Serious Question: When was Peak Justin Timberlake?

Serious Question is when we pose a question and then try to answer it. Usually the question is not very serious.
Few things have a 100-percent approval rating. This is another way of saying that few things are truly universally beloved. Grilled cheese sandwiches are universally beloved. So are fat NFL players doing touchdown dances. So is March of the Penguins. Figuring out which things are universally beloved is hard even though the answers feel obvious.
I was having a rabbit-hole conversation with some friends the other day when we went from talking about movie trailers to all-time-great movie trailers to The Social Network to Justin Timberlake. Someone said it might be Justin Timberlake’s finest hour. Someone else said, no way, that was “SexyBack.” Someone else said it was his Lonely Island appearances. We all told that person that they were wrong, but regardless, the topic went unsettled. When is Justin Timberlake’s peak? Is it over? Is he in it right now? It’s certainly something worth examining in too much detail.
It seemed reasonable to begin this exploration by talking about 100-percent approval ratings because, ultimately, that’s how we can determine the arrival of Peak Justin Timberlake. JT is already a popular public figure, but he probably has a few detractors. Well, that can’t have always been the case. There had to be one cultural moment where Justin Timberlake was so undeniably excellent that the people who didn’t like him came aboard and the people who did like him stuck around. That moment is when Justin Timberlake had a 100-percent approval rating. That moment is when we were blessed with Peak JT.
Of course, it would be silly (and foolish, really) to examine every second of JT’s career, so for the sake of our study, let’s only focus on the absolute high notes of this timeline. That gives us the easiest potential pathway to Peak JT. Now, without question, the first high note is:
Tearin’ Up My Heart (1997)
Early NSYNC is curious. They’re big in Germany at least 18 months before they’re big in America, and throughout their Euro-centric stretch of popularity it’s evident that they don’t really know how to present themselves as a group. The “Tearin’ Up My Heart” video presents this dynamic well—no one really hogs the screen, and the video is really careful to make everything fair. Sometimes Justin is in the front. Sometimes he’s in the back. Sometimes he’s in the middle. Sometimes he’s off to the side. The same goes for the other group members, and while the song is a solid boy-band-era staple and the video is chock full of wonderful late-90s tropes (everyone really loved billowing white shirts, didn’t they?), it means our guy JT isn’t at 100-percent approval yet. In fact, he wasn’t even everyone’s favorite NSYNC member yet (Lance might have come closest—he was “The Hot One” at first).
Approval Rating: 74/100
Bye Bye Bye (2000)
Case closed, you say. This is it. NSYNC was never better (true) and JT was never better in NSYNC (false). The case for Justin here is really strong, especially with the video—he earns the right to sing the bridge all by himself, he summersaults through the narrative scenes, he does this zippy little pelvic thrust—it’s great. The group finally seems like they’ve realized how talented JT is, but at the same time, they don’t go all-in. He takes the second verse instead of the first, and in the most important dance scenes other members are leading the fist-pumps and hand-waves. It’s really too bad. Plus, Justin was in the heart of the frosted-tips craze, and while it wasn’t the worst look in NSYNC (shoutout Joey Fatone and his red tips!), it wasn’t the best either (sup, JC). Some people definitely disapproved.
Approval Rating: 83/100
It’s Gonna Be Me (2000)
This song is as good as Justin ever was with NSYNC. He is unquestionably the frontman and figurehead of the group. He scores all the immortal lines and runs and dance moves and it’s the point when we all had to stop pretending to like any other NSYNC member as much as him. So this is when he had a 100-percent approval rating, right? Nope. Because you know who’s still messing around in Orlando, moving records like literally no one ever has before?
Yep, as long as the Backstreet Boys were in their prime, there were going to be people who were out on Justin for the sole reason of him being in NSYNC. Sorry, but people are petty and the world is unfair.
Approval Rating: 97/100
Cry Me A River (2002)
What about “Pop,” you ask? We’re skipping over it. It’s clearly not Peak JT. Sure, it was one of our first looks at super-short-hair JT, and we even have one of our first instances of JT doing that thing where he beatboxes at the end of songs (he would do it all over Justified and FutureSex/LoveSounds), but when “Pop” came out in 2001, NSYNC was past their prime and people were generally out on boy bands. A 100-percent approval rating is unlikely.
Justified, JT’s inevitable first solo album, comes out in 2002, and while it’s not the revelation we probably wish it was, it did provide “Cry Me A River,” which is no-joke one of the great cultural moments of the early 2000s. It’s perfect. JT is perfect on it. He’s perfect in the video and perfect on the record and the whole narrative surrounding the song is a terrific microcosm of that time in music. Let’s break it down.
As a song, “Cry Me A River” is hard to argue against. JT shows terrific range, the instrumental is appropriately slinky and sly, and man, you can just feel all the pettiness and regret and want and bitterness. The video, too, is great for how ballsy it is. JT smirks and sneers and somehow comes across as the most understandable douchebag imaginable. JT films himself macking on a chick with a tramp-stamp in this video and he comes out clean. Truly an accomplishment.
“Cry Me A River” announced Justin Timberlake as a legitimate solo artist—a guy with talent, charisma, creativity, and a finger on the pulse of cultural conversation. It’s awesome, but he doesn’t earn 100-percent approval, because by nature of making a diss track against Britney Spears, you’re going to see some Britney Spears defenders come out of the woodwork (she hadn’t fallen off the cliff yet, by the way—her response to “Cry Me A River” would be the ballad “Everytime”).
Approval Rating: 98/100
Timbaland’s Approval Rating: 100/100*
*Timbaland not only produced “Cry Me A River,” but also scored the best role in the video. He’s JT’s getaway driver, and he spends a lot of his screentime rubbing his hands together gleefully. Everyone loved Timbaland after that.
Punk’d (2002)
Any time Ashton Kutcher makes you cry, we have to question your strength as a person. You have to dig deep into the MTV website to find footage of it (you're welcome), but it's not hard to see: This might be JT’s rock bottom.
Approval Rating: 61/100
The Janet Jackson Wardrobe Malfunction (2004)
Something I still find remarkable about this incident is how Justin Timberlake emerged as clean as he did. While I was researching this article, I called my mom and asked her what she remembered about the incident. I expected her to scorn JT, but instead, she said, “I don’t think I thought much about him at all. That was all about Janet Jackson. No one really cared about him.” JT handled this so deftly that my own mother doesn’t blame him one iota to this day. He’s somehow trending up.
Approval Rating: 70/100
SexyBack (2006)
Nevertheless, in the wake of pulling off Janet Jackson’s top, JT did some aimless soul-searching. He acted in some small-time movies. He ventured into the recording artist’s Heart of Darkness (which is to say he recorded some songs with the Black Eyed Peas). He had some nodules surgically removed from his throat in 2005. It seemed likely at the time that Peak Justin Timberlake was in the past, but in 2006, the world was blind-sided by his second solo album, and no one was ready for JT’s second solo album.
FutureSex/LoveSounds, and its lead single “SexyBack,” are revelations in a literal sense. We had no idea Justin Timberlake could be this good at anything, let alone create music this fun, this diverse, this badass. It would be selling “SexyBack” short to say that it announced the rebirth of JT, because the JT we have on the “SexyBack” record and FutureSex/LoveSounds as a whole is not the same JT who gave us “It’s Gonna Be Me” or even “Cry Me A River.” That JT was a staple of pop music, but in 2006 he evolved into a figure who dominated pop music. FutureSex/LoveSounds is like if you took a Prince album, threw it in a Timberlake blast chiller, topped it with some Bowie-injected glamour and served it on a copy of Thriller. It sounds like all of these things but is also entirely its own.
Does anyone dislike “SexyBack?” That’s the final, inevitable question here, right? The record was JT’s first Billboard No. 1 as a solo artist, Timbaland’s production job is eternal (as are his backup lines), and the video is suitably chilly and provocative. On top of it all, JT is golden here. He’s seductive and submissive and commanding and controlled, and there’s not a single point in the song when you’re thinking, “Eh, actually, can sexy stay where it is?” Nope. You want sexy to come back and you want JT to deliver it. It’s the greatest. It makes you feel like you’re the greatest, even though you know that Justin Timberlake is actually the greatest. Do you understand why you and I and my mother don’t care about JT’s involvement in that Super Bowl halftime show? Because “SexyBack” came out. It’s in this moment when JT finally won. He won every single one of us.
Approval Rating: 100/100—PEAK JUSTIN TIMBERLAKE
Epilogue: The Social Network, Etc.
It’s hard to say if we’re still in the midst of Peak Justin Timberlake. Probably not, though to the man’s credit, he’s remarkably still evolving as a performer and musician. In the wake of FutureSex/LoveSounds’ meteor impact, another musical hiatus gave us collaborations with Madonna (remember when “4 Minutes” was everywhere?) and 50 Cent before JT jumped back into acting. He floundered for a bit, but then in 2010 some apparent geniuses attached him to The Social Network.
For better or for worse, Justin Timberlake’s portrayal of Sean Parker in The Social Network is still the cultural artifact that has us convinced JT can be a great actor. He’s awesome in the movie—grand, cocky, douchey, charming, sharp—everything we thought about Justin Timberlake, really. It doesn’t hurt either that he scores one of the movie’s more memorable lines. (“A million dollars isn’t cool. You know what’s cool? A billion dollars.”)
In 2013, JT treats us to the sweeping ambition of The 20/20 Experience (in two parts!), and while it lacks a truly permanent single, it has surprising legs and replay value. With its eight-minute tracks and bigger club-to-concert-hall instrumentation, it instituted the arrival of Distinguished Timberlake, and while that didn’t carry the shock and awe of Dangerous Timberlake in 2006, it’s hard to speak negatively about the career turn. Even if “Mirrors” and “Can’t Stop the Feeling!” aren’t quite Peak Justin Timberlake, they would be the peak of 95-percent of other artists. This Justin Timberlake, with his snappy bow ties and white jackets and harmless (but infectious) summer jams, might not soak the club and go home with your girlfriend, but he will throw one hell of a gala event. And that’s okay—JT is only 35. He’s given himself time to peak again.