Justin Timberlake’s Career in Memes, From ‘It’s Gonna Be May’ to His DWI Mugshot

It’s always a cultural event when a celebrity is arrested, but often enough, people are willing to forgive someone who has starred in great movies, dazzled as a pro athlete, or recorded favorite hit singles. Justin Timberlake, however, can no longer trade on his history with ‘NSync or his peak as a solo artist to stay in the public’s good graces: when he was arrested and charged with driving while intoxicated in the Hamptons early on Tuesday morning, the resounding consensus on social media was that he deserved the embarrassment.

Why? Chalk it up to a very bad track record with women. In recent years, commentators have reevaluated the infamous “Nipplegate” scandal at the Super Bowl halftime show in 2004, when Janet Jackson took the fall for a “wardrobe malfunction,” while Timberlake, who had ripped off part of her costume and exposed her breast, kept his career more or less on track. Last year, Britney Spears‘ memoir The Woman in Me leveled the accusation that Timberlake had cheated on her when they dated, after Timberlake famously released a song after the breakup implying that she had been unfaithful. (Headlines about infidelities have also dogged his relationship with now-wife Jessica Biel, though he has denied them.)

While the turn of the tide against Timberlake may seem sudden, you can actually track his slide from “Prince of Pop” to persona non grata through the 21st-century language of the masses — that being memes. Here, take a stroll through the past decade or so of viral Timberlake content:

It’s Gonna Be May

As far back as 2012, Tumblr users were joking about Timberlake’s vocals on the 2000 single “It’s Gonna Be Me,” from ‘NSync’s second album, No Strings Attached. When Timberlake sings the title of the song, he emphasizes the word “me” so that it sounds more like “may.” Therefore, around the end of April, you could post an image of Timberlake with the text “It’s Gonna Be May” to announce the upcoming month. This was the kind of lighthearted, Impact-font image macro that made sense in a more innocent time, when Barack Obama was cruising to reelection (his comms team got in on the joke in 2014) and Timberlake wasn’t “problematic” or “canceled” — terms not yet endemic to social media. It was a bit of premature Y2K nostalgia based around a familiar face and a misheard lyric, the kind of positive PR that you simply can’t buy. That this meme was nowhere to be found the past few springs tells you how hard Timberlake has fallen off.

Man of the Woods

In 2018, Timberlake released his first album in five years, following the back-to-back platinum 20/20 Experience records of 2013. He signaled that this new release, Man of the Woods, would be a major departure from his club-friendly sound, playing on his Memphis roots as he explored blues and country. The pivot prompted surprise and sarcasm among listeners who smelled a cheap rebrand after a hiatus Timberlake partially spent producing the soundtrack for Trolls, and his newfound lumberjack aesthetic launched a million jabs about trying to have a Mumford & Sons era. The headlines were brutal, not least because Timberlake had also appeared in the 2017 Woody Allen movie Wonder Wheel, which premiered as the #MeToo movement took off. Man of the Woods debuted at number one, and it still went platinum — but that took three years. Clearly, he was already beginning to trend downward.

Super Bowl Selfie Kid

The week Man of the Woods came out, Timberlake headlined the halftime show for Super Bow LII, which may have helped sales, but reminded everyone that Janet Jackson had vanished from the spotlight after their ill-fated 2004 performance ushered in a wave of misogyny and puritanical outrage. Luckily for him, a spontaneous interaction with a kid in the crowd proved to be the winning viral moment of the show. Timberlake posed with seventh-grader Ryan McKenna as he took a selfie of them together, though it was McKenna appearing somewhat flustered and looking down at his phone after the singer moved on that drew the most attention. A plurality of the memes suggested that the youth didn’t care about or recognize Timberlake, and may have been Googling who he was. Timberlake made the most of the encounter by calling in to chat when McKenna gave an interview on The Ellen DeGeneres Show, yet the writing on the wall about his fading relevance was legible.

Drop the [Blank]. It’s Cleaner

The Social Network (2010) is surely the best film Timberlake has ever done. Nevertheless, it’s a little confusing that one of his most memorable lines didn’t really take off as an exploitable template for another 10 years or so. In the scene, Timberlake, as wily Napster co-founder Sean Parker, advises future Facebook billionaire Mark Zuckerberg (Jesse Eisenberg) to tweak the name of the website: “Drop the ‘the.’ Just ‘Facebook.’ It’s cleaner.” Zuck marvels at the branding genius of the man who will go on to briefly serve as president of the social media company and acquire his own hefty stake in it. In the online remixes, though, Parker’s ideas appear to be the self-evidently stupid, shallow epiphanies of an arrogant dweeb with nothing much to contribute, hinting at how we came to identify Timberlake with opportunist gimmickry. It even came full-circle with Facebook’s widely mocked shift to “Meta.” Had Timberlake’s acting career survived, this wouldn’t be such a damning association. Instead, it’s a defining one.

Beat Ya Feet

After performing at Pharrell Williams‘ “Something in the Water” music festival in the summer of 2022, Timberlake was forced to do what no entertainer ever wants to: apologize to an entire city. His faux pas, as it were, was an attempted tribute to Washington, D.C.’s celebrated go-go music, and a dance style born out of its bouncy funk rhythms — Beat Ya Feet. Alas, Timberlake’s stilted interpretation of the moves caused grievous offense and left some wondering just when he’d gotten so cringe. The footwork was roasted as everything from Riverdance to the Hokey Pokey to the “Silver Spring Shuffle,” and Timberlake’s Instagram Story response, in which he jokingly blamed the khakis he wore for the show, didn’t endear him to those inclined to see him as all washed up. The cool factor he enjoyed in the early 2010s had obviously expired.

Arrest, Mugshot, and World Tour Slight

By the time Timberlake got pulled over this week, the fix was in. Critics were underwhelmed by his sixth studio album, Everything I Thought It Was, released in April, and the music did nothing to halt the souring of his reputation, wildly accelerated by Spears’ candid recollections of their time together in her book. Timberlake seemed to acknowledge, too, the impact that his arrest would have on the world tour he began two months ago in Vancouver, telling an officer too young to recognize him (another humiliation) that it would “ruin” his concert schedule. (“What tour?” “The wold tour” will go down in history as one of the harshest accidental burns of all time.) Hardly anyone observed the incident on social media without reveling in his misery, speculating that he danced during field sobriety tests, or marveling at the quality of his mugshot. These comments were met by an avalanche of claims that this was karmic comeuppance for a track record of bad behavior. In the end, Timberlake had no one to defend him, which is a tough place to be in for someone who makes a living off their popularity. If he wants redemption, he has quite the hill to climb.