From ‘SNL’ To Silas, 11 Things I Learned From Justin Timberlake’s Book ‘Hindsight’

I’ve been a fan of Justin Timberlake for more of my life than I haven’t. In fact, 2018 marks the 20th year of listening, watching, and dancing to the man who has provided endless entertainment and joy and of course a few moments of frustration and annoyance, but hey, that’s bound to happen.

So when he released his book Hindsight at the end of October, I stopped by Barnes & Noble to pick up the approximately 30 pound book (which was not prominently displayed but stacked on a lower shelf, rude) filled with gorgeous pictures, personal details, and philosophical revelations he’s picked up over the years. While a few events and people come to mind that I’d love to know his true thoughts about, the notoriously private JT gives just enough of a peek into his life behind the scenes to provide several insightful and delicious nuggets of info and wisdom (and maybe even a little bit of nonsense, oops, we judge the ones we love). Here are 11 things about him I didn’t know before, but I’m glad I do now.

1. He listened to “Bohemian Rhapsody” 10 times in the dark

When he was nine years old, he got his little hands on Queen’s A Night at the Opera album and once he heard “Bohemian Rhapsody” for the first time on his record player, he was hooked. “I listened to the song, and as soon as it was over, I needed to hear it again. I locked myself in the room and turned the blinds so the space would be completely dark, and then I turned off the light. I listened to the song the whole way through in the dark. It blew my mind. I turned the lights back on and adjusted the needle, and let it go again. I probably listened to the song ten times in a row.” No word on if he’s seen the Rami Malek-led movie yet though.

2. The first time he met Dave Chappelle was at Star Search

When little JT headed to Orlando to compete on the talent show, he ran into future friend Chappelle for the first time. “He was there because Star Search had a comedy category. That was the first time I met him, so there’s that weird fact. And hey, we both did all right for ourselves!”

3. He did pageants

Look, I should’ve known this, but I don’t believe he’s ever used that word before: pageants. It was always talent competitions. As JT explains, “You could only do the talent competition if you participated in the whole pageant, though, so I did it. All the girls and me. I got a lot of shit for that, but I also got some great experience, because you always have to answer that pageant question.”

And when he was posed with such a pageant question during the big MMC audition and asked by a producer, “Why do you want to be on the Mickey Mouse Club?” he recalls, “I said very drily, ‘I’m in it for the money.'”

“I don’t know why I knew that would be funny to an adult. But it was.” What a little squirt.

4. He went on a joy ride of sorts with Ryan Gosling

Of course these two rascals bonded while they starred on MMC together, but this memory from JT is especially adorable or annoying, depending on who you ask, I suppose. “Ryan and I once stole a golf cart and drove it to the employee entrance for the Tower of Terror. We went on that ride twelve times in a row.” That’s too many times, bro.

5. Everyone from Brad Pitt to his grandmother’s friend inspired his SNL characters

JT says the “Bring it on down to [Whatever]ville” Saturday Night Live sketch was originally inspired by Brad Pitt himself. “When we were coming up with ideas for skits for the first hosting gig, I knew people would want to see me do physical, musical comedy. Around that time, there was this story going around about Brad Pitt’s first job in Hollywood, that he had been the El Pollo Loco chicken. The legend goes that he’d dress up in a chicken costume and stand out in front of El Pollo Loco, dancing around, waving his arms at traffic, flipping his sign and saying “Come to El Pollo Loco.” They paired that with musical parodies and the rest is history.

As for his Classic Peg character in the Target Lady sketch with Kristen Wiig, well that one hit a little closer to home. “I based Classic Peg, very simply, on Bea Arthur’s character Dorothy on The Golden Girls and my grandmother’s friend, who always had this certain expression on her face, this funny way of conveying a story.”

“I saw her at our church every Sunday. She had a huge, hearty laugh that shook her whole body,” he says.

Wiig was especially impressed with the way he moved his shoulders, but it’s like, who isn’t?

6. The one thing he had in common with Sean Parker

When he was preparing to take on his role in The Social Network, JT says, “I had to walk in with respect for the character. All I needed was one thing where I could say, ‘I have something in common with this character.’ For Sean Parker, it was easy. Ambition. That was what touched me.” You know what’s cooler than a million dollars? Ambition.

7. This Keith Richards power move

At a SARS benefit concert in Toronto, JT noticed he was the only pop act on the bill, and so did the angry AC/DC fans. They not only hurled bottles of pee at him, but at The Rolling Stones as well. Luckily, someone knew exactly what to do. “When Keith (the Keith Richards) saw what was happening, he walked to the front of the stage, banged on his chest like an angry gorilla, and challenged the culprits to throw something at him. Said culprits cowered and decided it was not in their best interests to continue.”

8. “SexyBack” throws CoolAway

Ok, so I did know most of the story of “SexyBack” but I’ll always be interested in hearing how this genius piece of music came to be. It’s also fairly well-known that JT’s record label had no interest in releasing the unique song as the first single off his second album, FutureSex/LoveSounds. When they were like, “Mmm, let’s not,” JT learned (as did we) that his mom used to tell his teachers the one way of getting him to do something in school was simply “tell me that I can’t do it.”

JT remembers that “The record company challenged me.” They said of “SexyBack”, “It’s too fast. You’re not even signing.” Ok, but we certainly were all dancing, and in that don’t-care-who’s-watching kind of way. “It made everybody take off their cool,” JT proudly states.

9. How Jessica and Silas came to be

Though he mentions this in his song “Higher, Higher” JT confirms in the book that when he first met future wife Jessica Biel at a party, “We talked that night. The DJ played “Lucky Star” and we danced. And then she was gone.” He played it cool until she came to his concert in San Diego and the long-distance phone friends soon turned into much more. She ended up joining him on the European leg of his tour where they shared room service and Scrabble games and it’s like, stop being so damn cute you two.

I’m actually kind of surprised he shared such a personal detail here, dedicating a page to the moment he found out he was going to be a dad. As he Facetimed with Jessica after a concert stop in Detroit, “She answered with this look on her face, and I knew exactly what she was going to say. Instead, she just held up the pregnancy test, and we both started bawling.” Any grinch can agree, that’s really, really, sweet.

10. Gin and tonics and Jimmy 

“We find each other endlessly amusing,” JT says of his pal, and it’s like, duh. We’ve seen this in action.

What we might not know about this duo is that a couple of gin and tonics and their extreme paling around led to “The History of Rap” bits he frequently performs on The Tonight Show with Fallon.

“We also have some bits inspired by a bottle of Jagermeister. Don’t worry, you wont be seeing those on TV,” he promises. And that’s kinda too bad. Can we see them on the internet?

11. That Netflix special really was special

Justin Timberlake and the Tennessee Kids was released on Netflix in 2016 and directed by the legendary Jonathan Demme. Filmed at JT’s last tour stop on The 20/20 Experience Tour in Las Vegas, the concert special wowed audiences at the Toronto International Film Festival before hitting the streaming platform, and there’s a reason it looks different from many other concert specials.

“He said, ‘You know how concert films always cut back to the audience response? We’re not going to do that here. All the magic is happening onstage. There’s a real electricity between all of you and what you’re creating up there on that stage every night. That’s the show.'” Demme was right, and that’s what makes it such a fun visual experience.

Demme sadly passed away in April of 2017, but JT recalled, “He would call me up randomly and say, ‘Hey, remember that conversation we had? I just wondered how you were doing.’ He was one of the most beautiful people I’ve ever met.” It’s one of the most touching dedications in the whole book, and really lovely that the film will live on for many to watch and dance along with.

Where to stream Justin Timberlake and the Tennessee Kids