perception was obliterated when *NSYNC’s new millennium kicked off with the January 2000 release of their first top five Hot 100 hit “Bye Bye Bye,” leading up to March’s No Strings Attached – which marked not just their biggest album debut yet, but the biggest album debut of all time, selling an unprecedented 2.4 million copies in its first week (setting a record that held for 15 years, until Adele’s 25); topping the Billboard 200 for eight weeks; and producing the group’s lone Hot 100 No. 1 in “It’s Gonna Be Me.”

One giant album led to another, with *NSYNC returning the next year with 2001’s Celebrity, their second Billboard 200 No. 1, which saw Timberlake’s introduction as the group’s true star. While Timberlake and Chasez had shared lead vocals on every song to that point, there was a solo showcase on Celebrity that painted the picture of what was to come: “Gone” found JT – who traded his famous ramen-noodle curls for a bad-boy buzzcut – singing every verse (showing off his vocal range, from a gravelly baritone to a floating falsetto) and starring front and center in the black-and-white music video, backed by his groupmates for lush harmonies on the chorus. Another sign of Timberlake’s future: Celebrity’s breakout hit “Girlfriend,” *NSYNC’s first foray into hip-hop-flavored pop and a Hot 100 top five hit, included a guest verse from Nelly and production by The Neptunes, foreshadowing the core sound JT would pursue on his solo debut.

And we can’t paint a picture of just how massive a star Timberlake was at this point without talking about the power couple that catapulted his public profile into another stratosphere. Timberlake started dating Spears, his fellow Mickey Mouse Club alum, in 1999, and their combined pop powers launched a thousand teen-magazine covers (and led to an iconically bizarre dual-denim fever dream of a red-carpet appearance at the 2001 American Music Awards).

The beginning of the end for *NSYNC arrived in April 2002, when the Celebrity Tour, the group’s fourth and (so far) final trek, wrapped up and was followed by an indefinite hiatus. Also in the spring of 2002: Timberlake broke up with Spears – meaning his public identity as both a boy bander and Britney’s boyfriend were behind him as he headed into the summer 2002 creation of his debut solo album, Justified. For the 13-track set, he reunited with The Neptunes on seven cuts and connected with hip-hop heavyweight Timbaland for the first time on four songs. Just four months after pressing pause on *NSYNC, JT’s debut solo single, the Neptunes-produced “Like I Love You,” arrived in September 2002, followed by the Nov. 5 release of the full album. 

“Like I Love You” peaked just outside the Hot 100 top 10, and Justified debuted and peaked at No. 2 on the Billboard 200 – but the heat around Timberlake’s budding solo stardom had just started boiling. The Timbaland-produced “Cry Me a River” came next, climbing all the way to No. 3 on the Hot 100 by memorably mining the Britney breakup, fueling cheating rumors and deploying a Spears doppelganger in its eyebrow-raising music video. JT scored two more top 40 Hot 100 hits with a final pair of singles from the album: the MJ-indebted “Rock Your Body” (No. 5) and the Pharrell-intro’d “Señorita” (No. 27). Aside from his chart success, Timberlake also managed something on his debut album that *NSYNC never accomplished, picking up his first two career Grammys at the 2004 ceremony: best pop vocal album for Justified and best male pop vocal performance for “Cry Me a River,” from five nominations.

After Justified, Timberlake was hot enough to get the call to appear onstage with headliner Janet Jackson at the 2004 Super Bowl halftime show. What should have been a victory lap for the newly minted solo star turned into a world-famous nightmare when Timberlake accidentally exposed Jackson’s breast in front of 140 million TV viewers (just as he sang the “Rock Your Body” lyric “better have you naked by the end of this song”), later coining the infamous phrase “wardrobe malfunction” in his apology. But while Jackson’s career famously suffered in the aftermath, JT was largely left strikingly unaffected.

After back-to-back releases from *NSYNC followed quickly by his solo debut, fans had to wait a grueling four years for Timberlake’s next album. Led by “SexyBack” — his most experimental single yet, with a harsh but intoxicating electro-funk sound — FutureSex/LoveSounds debuted atop the Billboard 200 in September 2006 and signaled his arrival as a fully formed adult pop star. He leaned into his Timbaland partnership on the project, scoring his first three solo Hot 100 No. 1s with the album’s first three singles: “SexyBack”; the percussive T.I.-featuring ballad “My Love” and the two-part “What Goes Around…Comes Around,” basically a karmic sequel to “Cry Me a River.” He picked up another four Grammys across the ‘07 and ‘08 ceremonies for the project, cementing his spot as both a critical and commercial heavyweight. He also sprinkled his pop magic onto other artists’ singles in his downtime, returning the favor to Timbaland with the Hot 100-topping “Give It to Me” (also alongside Nelly Furtado) and gracing a trio of top five hits in Madonna’s “4 Minutes,” T.I.’s “Dead and Gone” and 50 Cent’s “Ayo Technology.”

By this point, Timberlake had introduced a new layer to his many talents by hosting Saturday Night Live during both of his solo album cycles (he’d eventually join the Five-Timers Club in 2013) and introducing his recurring sketch “The Barry Gibb Talk Show” with Jimmy Fallon during his debut 2003 hosting gig. But the real gift came in December 2006, when Timberlake co-starred in The Lonely Island digital short “D–k in a Box,” which went on to win an Emmy for outstanding original music and lyrics the next year and virtually invented the idea of a viral hit on YouTube, the video-sharing site that had debuted only a year prior.

That SNL success seemed to feed into Timberlake’s next move, as he took a nearly seven-year break from music to pour himself into an acting career, with varying degrees of success (there was Oscar-favorite The Social Network and charming Mila Kunis rom-com Friends With Benefits, but there was also The Love Guru). At this point, it was unclear whether Timberlake would ever return to his recording career, but it was a testament to the level of stardom he’d reached that his fans never stopped anticipating his musical return, no matter how long he stayed on the sidelines.

He eventually found his way back to music, taking on a natty Rat Pack-inspired persona in a tuxedo and slick new hairstyle as he rolled out the smooth Jay-Z-featuring “Suit & Tie” (No. 3 peak on the Hot 100) in January 2013 and the eight-minute ode to wife Jessica Biel “Mirrors” (No. 2) in February ahead of the March release of The 20/20 Experience. The breathless excitement for Timberlake’s crooning comeback was made clear when 20/20 sold 968,000 copies in its first week – the largest solo week ever for JT – and finished as the year-end No. 1 Billboard 200 album for 2013. While the project was generally embraced by fans and critics alike, there were a few misgivings this time – including some hand-wringing over the songs’ excessive runtimes – compared to the flawless approval rating of its FutureSex/LoveSounds predecessor. 

The long-awaited album wasn’t the only music JT had up his tux sleeve that year: Timberlake surprised fans by announcing an imminent Part 2 coming for The 20/20 Experience – and it arrived just months later, scoring him a pair of Billboard 200 chart-toppers in 2013. The project was preceded by what might be considered Timberlake’s first musical misstep: Lead single “Take Back the Night” shared a name with a sexual-assault awareness group, but its suggestive lyrics instead told the story of a carefree, sexy night. JT apologized (“neither my song nor its lyrics have any association with the organization”) and shed light on the group’s efforts (“something we all should rally around”), but the song never really rose above the controversy, topping out at No. 29 on the Hot 100. There were two success stories from 2 of 2, however: The dreamy ballad “Not a Bad Thing” climbed all the way to the Hot 100’s top 10 eight months after the album’s release, and the twangy “Drink You Away” became JT’s first song to reach Billboard’s Country Airplay chart, following a lauded team-up with Chris Stapleton at the 2015 CMA Awards.

After sticking to his electro-pop sound on top 10 lead single “Filthy,” Timberlake found another country moment on his February 2018 album Man of the Woods when he re-teamed with Stapleton for the strummy standout cut “Say Something” and scored another Hot 100 top 10. Days after the release of his fifth studio album – which debuted atop the Billboard 200, but with a much smaller first week than 20/20 — Timberlake returned to the Super Bowl stage, 14 years after the Janet incident, for a much less incendiary showing and headlining for the first time. 

As JT made a memorable meme out of #SelfieKid in the Minneapolis crowd and paid tribute to hometown hero Prince at Super Bowl LII, some fans questioned why Timberlake was invited back to the Super Bowl when Jackson never was, and the pop star directly addressed that criticism years later in a 2021 Instagram statement. His comments were prompted by the February 2021 release of the documentary Framing Britney Spears, which put his post-breakup behavior in a new light and led to renewed criticism over the double-standard at play following the Super Bowl controversy, and Timberlake’s failure to properly support Jackson over the blowback she’d faced at the time, which he’d since expressed regret over. “I specifically want to apologize to Britney Spears and Janet Jackson both individually because I care for and respect these women and I know I failed,” he wrote in part.

While he had amassed his fair share of detractors by this point, Timberlake had also broken through to a new, much younger generation of fans by combining his Hollywood aspirations with his musical prowess and voicing Branch in the pop-music-obsessed Trolls animated movie series, scoring his fifth Hot 100 No. 1 along the way with the bouncy, Oscar-nominated 2016 soundtrack single “Can’t Stop the Feeling!” Timberlake brought things full-circle in 2023 for Trolls Band Together, when he reunited his *NSYNC bandmates in the movie and for their first new song in 21 years, the whistling confection “Better Place.” 

And that wasn’t all he had in store for fans who had been with him from the beginning: For his sixth studio album Everything I Thought It Was (led by top 20 single “Selfish”), the pop quintet got together yet again for “Paradise,” which they live-debuted just before the album’s March 15 release, and which seemed to speak directly to the fans who had been begging the boy band to reunite for decades (sample lyric: “I’ve been waiting forever/ Right here for this moment”). 

Aside from the *NSYNC reunion, JT’s latest album mostly underwhelmed, debuting at No. 4 on the Billboard 200 and failing to produce any lasting hits. That lackluster performance was further compounded when Timberlake’s summer DWI arrest in The Hamptons amid the Forget Tomorrow World Tour became an online punchline, thanks to his police-reported prediction of “This is going to ruin the tour… the world tour.” But it didn’t: In fact, the recently extended trek is on track to land in the top 10 of Billboard’s year-end tours list. And the hunger for a potential *NSYNC reunion tour is still raging as well: “Bye Bye Bye” even recharted on the Hot 100 this year – 24 years after its initial Hot 100 debut – off its use on the Deadpool & Wolverine soundtrack. 

It seems fitting that Timberlake would find himself approaching the quarter-century mark by (however briefly) returning to the turn-of-the-century group responsible for much of what he’s created so far in his career. After all, while he’s surely picked up fans along the way who weren’t around for his *NSYNC heyday – whether they were too old to be invested in a boy band or too young to understand (or not even alive for it, for that matter) – the bond formed from watching someone at age 12 on Disney Channel to following along on their boy-band journey to seeing their ascension to the top of the pop pyramid is impossible to replicate. There’s an unconditional love that comes from those day 1 fans that has unquestionably fueled JT’s nearly three decades in pop, through its highs and lows. In the end, ain’t nobody love him like we love him.

Read more about the Greatest Pop Stars of the 21st Century here — and be sure to check back on Tuesday when our No. 13 artist is revealed!