WTF Happened to Justin Timberlake?

It’s never happened to me, but I’ve heard that other people sometimes don’t feel like the coolest person in the room. Lately, it seems like he spends more time in hot water, but at one point, Justin Timberlake seemed like the coolest guy on the planet. Despite his massive fame and success, Timberlake always felt like he was in rooms with more comfortable and confident people than he was. So, in one of the most lucrative forms of overcompensation ever, he wrote and released the 2006 smash hit “SexyBack”, an anthem declaring that he was redefining cool on his own terms. And in a lot of ways, he did. The song dominated radio, clubs, and pop culture, a testament to Justin Timberlake’s creativity and drive, making him the powerhouse he became. It hasn’t always been perfect, and we’ll talk about that, too, but fewer artists have matched Justin Timberlake’s peak or longevity.

But before we go there, let’s go back to where the beginning began, when he was born ON HIS BIRTHDAY, January 31, 1981, in Memphis, Tennessee, a town with a rich musical history. And since we’re talking Tennessee, let’s be honest, viewer—you’re the only ten I see. If you’re watching this video around when it drops, happy birthday to Justin! He joined The All-New Mickey Mouse Club in 1993 for its sixth season, where he met his future *NSYNC bandmate JC Chasez, along with Britney Spears, with whom he’d form a checkered history, Christina Aguilera, Keri Russell, and Ryan Gosling.

Justin Timberlake, along with JC Chasez, Joey Fatone, Lance Bass, and Chris Kirkpatrick—yeah, the one you always forget, formed *NSYNC in 1995 under the exploitative thumb of Lou Pearlman. Pearlman had a model where he’d prop up these various pop groups, including the Backstreet Boys, and give them pennies on the dollars they earned working brutal schedules with few days off. Luckily, bosses in other industries never do that.

*NSYNC got their feet wet in Europe before releasing their self-titled debut album in the U.S. in March of 1998. Later that year, they were Home for Christmas, an underrated Christmas album. After a legal battle with Pearlman, *NSYNC released their magnum opus, 2000’s No Strings Attached, which was one of the best-selling albums of the decade and held the first-week US sales record for 15 years. The album helped them break out of the Backstreet Boys’ shadow with a more R&B-and hip-hop-infused sound that the band insisted on. Seriously, if you were a kid around this time, you could gain or lose friends based on whether you claimed *NSYNC or the Backstreet Boys. It was a war. 2001 marked the release of *NSYNC’s final studio album, Celebrity. In a tale as old as music, it was around this time that the band began to grow apart creatively, with Timberlake later saying the other band members just didn’t want it as badly as he did. He also wanted to focus on his solo career, so he said Bye Bye Bye to the band. In November 2002, he released his debut solo album Justified. Get it? JustIN/JustIFIED? You get it. The biggest hit off that album was Cry Me a River, which features lyrics about a relationship that failed due to cheating and a music video with an actress who may be meant to look like Britney Spears. I guess it was his way of saying, “I’m into brunettes, now.” The album would net him a Grammy for Best Pop Vocal Album and Best Male Pop Vocal Performance.

You may remember that Justin Timberlake performed with Janet Jackson at the Super Bowl XXXVIII (38) halftime show in 2004. In a strange grasp at relevancy, Timberlake exposed Jackson’s breast, in an incident that came to be known as “Nipplegate”, because, ever since Watergate, every controversy has to get a ‘gate’ stapled onto the end. It all seemed just a bit too choreographed to be accidental, and despite an Oscar nom and a handful of Emmys, nobody was buying Justin’s ‘it was an accident’ defense. The conversation that dominated the news cycle was about who was complicit and how much they knew going in. Gotta find someone to blame for showing part of a boobie during my sacred sports ball game.

And it was around this time, burnt out by the music-making process, that Justin Timberlake began his screen forays, starting with the crime drama Edison in 2005, a movie so forgettable that even Morgan Freeman couldn’t save it—and that guy narrated March of the Penguins. The burnout didn’t last long, though, because in 2006, Timberlake declared that he was bringing sexy back with his second solo album, Future Sex/Love Sounds. The album’s slick, eclectic, interlude-heavy style made it arguably his best, earning him multiple Grammys, including Best Rap/Sung Collaboration, Best Male Pop Vocal Performance, and two for Best Dance Recording.

2006 is also when Justin Timberlake began his heralded appearances on Saturday Night Live, which would earn him four Emmys. Yeah, Dick in a Box won an Emmy. And it totally deserved it. It was genius—transcending pop culture into the realm of a cultural phenomenon. The Lonely Island guys have all the comedic and musical talent worldwide. Still, Timberlake’s participation lent legitimacy, novelty, and celebrity, which helped propel it into the upper echelon of musical comedy sketches. It’s catchy, subversive, and a sharp commentary on R&B tropes—with a little something extra for the movie nerds. (Barry Levinson’s Diner from 1982). The digital shorts Motherlover in 2009 and 3- Way (The Golden Rule) in 2011, featuring Lady Gaga, continue in the same vein and are brilliant in their own ways.

Timberlake’s role in Alpha Dog in 2007 showed he may have some bonafide acting chops. That busy year also included appearances in Black Snake Moan, Samuel Jackson’s other snake movie, and Southland Tales, where Timberlake is barely recognizable in an overwrought narrator role. It must have been green-lit in between Donnie Darko’s initial release and the director’s cut when people still thought Richard Kelly knew what he was doing.

After roles in Shrek the Third in 2007, The Love Guru in 2008, and The Open Road in 2009, Timberlake toon on what is perhaps his definitive acting role, as Sean Parker in 2010’s The Social Network. The performance earned critical acclaim and award nominations, showcasing a range beyond his usual musician typecasting. He brings a subtle fragility masked by charming bravado, making him the perfect foil to Jesse Eisenberg’s Mark Zuckerberg.

Justin Timberlake voiced Boo Boo in the 2010 3D animated Yogi Bear, which didn’t need to be made. His 2011 included roles in Bad Teacher, Friends with Benefits, which is pretty good if you’re into rom-coms, and In Time, which has a cool, if underdeveloped, concept. 2012 brought us Trouble with the Curve, which has a little trouble getting off the ground, and 2013 brought us Runner Runner, which I’d say to run away from unless you really like shallow thrillers. The Coen Brothers’ Inside Llewyn Davis is fantastic, but it meant much more for Oscar Isaac’s career than Justin Timberlake’s.

2013 also brought us Timberlake’s third solo album, The 20/20 Experience, and its continuation, The 20/20 Experience – 2 of 2. Justin Timberlake + The Tennessee Kids, the 2016 Jonathan Demme-directed concert film, is of the best you’ll see. That same year featured Timberlake in Trolls, wherein he voiced the cynical Branch opposite Anna Kendrick’s unflinchingly positive Poppy. Timberlake’s contribution to the soundtrack – Can’t Stop the Feeling, which, if you had young kids around this time, you couldn’t stop playing, earned him Golden Globe and Oscar Noms for Best Original Song and a Grammy for Best Song Written for Visual Media. The Trolls movie became a cultural phenomenon, spawning two-holiday specials, two animated series, and merch out of the wazoo. Timberlake returned for two sequels: Trolls World Tour in 2020 and Trolls Band Together in 2023 – the latter featuring a reunion with his *NSYNC bandmates for a song on the soundtrack.

Justin Timberlake starred for Woody Allen in 2017’s Wonder Wheel, which features gorgeous visuals and an earnest performance from Timberlake if not a cohesive whole. In early 2018, he released his fourth solo album, Man of the Woods. And somehow, the Super Bowl invited him back for their halftime show so he could promote it. This was the beginning of a redemption tour, of sorts, which also included a public apology on Instagram to Britney Spears and Janet Jackson, spurred by renewed scrutiny from a New York Times docuseries and the #MeToo movement.

This reflective vulnerability likely informed his performance in 2021’s Palmer, where he delivers a restrained, emotionally nuanced performance that speaks to his growth as both an actor and a person. The film’s reception and the equity he gained for his part in the massive Trolls franchise served to endear him to the public for a time. He even appeared with his former *NSYNC bandmates to present at the VMAs in 2023. But nothing to this point was going to stand against the accusations levied against him in Britney Spears’ 2023 memoir The Woman in Me. Rampant cheating, pressuring her into an abortion, and, worst of all, breaking up with her via text message! LEAVE BRITNEY ALONE!

Then, not long after the release of his album Everything I Thought It Was in 2024, Justin Timberlake was arrested for driving while intoxicated in The Hamptons, New York, after running a stop sign and veering out of his lane. As part of his plea deal, he was made to give a ridiculous public apology that came off like it was written for SNL.

Looking forward, I see that perceptions of Justin Timberlake seem to depend on who you ask. His recent controversies were expected to negatively affect ticket sales for his Forget Tomorrow World Tour, but it’s been the fastest-selling tour of his solo career. He’s been filling massive arenas, adding extra shows, and, apparently, proving that people will forgive a lot if you’re hot and talented. Even his *NSYNC bandmates showed up for his LA concert—maybe a tease that everyone’s second-favorite boy band has something big in the pipeline. And if you don’t like the sound of that, Cry Me a River.