He and Ryan Gosling caused some trouble on the Mickey Mouse Club set.
Following the charming story of how he landed a spot on the Mickey Mouse Club – which involved telling casting director Matt Casella "I'm in it for the money" – Timberlake admits that he wasn't always charming behind the scenes: “We had employee cards that gave us access to the theme parks for free. 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. We got reprimanded for that. It was worth it.”
*NSYNC faced some tough crowds in the early days.
Timberlake says there were some "very weird parts" during the height of *NSYNC. One of the most memorable? A performance at a Scandinavian festival where they weren't even supposed to be on the bill. "The festival consisted of a bunch of heavy metal acts and this 'up-and-coming boy group from the USA.’ We spent our twenty-five-minute set dodging glass bottles being thrown at us by tall, blond, heavily tattooed people.”
So did solo Justin.
Once Timberlake went solo, Mick Jagger recruited him for a SARS benefit show alongside The Rolling Stones, AC/DC and the Guess Who. As the only artist on the roster considered "pop," he knew he was in for trouble. "Before we walked onstage, I remember saying to my band, ‘Hey, guys, I can’t imagine this is going to go well.’ And then we prayed. I walked onstage to beer cans and bottles of urine being thrown at me. Bottles. Of. Urine."
He later joined The Stones on stage for "Miss You," which again led to flying bottles – until Keith Richards came to the rescue. "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 interested to continue."
He wrote “Cry Me a River” in two hours.
If you thought Timberlake was going through something when he wrote "Cry Me a River," you were right: "I didn’t plan on writing it," he explains in the book. "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.”
He was furious about Justified being labeled a “pop” album.
When Timberlake started working on Justified, his goal was to make a proper R&B album. When reviews came in calling it pop, it bothered him "way longer than it should have," he admits. "I had a vision for it. I wanted people to get that vision. I was also twenty-one and precious as hell. It’s clearly a pop album."
“SexyBack” was inspired by David Bowie.
Timberlake had been listening to Bowie for two weeks straight before going into the studio with Timbaland for the session that spawned "SexyBack." He was particularly inspired by "Rebel Rebel": "That’s what I wanted for ‘SexyBack. I wanted to create something that made me feel like David Bowie made me feel when he sang ‘Hot tramp, I love you so!’ (With the exclamation point.)”
He and Jessica Biel started officially dating right in the middle of his FutureSex/LoveSounds Tour.
Just before jetting off to Europe for three months, Timberlake told Biel he wanted to be exclusive. She agreed and eventually flew to Europe to spend two weeks with him on the road: "We were going to different cities, having a ball, with room service and pay-per-view and great dinners. And Scrabble.”
Most of his sketches with Jimmy Fallon are just what they do when they’re hanging out.
The pals' now-iconic "History of Rap" sketch came to life after they both made an appearance on an episode of SNL with Amy Poehler. With a couple of gin and tonics in their system post-show, Timberlake recalls Fallon mentioning the viral YouTube video "Evolution of Dance," and the rest is history: "That led us to a seriously unserious conversation about why there was no history of rap. Which led to a rap competition. Which became Jimmy and me rapping classic hip-hop songs from the seventies and on. Which became 'The History of Rap.'"
He’s keeping his son Silas out of the spotlight for personal reasons.
Timberlake references his son throughout the last quarter of Hindsight, talking all about what he's learned from fatherhood in a section titled "A Man Becomes a Man." He writes that he and Biel wanted to keep Silas to themselves for a while after he was born, and even now, keeping their son out of the spotlight has helped their family grow together: “It was important to us to choose how to share him with the world because this is a whole new era for me. It’s no longer just about me. I have a wife, a child – a family. It’s terrifying. It’s invigorating. It’s more meaningful than anything I’ve ever been part of.”
“Can’t Stop the Feeling” was written for – and because of – Silas.
The feel-good tune was something Timberlake knew he wanted in his catalog when he set out to write the Trolls smash hit. He was looking for the kind of summertime anthem he enjoyed as a kid, but his son also helped him bring the idea to fruition: "When I first saw my son, I had such intense feelings – nothing that I’ve ever experienced can compare to it. I could have never written ‘Can’t Stop the Feeling’ without knowing my son. If you want to know how I felt when I first saw Silas, listen to ‘Can’t Stop the Feeling.’”
“Say Something” is just one of many songs he and Chris Stapleton have written together.
Though their mutual admiration society is hardly a secret one, Timberlake spends two pages gushing over Stapleton's musical genius and what the country star brought to Man of the Woods. Stapleton is only featured on one MOTW track, but Timberlake hints that it may not be the only JT/Stapleton collab in existence: "We wrote many more songs together that are sitting in the vault somewhere. Maybe they’ll see the light of day someday.”