From Mouseketeer to boy-band heathrob, R&B superstar, and now lumbersexual cabin-dweller, Justin Timberlake has reinvented himself more times than his idol Michael Jackson’s face—and that’s just his music career. From playing Napster cofounder Sean Parker in the Oscar-winning movie The Social Network to voicing the character Artie in Shrek the Third, JT has become a well-regarded actor on the Hollywood circuit (even if he did just star in Trolls). Add to that the fact that he bought music-based social platform Myspace, owns his own fashion line, and has created his own brand of tequila, and there’s hardly a branch of entertainment that he hasn’t touched. The multitalented megastar will bring his Man of the Woods show (and hopefully that weird Superbowl camo suit and fringe-lined jacket) to Rogers Arena, where he will be playing back-to-back concerts tonight (February 14) and tomorrow (February 15).
FOUR-WHEEL FETISHIST Few things in this life are more puzzling than the hobby of collecting cars. Who needs a Porsche in the driveway, a Hummer in the garage, and a Tesla behind the guest house. And don’t even get us going on the insurance costs? Still, like many celebrities with no shortage of disposable income (Jay Leno, Jerry Seinfeld, David Beckham), Justin Timberlake is of the opinion that one can never have too many automobiles. He was already well on his way to assembling a four-wheeled fleet back in his *NSYNC days; in a 2001 Rolling Stone profile of the multi-platinum boy band, writer Toure revealed that Timberlake owned a Plymouth Prowler, Dodge Viper, Audi TT, Porsche 911, BMW M Roadster, a Mercedes, and a Cadillac Escalade complete with a “PlayStation 2 and TVs in the headrests”. In recent years, his cars have included a BMW 7 Series, Audi A1, Audi S5 Cabriolet, Jeep Cherookee, and most covet-worthy of all, a vintage Pontiac GTO. Admirably, however, according to People magazine he’s often found toodling around L.A. in a 2002 Volkswagen Jetta. No matter what he’s driving, he’s arguably smarter than all of us, namely because there’s zero chance he has to spend 25 minutes looking for his car keys whenever it’s time to leave the house.
POWER TO THE POWER PEOPLE Ever see a couple who makes you think that there’s no hope for the rest of us? Step forward, Justin Timberlake and Jessica Biel—who are serious frontrunners for the most gorgeous people tethered to each other on the planet. According to urban legend, the two met when Timberlake, after escaping the clutches of amateur fartsmith Britney Spears, ran out of gas (get it?) with Cameron Diaz. After a four-year run with Diaz, Timberlake was back on the market when friends introduced him to Biel. Despite being one of the world’s most eligible bachelors, JT had his work cut out for him when it came to setting up a first date. Keeping in mind this was 2006, before the complete domination of Twitter, Instagram, and dick-pic texting, he got to say yes the way folks did in ancient times. While promoting the film Trouble With the Curve, Timberlake told reporters “I did it the old-fashioned way—by telephone. That’s something I learned from both my stepdad and my grandfather—that there is a thing called chivalry and it doesn’t have to die with the birth of the internet. The way I see it, if you’re asking a girl out on a date, it’s only right to do it in a way that she can hear your voice. I had to be pretty persistent in order to get her to say yes. But I have a fair amount of tenacity and if I want something I stick to it. And in the end she agreed.” Flash forward a decade and a bit and, despite a brief pre-marriage separation in 2011, they remain among the most powerful couples on the planet. Not to mention seemingly genuinely decent people—note that when they stopped by the Lebron James-founded I Promise School for disadvantaged children in Akron last fall, they spent the afternoon sitting on the floor with the kids, not standing on the sidelines with a bodyguard.
MAN OF THE WEB Do you like YouTube? Of course you do. Everyone likes YouTube. Where else would you go to find half-remembered Saturday-morning cartoons from the ’90s and every music video ever made? Well, you can thank Justin Timberlake for it. Not directly, mind you. But you probably recall a certain now-infamous “wardrobe malfunction” dubbed “Nipplegate”. You know, that moment during the half-time show of the Super Bowl in 2004 when, during a performance of “Rock Your Body”, JT ripped part of Janet Jackson’s top off, partially exposing her right breast. According to YouTube co-founder Jawed Karim, it was frustration at not being able to easily find a clip of Nipplegate (and other then-current events) online that inspired him and his two partners—Chad Hurley and Steve Chen—to launch the world’s biggest video-sharing site. Timberlake may have inspired one cyber-success story, but even he couldn’t stop the juggernaut that was Facebook. In 2011, Timberlake and some partners bought Myspace and attempted to make it relevant again, which was already a lost cause by that point. Myspace was the world’s most popular social-media platform from 2005 to 2009. As of last January, though, it was ranked 4,153 by total Web traffic. Perhaps ironically, Timberlake played Facebook’s first president, Sean Parker, in The Social Network—but that’s a whole other topic.
BRITNEY WHO? When he was promoting his debut solo LP, 2002's Justified, Timberlake told anyone who asked (including, famously, Barbara Walters) that, no, absolutely none of the songs were about his breakup with Britney Spears. Spears, you may recall, was one of Timberlake’s fellow Mouseketeers on The All-New Mickey Mouse Club. (Suggesting that its casting director should be given some sort of lifetime achievement award, other future stars on the show included Christina Aguilera, JC Chasez, Keri Russell, and Ryan Gosling.) Long after retiring their Mouseketeer jackets, Timberlake and Spears dated from 1999 to 2002, leaving a trail of matching distressed-denim ensembles behind them. It has long been rumoured that the relationship’s messy dissolution—she allegedly cheated on him with one of his friends—did in fact inspire the song “Cry Me a River”. In his 2018 book, Hindsight: And All the Things I Can’t See in Front of Me, Timberlake wrote, "I've been scorned. I've been pissed off. I wrote ‘Cry Me a River’ in two hours. I didn't plan on writing it. The feelings I had were so strong that I had to write it, and I translated my feelings into a form where people could listen and, hopefully, relate to it. People heard me and they understood it because we've all been there." Timberlake has never come right out and admitted that Spears is the subject of “Cry Me a River”, but he does stalk and exact sleazy revenge upon a look-alike in the song’s video, so you be the judge.
ALL YOU KNEAD IS LOVE: If you’re a big enough JT fan that you’ve spent time wondering what the star enjoys for breakfast, we can confirm that it’s unlikely to be French toast. In 2000, a fresh-faced Timberlake left a half-eaten, egg-soaked mess behind at the studio of a New York-area radio station. Spying an investment opportunity, the DJ saved the two pieces of toast and put them up on eBay. After a lengthy bidding war, the dish was purchased by *NSYNC superfan Kathy Summers, then 19, who paid $1,025 for it. When asked what she was planning to do with the toast, she responded that she’d “probably freeze-dry it, then seal it…then put it on my dresser.” Of course.More