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Usher’s 50 Best Songs: Staff Picks

Written by on February 7, 2024

Before the pop and R&B legend takes the world’s biggest stage this weekend, a look back at the songs that have defined his generational hitmaking career up to this point.

It was always going to happen. Maybe not the Super Bowl gig necessarily — only so many folks get to do that, and things have to break just the right way for it to even be an option — but the general Usherssaince of 2024, where Mr. Raymond once again finds himself among the most vital and celebrated performers in pop and R&B.

Was he ever really gone? Not really, but also kinda — at least more than he ever should have been. From 2017 to 2022, Usher only reached the Billboard Hot 100 three times, never as a solo lead, and never higher than No. 40. For Usher’s last visit of any kind to the chart’s top 10, we have to go back over a decade, to the No. 9-peaking “Scream” in 2012. And it wasn’t just that one chart: His R&B radio success became erratic, his touring level declined from arenas to theaters and his media coverage started focusing less on his new releases and more on his scandals, lawsuits and Usher Bucks.

Some of this might have been inevitable for any superstar in his late 30s and early 40s while in the third decade of his recording career. But Usher isn’t just any superstar: He’s a singular artist who’s had a generational career. He’s had era-defining singles in at least three different top 40 eras. He’s spent a year as the greatest pop star in the world. He want Diamond on sales alone, for an album released a half-decade after Napster’s debut. He has the best friend-crush song of the ’90s, the best cheating song of the ’00s and the best breakup song of the ’10s. He has the greatest singer-playing-themselves film cameo of all time. And though he may have put his superstardom on pause, he never stopped being great: The last 10 years of his career have featured several of his finest singles and most rewarding deep cuts yet. Early-pandemic social media talk theorizing about him battling Justin Timberlake or Chris Brown in a prospective Verzuz was always misguided; when thinking Usher peers, think Beyoncé.

And whether or not he was truly gone, he is now undeniably back. Not only is Usher on the cover of Billboard today, and not only is he headlining the most-watched gig in the world this weekend, but he’s releasing his first proper solo album (Coming Home) in eight years on Friday — and it already has his biggest hit in even longer than that, with the Summer Walker and 21 Savage collab “Good Good.” Plus, after a successful Vegas residency revived his live fortunes earlier this decade, he’ll be heading back out on an arena tour starting this summer — bringing one of the greatest artists of the modern pop era back to the venues where he belongs.

Before all that, though, we wanted to recap the Best of Usher so far: Our staff’s picks for the 50 best songs from the man they call Ursher, baby through his first three decades. We can’t wait for the fourth to get going.

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