From the moment Justin Timberlake first stepped into the spotlight at just 11 years old, his star power was strikingly apparent. Initially dabbling in country music on Star Search, he further displayed his knack for performing on The Mickey Mouse Club in 1993 and 1994 before being recruited for the boy band *NSYNC in 1995 — and soon, he was on his way to pop domination.
As the group's popularity soared and they sold over 70 million records worldwide, so did Timberlake's solo appeal. With his curly blond hair and falsetto that would make Michael Jackson proud, he became a defining figure in the late '90s/early 2000s zeitgeist. He took the lead in several *NSYNC songs and progressively developed his songwriting skills, hinting to the world that he was a star of his own right.
By the time <em>NSYNC halted in early 2002, Timberlake's solo career was not a mere possibility, but an undeniable next step. A few months later, he released his debut album, Justified*, which set the stage for one of the most innovative, defining artists of his time. In the two decades since, Timberlake has released five studio albums (with a sixth reportedly on the way), sold more than 88 million records, collaborated with the likes of Jay-Z and Madonna, and won 10 GRAMMYs. It's hard to imagine pop music today without his contributions.
Although Timberlake has periodically taken some time off music to focus on his family, acting and producing, a comeback was always around the corner. Last week, for example, he reunited with *NSYNC at the 2023 MTV Video Music Awards and confirmed the release of their first new song in 20 years, "Better Place," out Sept. 29.
He also recently reunited with Nelly Furtado and Timbaland for "Keep Going Up," the long-awaited follow-up to their 2007 smash "Give It To Me." Timbaland — a longtime collaborator of Timberlake's — further teased what's to come for JT, telling Variety that Timberlake's next album is "finished up" and sounds like "FutureSex/LoveSounds part two."
To celebrate these upcoming chapters, as well as Timberlake's boundless creativity, GRAMMY.com looks back at the most defining songs in his trailblazing career.
"Pop," Celebrity (2001)
A response to all the animosity surrounding the success of late 90s' boy bands, "Pop" gave us *NSYNC at their most "no strings attached." Composed by Timberlake in partnership with choreographer, director, and songwriter Wade Robson, it blended electropop, metal riffs and Timberlake's signature beatboxing into a thrilling, limitless portrait of what being a pop star really means.
"It doesn't matter/ 'Bout the clothes I wear, and where I go, and why/ All that matters/ Is that you get hyped, and we'll do it to you every time," Timberlake sings in the pre-chorus. As the first single off <em>NSYNC's last album, 2001's Celebrity*, "Pop" foreshadowed key elements of Timberlake's burgeoning success — setting sights on his impending, hit-filled solo career.
"Gone," Celebrity (2001)
Another collaboration between Timberlake and Robson for Celebrity, "Gone" remains one of the most stirring ballads of the new millennium. Originally written for Michael Jackson, who passed on the offer — but later regretted it, as Timberlake told Oprah's Master Class Podcast in 2014 — "Gone" was the first and only *NSYNC single where Timberlake sings all the lead vocals and plays the music video protagonist.
Although its success led to a nomination for Best Pop Performance by a Duo or Group with Vocals at the 2002's GRAMMY Awards, the song unveiled uncomfortable feelings about the future of the group. If *NSYNC were to halt activities, it laid bare the fact that Timberlake could survive — and thrive — as a soloist just as well.
"Like I Love You," Justified (2002)
As many suspected, <em>NSYNC did go into a hiatus after the release of Celebrity, and Timberlake's much-anticipated solo debut came shortly after. In November 2002, he released the studio album Justified*, spearheaded by lead single "Like I Love You."
Pairing his penmanship with producer duo the Neptunes, Timberlake found an exquisite recipe to express himself. "Like I Love You" posed a sleek introduction to a fully-developed star, mixing funk drums, pop beats, Spanish guitars, sultry falsettos, and a participation by hip-hop duo Clipse. Coincidentally landing the same spot on the Billboard Hot 100 as "Gone" at No. 11, "Like I Love You" showed that Timberlake was able — and ready — to hold his own.
"Cry Me a River," Justified (2002)
If "Like I Love You" was an introduction to Justin Timberlake the soloist, follow-up single "Cry Me a River" cemented him as 2002's main character. A vengeful opera inspired by his former (and very high-profile) relationship with Britney Spears, Timberlake showed his spiteful side — one that would later resurface on his second album, FutureSex/LoveSounds.
The poignancy of his feelings is aided by producers Timbaland and Scott Storch, who crafted a haunting synthscape filled with wails and warnings. In the music video, Timberlake finally sheds his good-boy image, breaking into a Spears look-alike's mansion to film steamy moments of himself with another woman.
On top of giving the audience much to think about, "Cry Me a River" gave Timberlake one his first two solo GRAMMY Awards in 2003: the song won Best Male Pop Vocal Performance, and Justified won Best Pop Vocal Album.
"Señorita," Justified (2002)
Justified offered hit after hit, and although "Señorita" wasn't the biggest (it peaked at No. 27 on the Hot 100), it's still a Timberlake staple. The song highlighted Timberlake's commitment to go beyond expectations, as he created his own deconstructed salsa, pushing and pulling vocals around the Neptunes' unmistakable drum beats and Stevie Wonder influences.
While singles like "Rock Your Body" may have found more popularity, "Señorita" and its odd little strutting intro is instantly recognizable — and remains one of Timberlake's best displays of the fun he has in the studio . The call-and-response section at the end, where Timberlake directs "the fellas and the ladies" to sing in different vocal tones, is the cherry on top of it all.
"SexyBack," FutureSex/LoveSounds (2006)
Four years after Justified, Timberlake returned raunchier than ever: "I'm bringing sexy back," he sings in the opening line of "SexyBack," unknowingly birthing 2006's ultimate catchphrase. The first single off his highly-acclaimed sophomore album, FutureSex/LoveSounds, "SexyBack" became Timberlake's first No.1 song on the Billboard Hot 100, and further solidified the finesse of his collaborations with Timbaland.
Scurrying through a suffocating dance floor, "SexyBack" distorts everything it touches, creating a cybernetic atmosphere where Timberlake will both "let you whip me, if I misbehave" and make you "watch how I attack." Timbaland's low vocals bounce off Timberlake's high-pitched lines and make for a breathless, sweaty run.
"My Love," FutureSex/LoveSounds (2006)
Timberlake achieved his second consecutive Hot 100 No.1 with "My Love," a song that has been defined by many as the sequel to "Cry Me a River." Although borrowing from the same insistent staccato beats, "My Love" is rather a happier, snappier version of it. Gone is the desire for retaliation — Timberlake is now focused on the sweet highs of a promising relationship.
"All I want you to do is be my love," he sings over masterful production by Nate "Danja" Hills and Timbaland, who infuse the track with quirky distortions, beatboxing and a slow beat juxtaposed to Timberlake's frenzy. Atlanta rapper T.I. also adds contrast to the track, delivering a stack of verses that contrast Timberlake's lyrics and add to the multifaceted perceptions of love. If Timberlake's lines represent one's heart soaring with possibility, the other elements of the song keep it grounded, reminding us that true love runs steady.
"What Goes Around... Comes Around," FutureSex/LoveSounds (2006)
The true "Cry Me a River" sequel lays on the grandiose "What Goes Around... Comes Around." Despite the single's lofty arrangements and a cinematic music video starring Scarlett Johansson, Timberlake is still heartbroken.
However, instead of seeking revenge by his own hands, he now trusts karma to take care of his lover's wrongdoings. The circular, haunting motifs of the lyrics are repeated through synth loops and Turkish strings.
"What Goes Around... Comes Around" is one of FutureSex/LoveSounds' standouts, bridging the catchy sounds of Justified with more experimental nuances. It also seemed to resonate with listeners, as it landed the singer his third consecutive chart-topper.
"LoveStoned," FutureSex/LoveSounds (2006)
While violins surely can provide a sultry mood, it's not often that they will be paired with beatboxing and funky bass — which makes "LoveStoned" a peculiar feat.
One of Timberlake's most provocative tracks off FutureSex/LoveSounds, it could also be defined as a bolder cousin to 2002's "Rock Your Body" due to its rushing, disco-esque energy. Along an easygoing progression, it carries Timbaland's trademark vibes and fiery lyrics about what the internet would call a "baddie" nowadays ("She's bad, and she knows," Timberlake sings).
Originally named "LoveStoned/I Think She Knows (Interlude)," the track swiftly slows down in the last two minutes, where an Interpol-inspired guitar solo flourishes, offering a hazy conclusion to an innovative pop expedition.
"Suit & Tie (feat. Jay-Z)" The 20/20 Experience, (2013)
After wrapping up his highly successful FutureSex/LoveShow world tour in 2007, Timberlake took some time off to focus on acting and producing for other musicians. Following a six-year musical hiatus, he released his third studio album in 2013, The 20/20 Experience, led by the steamy "Suit & Tie," featuring rapper Jay-Z.
The single is anchored by samples of Sly, Slick and Wicked's 1972 song "Sho' Nuff" and swirls around a matured, glistening R&B production by Timberlake, Timbaland and J-Roc. It's the most sophisticated that Timberlake has sounded, accompanied by a fittingly classy, black-and-white music video — which won a GRAMMY for Best Music Video in 2014.
"Mirrors," The 20/20 Experience, (2013)
The second single off The 20/20 Experience, "Mirrors" was written back in 2009 and inspired by Timberlake's relationship with wife Jessica Biel, as well as his grandparents' six-decade marriage. Although the sounds harken back to "Cry Me a River" at times, the lyrics reveal that Timberlake is no longer bitter, but instead very much in love: "Now, you're the inspiration of this precious song/ And I just wanna see your face light up since you put me on/ So now I say goodbye to the old me, it's already gone."
Paired with an emotional music video, "Mirrors" is a defining landmark in Timberlake's discography, showing how personal growth impacted his music for the better. Alongside trusty producers Timbaland and J-Roc, he proved that it's possible to turn an eight-minute prog-soul aria into a timeless, effortlessly catchy love song.
"Drink You Away," The 20/20 Experience – 2 of 2 (2013)
Six months after the release of The 20/20 Experience, in September 2013, Timberlake dropped the second half of the album, The 20/20 Experience – 2 of 2. Out of its four singles (which also included "Take Back the Night," "TKO," and "Not a Bad Thing"), "Drink You Away" stands out for its adventurous streak.
Here, Timberlake recalls his Southern roots, spinning a pop twist on Memphis soul and country rock riffs. "I've tried Jack, I've tried Jim/ I've tried all of their friends/ But I can't drink you away," he sings, matching love pains to alcoholism. Once again working with producers Timbaland and J-Roc, he daringly explores new scenarios, ultimately proving that his talents can't be restrained. (The track also teased Timberlake's later collab with country crooner Chris Stapleton, as the pair mashed "Drink You Away" with Stapleton's "Tennessee Whiskey" at the 2015 CMA Awards.)
"CAN'T STOP THE FEELING!," Trolls (2016)
Timberlake's career may have firm pillars in experimentation, but 2016's "CAN'T STOP THE FEELING!" showed that he is also a master in well-rounded bubblegum pop. In 2016, after voicing the character Branch and serving as the executive music producer for the movie Trolls, Timberlake worked with Max Martin and Shellback for the soundtrack's lead single.
The result was a simple, yet contagiously happy disco track that quickly hit No. 1 on Billboard's Hot 100, followed by several other countries' charts. "CAN'T STOP THE FEELING!" was also the top-selling song in the U.S. that year according to Nielsen Music's Year-End Report, and quickly achieved an omnipresent status; the song remains a global staple today.
"Young Man," Man of the Woods (2018)
After another long break between albums, Timberlake released his fifth LP, Man of the Woods, in 2018. The title references the meaning behind his firstborn son's name, Silas, and features some of his most experimental trials to date, despite enlisting the same longtime producers like the Neptunes and Timbaland.
As Timberlake's personal life changed with marriage and parenthood, so did his music. He plunged even deeper into his Tennessee origins and the country music of his childhood, as evidenced in singles "Filthy," "Supplies," and the Stapleton-featuring "Say Something."
However, the most essential song to understand Timberlake's current moment is the sweet, deeply personal "Young Man." It closes the album on a vulnerable note, showing the singer not as a superstar, but as a devoted father passing on his teachings. Vocal snippets from both Silas and Jessica Biel make it even more special, framing a fleeting moment into eternity.
After seeing Timberlake grow from a teenager himself to raising his own family, there's a full-circle element coloring his next steps with much expectation. What will be his next reinvention? If Timbaland's words are true, luckily we won't have to wait too long to find out.
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