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Usher’s Funniest, Freakiest Cherry-Feeding Concert Serenade Moments

From Keke Palmer's infamous night to the steamy Chicago woman, get ready to clutch your pearls at how Usher continues to make women everywhere hot and bothered!

Photo: Getty Images Kevin Mazur/MG25

Usher has long been the “King of R&B” and the object of desire for women almost everywhere for decades, but his Las Vegas residency and recent tour have elevated him to legendary status. Thanks to his steamy serenades and sensual cherry feedings specifically, the “There Goes My Baby” performer’s shows have become a masterclass in flirtatious showmanship.

Whether he’s getting hot and heavy with a fan or giving a sultry serenade to a fellow celeb, these hilarious and often pearl clutching interactions have become viral sensations. (And if we’re honest, it makes us a little jealous. We like cherries too, Usher!!)

Considering that he just wrapped his “Past, Present, Future” tour, we thought it’d be fun to take a look back at some of his most memorable, “cherry” moments and serenades. From Keke Palmer’s controversial appearance to Sabrina Carpenter’s Met Gala cherry tease, let these fun times remind you why we’ll forever call him Mr. U-S-H-E-R R-A-Y-M-O-N-D.

Keep reading to get into the goodness!

Usher and Sabrina Carpenter

@yazzyrogers

Usher Picks Sabrina Carpenter As Cherry Girl At Met Gala Performance! Have you ever tried this one? #popculturenews #metgala #sabrinacarpenter #usher #tour #surprise #performance #cherry #celebritynews #usherpastpresentfuturetour #juno #junoposition #themet #2025 #shortnsweet #sabrinacarpenteredit #greenscreen

♬ original sound – Yaz

Just because Usher’s tour is over doesn’t mean he has to stop doing what he does best: making ladies go wild and feeding them sweet treats. And that’s exactly what happened at this year’s Met Gala, but pop singer Sabrina Carpenter (who’s been known to pull a few sensual moves herself ) arguably had the best night of all.

Usher and Keke Palmer

Now, while Keke Palmer’s serenade happened sans cherries, we had to include it for the myriad of think pieces, tweets, posts, songs and interviews it spawned. Who knew getting sweet nothings sung to you by Usher would cause all this commotion??

Usher and the Sexy, “Married” Woman from Chicago

@monochromeego

I was second hand shy. aunty knew what she came for! #usher #usherday3

♬ original sound – 💕 JOANITA. 💕

You already know this was going to be in our top five because if we’re honest: we’re still trying to wipe the sweat from our forehead after being witnesses to this moment. Shoutout to you, Jimalita Tillman…you were honestly the real star of this show!

Usher and the Beauty Influencer

@estare

Wait, this really happened?!! 🥹🤤 Thank you @sofiia #usherconcert #ushercherry

♬ original sound – estare

Digital creator Estare understood the assignment exactly when Usher came over to the U.K. to feed his London fans. Not only did she seductively receive Usher, she matched his energy and tried to offer it back to him.

That’s what we’re talking about, give us a REAL SHOW!

Usher and Halle Bailey…Kinda

The more we look back at this footage, the more it only appears to be a subtle foreshadowing of some possible deeper issues, but at least Usher and Halle were good sports about it!

Usher and Tiny

While we all know how protective rapper T.I. is about his wife Tiny, it was fun to see him just relax and let his wife enjoy the moment. All’s fair in love and cherries, right?

Usher and Sabrina Elba…Kinda

Once again, Usher played it safe when Idris Elba and his wife Sabrina decided to show up to one of his U.K. shows. Even though the “Hobbs and Shaw” star fed the cherry to his own partner, you’ve got to give Usher props for the assist!

Usher and the “Plus-Sized” Model

@therealgraciebon

so happy 🍒 thank you @Usher Raymond

♬ hey daddy – usher

Though there was nothing inherently different about Usher feeding this fan a cherry, folks online had plenty of things to say about this “plus-sized” model’s interaction.

Usher and the Black Woman from Amsterdam

The most hilarious part of this entire moment is that, for once, we couldn’t tell if Usher was impressed or genuinely confused at the vibe he was getting from this fan. All we know is that his reaction was priceless.

Usher and the “Minor”

Not every cherry moment goes off without a hitch, and that’s exactly what happened during one of Usher’s U.K. tour stops when he thought a fan may have been a bit too young to be there — and definitely too young to partake in some sensual cherry activities.

Usher and Issa Rae

Much like Keke Palmer, this moment between Usher and Issa Rae happened before the cherries were introduced into the fold. But there was just something about seeing someone like Issa (who feels like our homegirl) get to have this sexy, cool moment with a literal superstar that just felt like a win for all of the girlies!

Usher and an Eager to Please Fan

Sure, we’re all adults here and there’s a clear sexual reference happening here but for once, it may have taken Usher aback. (And us too, if we’re honest!)

Honorable Mention: Usher Being Absolutely Over It

@morganrachan

POV: When Usher’s cherry-feeding segment takes an unexpected turn, and his face says it all 😂🍒 #UsherConcert #CherryMoment #fyp #atlanta #atl #usher #pastpresentfuturetour

♬ WHATCHU KNO ABOUT ME – GloRilla & Sexyy Red

In a moment that can only be described as “let me get my ass on up out of here,” Usher was clearly making a beeline towards the exit after a fan got a bit carried away with his cherries. Once again, the King of R&B became the king of memes because his face is a whole mood!

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