When it comes to life advice, I generally prefer to get mine from a crusty, hardscrabble old person—Bea Arthur, preferably. But if Oprah tells us that Justin Timberlake is a modern master, who are we to deny the teachings emerging from his experience as an entertainment icon? And plus, in his 33 years he has persevered through clown hair, a legendary denim suit, and—dare I say it!—cramped feet to get where he is today (doling out wisdom against a classy dark gray backdrop on Oprah's Master Class).
Before going through a chronological inventory of his career (which is, in fact, quite impressive), JT tells us that making it look easy is the hardest thing he's ever done. He spends lots of time in front of the mirror, or practicing his instrument (did you guys know he played guitar?), or dancing until his feet cramp. It's a hard knock life! But his parents instilled in him that you have to put in 115 percent to get a 90 percent return. So if, like me, you're hovering at around 60 percent effort on a good day, that's not fantastic news.
In his early years, Justin Timberlake always felt like he was different. Growing up in Memphis, a melting pot both culturally and racially, he never fit in with the black kids because he was white (sorry to drop that bombshell on you so casually if you were not aware!) and never fit in with the white kids because he liked "black music." He actually starts off the episode saying that he was called the f-word, the w-word (rhymes with the n-word), and a cracker (the other c-word) which are all things you can say with no beeping on Oprah's Master Class in the context of poignant life lessons ONLY.
He began to "find himself" in church—not because of any spiritual awakening, at least that he mentions, but because it's a good place to get your stage chops. After all, people say "Amen!" regardless of the quality of your performance. JT tells us that he learned more about himself by being on stage than in interacting with other humans, which is one of those things that very famous people say that makes you realize how even if they appear totally normal and awesome (as JT does, I think), they're probably crazy and can't be trusted.
And then—thrill of a lifetime!—we get to see JT when he competed on Star Search. He was a little kid in a big cowboy hat, and tells us that even though he wanted to sing "When a Man Loves a Woman," the producers liked him doing Garth Brooks better. And, I mean, a ten year old singing "When a Man Loves a Woman" is creepy! Those producers were not wrong, even if they were stifling his true musical inclinations. The high point of the experience for Justin was meeting Ed McMahon. The low point was losing in the first round to a doily-wearing little girl with a huge bow in her hair. OR WAS IT?
In fact, nay! If JT had won even one round on Star Search, he would have missed open call auditions for the Mickey Mouse Club. When a door closes, somewhere a window opens! In Orlando, usually! That is one of Justin Timberlake's profound life lessons! He says that this experience taught him all about success and defeat. And, I mean… He literally failed at ONE THING when he was like, ten, and then got cast on a TV show. What brutal early dues-paying years he had! Respeito!
The biggest bombshell that I got from this whole episode is that Ryan Gosling was on the Mickey Mouse Club! Does everyone know this but me? I mean, I knew about Britney and Christina and JC Chasez and Keri Russell, but this Ryan Gosling news is a revelation. It reminds me that I have to work harder—probably putting in about 115 percent effort—to expand the base of useless trivia in my brain. Justin Timberlake's life lessons are relevant in real time! Oprah's going to be so pleased about this.
The Mickey Mouse Club lasted only two seasons, but during that time JT learned all about hard work and how to put a weekly show together—something that's come in handy as a Saturday Night Live mega-host. After MMC's cancellation, he went back to school and tried to be normal for a little bit, having to overcome the stigma of being "that kid from the TV show." Around this time, his mom doled out another poignant life lesson, which is that he had a gift, and that gift would make his life more challenging because it would test his character—he would have to work hard to realize that he wasn't better than anybody else. He does later say, "When you look at me, you should understand: I am America," so you can gauge for yourself whether or not this message was internalized.
And then we get to the 'N Sync years! (And is anything more confusing than properly punctuating 'N Sync? I am going to put 115 percent effort into getting it right for the remainder of this piece.) Justin was fourteen when the band was put together, and it was truly the apex of his clown hair. 'N Sync toured Europe, got huge, and their first record went diamond (that's ten million sales). And then each of the band members got a check for $10,000, and quickly realized that shit was not right. As Justin says, "That was my first lesson in the music business."
We sadly do not go deeply into the creepiness that is professional miscreant/boy band Svengali Lou Pearlman, but are reminded how the band took Lou to court and won the rights to split from him and continue using their puzzlingly constructed name. This whole experience taught Justin—at age 17!—to keep an eye on your damn money, which is for sure a life lesson worth remembering.
At the release of their second album, No Strings Attached, 'N Sync got bananas famous, playing stadium shows and closing down Times Square with their TRL appearances. And it was at this point that JT starting getting an urge to step out on his own, for artistic reasons and probably also because he is no dummy. It was a bittersweet move, he says. (Chris Kirkpatrick would probably focus more on the "bitter" part of the equation.)
The first indication that he was breaking out in different directions was a song called "Gone," which Justin had written for Michael Jackson. He got word that Michael turned it down, so 'N Sync put it on their album. But THEN Michael heard it and called Justin on the phone to say he wanted to record it as a duet. But it was too late! The album was already out, and Michael Jackson was not into doing an "'N Sync featuring Michael Jackson" kind of deal. He wanted a JT duet or bust. Justin says he literally was punching himself in the head during this call, which is maybe what finally straightened out his hair. So even though "Gone" ended up being a moderately enjoyable 'N Sync song, the incident—which has never been told before, probably because it's not all thaaaaaat interesting—gave Justin the confidence to break out on his own.
All of this led to "SexyBack," which people thought was a joke and/or not really him. The president of his label thought it would never work. But Justin believed in the song, and "believed in what it made other people do." Hump the walls at the club? What did that song make people do? Anyway, it was obviously a huge hit, and JT learned to trust his instincts—another wholly original and powerful life lesson for us all! He also advocates for challenging yourself, as he has done with his burgeoning acting career and "Bring it on down to Veganville" sketches.
Justin's big marriage advice is that, "Just because you get married, it doesn't mean you stop dating." He doesn't clarify whether he means dating your wife or dating other attractive ladies, so I'm not as enthusiastic as Oprah when she pops up to comment on how sweet this is. I am also totally mad that we didn't get any insight into The Britney Years!
The best story of the whole thing—one that the producers clearly prodded him into talking about—involves the 2003 Toronto Rocks festival, in which the Rolling Stones personally invited JT to perform. He was on a bill including the Stones, AC/DC, Rush and The Guess Who, and quickly started to realize that one of these things was not like the other. He kicked off his set with "Cry Me a River" and was instantly pelted with beer bottles. And in fairness to that crowd, he WAS wearing camo pants and a trucker hat.
Despite the attempts of the show's MC to get him off the stage, Justin finished out his set—something of which he's very proud. He did try to get out of performing a number with the Stones later, but Mick insisted that he joined them. And then JT realized that people were throwing bottles at the Stones, too, and figured out that they didn't just hate him—they hated him and ALSO were just very drunk.
Eventually, Keith Richards took matters into his own hands. He went up to the crowd, looked at a guy who launched a bottle right between JT and Mick Jagger's heads, and started beating on his chest in a primitive display of dominance. I guess it worked? So that's a life lesson, too? And then, in an impressive display of professionalism, Keith went right back to the riff in whatever song they were playing. And all this makes me think… When are we getting Oprah's Master Class with Keith Richards?