I’ve become a big fan of Stereogum’s series The Number Ones, in which Tom Breihan discusses every song that’s hit #1 on the Billboard Hot 100. It’s a fascinating list, full of songs I completely forgot about or never knew existed, mind-boggling omissions (Missy Elliott has never had a solo #1; “Since You’ve Been Gone” peaked at #2), and a dawning realization that I have never been in touch with this metric of musical success. But I do generally understand the numbers you need to have a hit record. And they have to be higher than 67,000, which is how many units of Justin Timberlake’s latest album moved in its first week. And definitely higher than 14,000, the numbers for Jennifer Lopez’s latest. As the girl from the block said herself, “it’s not like anyone was clamoring for the next J.Lo record.”
It’s been captivating to watch these two superstars, who have been massively famous for more than half of my life, absolutely face-plant while using the same nostalgic comeback playbook.
I imagine this makes about as much sense to Gen Z/Alpha as my mom saying this about Donny Osmond 25 years ago did to me, but: before the animated movie soundtracks, Justin Timberlake used to be a fucking cool sex symbol. We liked him, like a lot. We liked him when he was with Britney. We liked him even more after their break-up. We liked that Michael Jackson liked him enough to give him some of his cast-off songs. We liked that he worked with Pharrell and Timbaland and David Fincher. We liked that he would show up on SNL being legitimately funny, and we liked that he was friends with Jimmy Fallon (who we also used to like!) and Andy Samberg. And I can hear some of y’all exhaling out your nose and saying “not me though,” and that’s fine. Congrats on always having impeccably moral taste. But statistically speaking, yes you though.

So when did things start to turn for Justin? Allegations about him stepping out on his wife got louder, but they seemed to navigate that the way most straight couples in the public eye do (“ups and downs,” “disrespect,” “my best friend,” “stronger than ever”). Everyone seemed to hate his 2018 album Man of the Woods, but it still sold 293,000 albums in its first week, and bad music alone rarely sinks a star’s career.
But the one-two punch of Janet Jackson’s 2022 documentary, which gave us very little new information but did have Janet being a serene, soft-spoken martyr at its center; and the cascading revelations about his relationship with Britney Spears, is what really sank him. Had it just been the Janet documentary, he may have survived. Partly because the facts of the case were already a matter of very public record. We already knew that he accidentally exposed Janet’s breast during the Super Bowl XXXVIII Halftime Show and paid absolutely nothing for it while Janet’s career got completely railroaded. This wasn’t news. And partly because the same forces at play in 2004—his whiteness and maleness, her Blackness and femaleness—are still at play. This is still a racist patriarchy that wants to forgive a white man for behavior that it wants to write off as simply mischievous. But his offenses are stickier now than they were, and his Teflon was wearing thin. Combine that with our newfound protectiveness of Britney Spears, borne out of our collective guilt about making her into a spectacle when she was extremely vulnerable, and Justin became a villain.
By the time he realized he should finally mend fences with the rest of NSYNC and earn back a little goodwill, the chance for nostalgia-based redemption had passed. So now, Justin can do his little Tiny Desk Concert, but it better all be FutureSex/LoveSounds and maybe that one Trolls song. We don’t want to hear anything new from this man anymore. We don’t want to see him beat his feet in some Dockers. We don’t want it.
J.Lo’s comeback approach has been similar, though the energy has been different. After the crushing blow of getting zero Oscar nominations for her legitimately great Hustlers performance, Jenny went back to the wedding movie industrial complex that has been her bread & butter for almost 25 years. And she went back to the relationship that terrorized newsstands 20 years earlier, even going so far as to recreate scenes from her “Jenny from the Block” music video for the paparazzi. I’d say the fever pitch about Bennifer: Back in the Habit reached 2003 heights, but with the softening effect of nostalgia taking some of the meanness out of things. This star-crossed Leo pair gives great pap shots, separately and together, and we ate the whole thing up. Everything felt very familiar, if not necessarily good.
But somewhere around their second Dunkin commercial, things started getting weird. Like, heart factory dream weird.
Jennifer poured her HEART SOUL DREAMS into a visual album about her obsessive search for love. And while plenty of us tuned in to watch the spectacle, none of us bought or streamed the album itself. None of us bought tickets to her comeback tour. We’ve internalized too much about how little of J.Lo’s voice, and how much of Black women’s voices, figure into her most iconic riffs. We can’t get excited about her new music. We don’t want it.
That’s why I feel like nostalgia bait only goes so far. These entertainers who became celebrities 30 years ago can trigger some dusty affection in us by reminding us how they made us feel back then, and how much younger we were back then. But they can’t make us retain the cultural values we had back then, or make us forget everything we’ve learned since then. We’re judging them with 2024 values and knowledge, and finding them wanting. They still have their fans, and their wealth. But they don’t have their relevance, or the benefit of the doubt. And even the low-level schadenfreude that comes from watching someone become a villain, and then a flop, can’t truly extend their shelf life.