Best Pop Singers of 21st Century (No. 14)

With the primary quarter of the twenty first century coming to a detailed, Billboard is spending the following few months counting down our workers picks for the 25 biggest pop stars of the final 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 bear in mind the century in Justin Timberlake — a real triple-threat whose insane profitable streak to begin this century appeared for some time prefer it would possibly final indefinitely.

Justin Timberlake got here into the twenty first century as pop’s golden baby. From his scene-stealing time because the child bro of *NSYNC on the flip of the century, to his one-two-three punch of a solo begin 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 shiny two-part 20/20 Expertise in 2013, it started to appear like no period of time off from music (or perhaps a globally televised Tremendous Bowl catastrophe) may kill his vibe. And whereas that golden contact has misplaced a little bit of its sheen up to now few years – as Timberlake’s commercially dominant streak tapered to an finish – his chokehold on popular culture for these 15 years can’t be overstated.

However Timberlake’s transition from one-fifth of a blockbuster boy band to solo superstardom was by no means assured. For each Michael Jackson, there are dozens of… properly, we received’t identify names, however for many boy banders, the group is the start and finish of their success story. Timberlake was capable of be the exception to the pop rule by selecting the precise proper time to strike out on his personal, and he had probably the most epic launch pad attainable within the turn-of-the-millennium juggernaut that was *NSYNC.

Earlier than we arrive on the yr 2000, let’s shortly rewind to 12-year-old Timberlake touchdown a spot on Disney Channel’s All-New Mickey Mouse Membership in 1993, the place he met kindred pop spirit JC Chasez (and Britney Spears too, however we’ll get to her later). That was after all properly earlier than each had been chosen by Lou Pearlman as two of the 5 members of a brand new boy band, designed to recapture the late ’80s/early ’90s fan frenzy round New Youngsters on the Block, and backed by earworm productions from Swedish pop maestros, together with the soon-to-be-legendary Max Martin. Whereas *NSYNC made an enormous impression with their 1997 self-titled debut album – spinning off 4 Billboard Sizzling 100-charting hits – their arrival was preceded by Pearlman’s different group, Backstreet Boys, and it felt a bit just like the junior group was enjoying catch-up to their pop friends.

That notion was obliterated when *NSYNC’s new millennium kicked off with the January 2000 launch of the highest 5 Sizzling 100 hit “Bye Bye Bye,” main as much as March’s No Strings Connected – which marked not simply their largest album debut but, however the largest album debut of all time, promoting an unprecedented 2.4 million copies in its first week (setting a file that held for 15 years, till Adele’s 25); topping the Billboard 200 for eight weeks; and producing the group’s lone Sizzling 100 No. 1 in “It’s Gonna Be Me.”

One big album led to a different, with *NSYNC returning the following yr with 2001’s Celeb, their second Billboard 200 No. 1, which noticed Timberlake’s introduction because the group’s true star. Whereas Timberlake and Chasez had shared lead vocals on each tune to that time, there was a solo showcase on Celeb that painted the image of what was to return: “Gone” discovered JT – who traded his well-known ramen-noodle curls for a bad-boy buzzcut – singing each verse (exhibiting off his vocal vary, from a gravelly baritone to a floating falsetto) and starring entrance and heart within the black-and-white music video, backed by his groupmates for lush harmonies on the refrain. One other signal of Timberlake’s future: Celeb’s breakout hit “Girlfriend,” *NSYNC’s first foray into hip-hop-flavored pop and a Sizzling 100 prime 5 hit, included a visitor verse from Nelly and manufacturing by The Neptunes, foreshadowing the core sound JT would pursue on his solo debut.

And we are able to’t paint an image of simply how large a star Timberlake was at this level with out speaking in regards to the energy couple that catapulted his public profile into one other stratosphere. Timberlake began courting Spears, his fellow Mickey Mouse Membership alum, in 1999, and their mixed pop powers launched a thousand teen-magazine covers (and led to an iconically weird dual-denim fever dream of a red-carpet look on the 2001 American Music Awards).

The start of the tip for *NSYNC arrived in April 2002, when the Celeb Tour, the group’s fourth and (to this point) remaining trek, wrapped up and was adopted by an indefinite hiatus. Additionally within the spring of 2002: Timberlake broke up with Spears – that means his public identification as each a boy bander and Britney’s boyfriend had been behind him as he headed into the summer season 2002 creation of his debut solo album, Justified. For the 13-track set, he reunited with The Neptunes on seven cuts and linked with hip-hop heavyweight Timbaland for the primary time on 4 songs. Simply 4 months after urgent pause on *NSYNC, JT’s debut solo single, the Neptunes-produced “Like I Love You,” arrived in September 2002, adopted by the Nov. 5 launch of the complete album. 

“Like I Love You” peaked simply outdoors the Sizzling 100 prime 10, and Justified debuted and peaked at No. 2 on the Billboard 200 – however the warmth round Timberlake’s budding solo stardom had simply began boiling. The Timbaland-produced “Cry Me a River” got here subsequent, climbing all the way in which to No. 3 on the Sizzling 100 by memorably mining the Britney breakup, fueling dishonest rumors and deploying a Spears doppelganger in its eyebrow-raising music video. JT scored two extra prime 40 Sizzling 100 hits with a remaining pair of singles from the album: the MJ-indebted “Rock Your Physique” (No. 5) and the Pharrell-intro’d “Señorita” (No. 27). Except for his chart success, Timberlake additionally managed one thing on his debut album that *NSYNC by no means completed, selecting up his first two profession Grammys on the 2004 ceremony: finest pop vocal album for Justified and finest male pop vocal efficiency for “Cry Me a River,” from 5 nominations.

After Justified, Timberlake was scorching sufficient to get the decision to seem onstage with headliner Janet Jackson on the 2004 Tremendous Bowl halftime present. What ought to have been a victory lap for the newly minted solo star was a world-famous nightmare when Timberlake by accident uncovered Jackson’s breast in entrance of 140 million TV viewers (simply as he sang the “Rock Your Physique” lyric “higher have you ever bare by the tip of this tune”), later coining the notorious phrase “wardrobe malfunction” in his apology. However whereas Jackson’s profession famously suffered within the aftermath, JT was largely left strikingly unaffected.

After back-to-back releases from *NSYNC adopted shortly by his solo debut, followers needed to wait a grueling 4 years for Timberlake’s subsequent album. Led by “SexyBack” — his most experimental single but, with a harsh however intoxicating electro-funk sound — FutureSex/LoveSounds debuted atop the Billboard 200 in September 2006 and signaled his arrival as a totally shaped grownup pop star. He leaned into his Timbaland partnership on the undertaking, scoring his first three solo Sizzling 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 Round…Comes Round,” mainly a karmic sequel to “Cry Me a River.” He picked up one other 4 Grammys throughout the ‘07 and ‘08 ceremonies for the undertaking, cementing his spot as each a crucial and business heavyweight. He additionally sprinkled his pop magic onto different artists’ singles in his downtime, returning the favor to Timbaland with the Sizzling 100-topping “Give It to Me” (additionally alongside Nelly Furtado) and gracing a trio of prime 5 hits in Madonna’s “4 Minutes,” T.I.’s “Lifeless and Gone” and 50 Cent’s “Ayo Know-how.”

By this level, Timberlake had launched a brand new layer to his many skills by internet hosting Saturday Night time Stay throughout each of his solo album cycles (he’d finally be part of the 5-Timers Membership in 2013) and introducing his recurring sketch “The Barry Gibb Discuss Present” with Jimmy Fallon throughout his debut 2003 internet hosting gig. However the actual present got here in December 2006, when Timberlake co-starred in The Lonely Island digital quick “D–ok in a Field,” which went on to win an Emmy for excellent authentic music and lyrics the following yr — one among 4 Emmys he’s received for his work on the present — and nearly invented the thought of a viral hit on YouTube, the video-sharing web site that had debuted solely a yr prior.

That SNL success appeared to feed into Timberlake’s subsequent transfer, as he took a virtually seven-year break from music to pour himself into an performing profession, with various levels of success (there was Oscar-favorite The Social Community and charming Mila Kunis rom-com Buddies With Advantages, however there was additionally The Love Guru). At this level, it was unclear whether or not Timberlake would ever return to his recording profession, nevertheless it was a testomony to the extent of stardom he’d reached that his followers by no means stopped anticipating his musical return, irrespective of how lengthy he stayed on the sidelines.

He finally discovered his method again to music, taking up a natty Rat Pack-inspired persona in a tuxedo and slick new coiffure as he rolled out the sleek Jay-Z-featuring “Go well with & Tie” (No. 3 peak on the Sizzling 100) in January 2013 and the eight-minute ode to spouse Jessica Biel “Mirrors” (No. 2) in February forward of the March launch of The 20/20 Expertise. The breathless pleasure for Timberlake’s crooning comeback was made clear when 20/20 bought 968,000 copies in its first week – the biggest solo week ever for JT – and completed because the year-end No. 1 Billboard 200 album for 2013. Whereas the undertaking was usually embraced by followers and critics alike, there have been a couple of misgivings this time – together with some hand-wringing over the songs’ extreme runtimes – in comparison with the flawless approval score of its FutureSex/LoveSounds predecessor. 

The long-awaited album wasn’t the one music JT had up his tux sleeve that yr: Timberlake shocked followers by asserting an imminent Half 2 coming for The 20/20 Expertise – and it arrived simply months later, scoring him a pair of Billboard 200 chart-toppers in 2013. The undertaking was preceded by what may be thought-about Timberlake’s first musical misstep: Lead single “Take Again the Night time” shared a reputation with a sexual-assault consciousness group, however its suggestive lyrics as an alternative advised the story of a carefree, horny night time. JT apologized (“neither my tune nor its lyrics have any affiliation with the group”) and make clear the group’s efforts (“one thing all of us ought to rally round”), however the tune by no means actually rose above the controversy, topping out at No. 29 on the Sizzling 100. There have been two success tales from 2 of two, nonetheless: The dreamy ballad “Not a Unhealthy Factor” climbed all the way in which to the Sizzling 100’s prime 10 eight months after the album’s launch, and the twangy “Drink You Away” grew to become JT’s first tune to achieve Billboard’s Nation Airplay chart, following a lauded team-up with Chris Stapleton on the 2015 CMA Awards.

After sticking to his electro-pop sound on prime 10 lead single “Filthy,” Timberlake discovered one other nation second on his February 2018 album Man of the Woods when he re-teamed with Stapleton for the strummy standout lower “Say One thing” and scored one other Sizzling 100 prime 10. Days after the discharge of his fifth studio album – which debuted atop the Billboard 200, however with a a lot smaller first week than 20/20 — Timberlake returned to the Tremendous Bowl stage, 14 years after the Janet incident, for a a lot much less incendiary exhibiting and headlining for the primary time. 

As JT made a memorable meme out of #SelfieKid within the Minneapolis crowd and paid tribute to hometown hero Prince at Tremendous Bowl LII, some followers questioned why Timberlake was invited again to the Tremendous Bowl when Jackson by no means was, and the pop star immediately addressed that criticism years later in a 2021 Instagram assertion. His feedback had been prompted by the February 2021 launch of the documentary Framing Britney Spears, which put his post-breakup habits in a brand new mild and led to renewed criticism over the double-standard at play following the Tremendous Bowl controversy, and Timberlake’s failure to correctly assist Jackson over the blowback she’d confronted on the time, which he’d since expressed remorse over. “I particularly need to apologize to Britney Spears and Janet Jackson each individually as a result of I look after and respect these ladies and I do know I failed,” he wrote partially.

Whereas he had amassed his fair proportion of detractors by this level, Timberlake had additionally damaged by to a brand new, a lot youthful technology of followers by combining his Hollywood aspirations together with his musical prowess and voicing Department within the pop-music-obsessed Trolls animated film sequence, scoring his fifth Sizzling 100 No. 1 alongside the way in which with the bouncy, Oscar-nominated 2016 soundtrack single “Can’t Cease the Feeling!” Timberlake introduced issues full-circle in 2023 for Trolls Band Collectively, when he reunited his *NSYNC bandmates within the film and for his or her first new tune in 21 years, the whistling confection “Higher Place.” 

And that wasn’t all he had in retailer for followers who had been with him from the start: For his sixth studio album Every part I Thought It Was (led by prime 20 single “Egocentric”), the pop quintet acquired collectively but once more for “Paradise,” which they live-debuted simply earlier than the album’s March 15 launch, and which appeared to talk on to the followers who had been begging the boy band to reunite for many years (pattern lyric: “I’ve been ready eternally/ Proper right here for this second”). 

Except for the *NSYNC reunion, JT’s newest album largely underwhelmed, debuting at No. 4 on the Billboard 200 and failing to supply any lasting hits. That lackluster efficiency was additional compounded when Timberlake’s summer season DWI arrest in The Hamptons amid the Overlook Tomorrow World Tour grew to become a web-based punchline, because of his police-reported prediction of “That is going to destroy the tour… the world tour.” However it didn’t: The truth is, the not too long ago prolonged trek is on monitor to land within the prime 10 of Billboard’s year-end excursions checklist. And the starvation for a possible *NSYNC reunion tour continues to be raging as properly: “Bye Bye Bye” even recharted on the Sizzling 100 this yr – 24 years after its preliminary Sizzling 100 debut – off its use on the Deadpool & Wolverine soundtrack. 

It appears becoming that Timberlake would discover himself approaching the quarter-century mark by (nonetheless briefly) returning to the turn-of-the-century group accountable for a lot of what he’s created to this point in his profession. In spite of everything, whereas he’s certainly picked up followers alongside the way in which who weren’t round for his *NSYNC heyday – whether or not they had been too previous to be invested in a boy band or too younger to know (or not even alive for it, for that matter) – the bond shaped from watching somebody at age 12 on Disney Channel to following alongside on their boy-band journey to seeing their ascension to the highest of the pop pyramid is not possible to copy. There’s an unconditional love that comes from these day 1 followers that has unquestionably fueled JT’s almost three a long time in pop, by its highs and lows. In the long run, ain’t no person love him like we love him.

Learn extra in regards to the Best Pop Stars of the twenty first Century right here — and remember to test again on Tuesday when our No. 13 artist is revealed!