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Let’s talk about the 2025 Grammy Awards, because oh boy, did we get some unforgettable moments – and not always for the right reasons!
While the show faced some serious challenges, taking place just weeks after devastating fires rocked Los Angeles, the Recording Academy managed to pull together a night of stellar performances and touching tributes.
But you know how it goes with these star-studded events – there’s bound to be some awkward moments that make you want to hide behind your couch cushions. From fashion fails to foot-in-mouth moments, here are the five most cringe-worthy incidents that had us all collectively gasping, ranked from “Okay, that’s kind of awkward” to “Did that really just happen?”
5Jaden Smith’s architectural fashion statement
Just when you think you’ve seen it all on a Grammy red carpet,Jaden Smithshows up wearing… wait for it… an actual castle on his head! No, this isn’t a metaphor or an exaggeration – we’re talking about a legitimate, black, castle-shaped structure with a face-hole cut out of it. Picture the most extra Medieval Times souvenir you can imagine, then make it fashion.
The “Summertime in Paris” singer strolled down the red carpet like it was the most normal thing in the world to be wearing architecture as an accessory, while his sisterWILLOWwalked beside him, presumably pretending this was totally fine.
Jaden smith arrives at the#Grammywith a spectacular outfitpic.twitter.com/cjo0pvLiDo
The headpiece, created by Transylvanian designer Dora Abodi, had everyone doing double-takes and probably wondering if they’d accidentally tuned into a costume party instead of the Grammys. The real kicker? Smith paired this over-the-top headpiece with a completely classic black suit, creating a contrast so stark it was like wearing flip-flops with a tuxedo.
It’s the kind of fashion moment that makes you wonder if he lost a bet or if this is just what happens when you let your Minecraft obsession influence your wardrobe choices.
4Lainey Wilson’s awkward tribute performance
If there was ever a textbook example of “wrong place, wrong time,” Lainey Wilson’s performance in theQuincy Jonestribute segment would be it. Picture this:Cynthia Erivojust finished absolutely slaying “Fly Me to the Moon” – we’re talking goosebumps-inducing perfection here. Then, poor Lainey Wilson steps up to perform “Let the Good Times Roll,” and what follows can only be described as a country music stereotype come to life.
A post shared by Live Nation Concerts (@livenation)
Don’t take it the wrong way, Wilson’s got serious pipes – that final note was absolutely killer! But everything else? It was like watching someone play “country singer” in a high school musical.
The fringed leather pants and cowboy hat combo felt more like a costume than an outfit, and her accent was cranked up to eleven, making it nearly impossible to understand the lyrics. Sure, country music is having its moment again, but this performance felt like it was trying way too hard to remind us of that fact. Even the most die-hard country fans were probably reaching for the remote.
3Trevor Noah’s tone-deaf Colombia joke
You know that moment when a joke falls so flat it practically burrows into the ground? That’s exactly what happened duringTrevor Noah‘s opening monologue. The host, who’s usually pretty sharp with his comedy, really missed the mark when he decided to crack wise about Colombia while introducingShakira.
Three-time Grammy winner Shakira is in the house. The greatest thing out of Colombia that isn’t a felony,
he quipped, and yikes – you could practically hear the audience’s uncomfortable shuffle.
Doechii rolls her eyes at Trevor Noah’s Immigration joke#GRAMMYs📹 .@El_Poojypic.twitter.com/qNBt29YnCG
What makes this particularly face-palm worthy is that Noah had actually landed some solid political jabs earlier, including some clever hits aboutDonald Trump‘s Canadian tariffs.
But instead of sticking with current events, he went for this dated stereotype that felt especially tone-deaf given the ongoing challenges faced by Latino immigrants in the U.S. It’s like bringing a dad joke to a comedy club – sometimes the classics are better left in the past, don’t you think?
2AP reporters’ disrespectful treatment of Babyface
Picture this: you’re watching the red carpet coverage, and there’s the legendary Babyface – you know, just the guy who’s shaped modern R&B and has enough Grammys to fill a small trophy case – sharing what’s probably some incredible industry insights.
But wait! What’s that? The AP (Associated Press) reporters just spotted rising starChappell Roanwalking by, and suddenly, it’s like Babyface might as well be invisible.
“This was really disrespectful”: Babyface Getting Ignored Because of Chappell Roan on Grammys Red Carpet Is Just Painful to Watch
The reporters actuallycut off the music legend mid-sentence, practically snatching the mic away while fumbling through apologies to chase down the “Hot To Go” singer. Talk about a major faux pas! But Babyface still handled it with total class, which somehow made the whole thing even more cringe-worthy. Social media absolutely exploded with fans calling out this display of disrespect, and honestly, can you blame them?
1Kanye West and Bianca Censori’s shocking exit
Hold onto your seats, because this is where the Grammy Awards went from “Oh, that’s awkward” to “Is this actually happening?”Kanye West, making his first Grammy appearance in ten years, decided to make it memorable – and boy, did he succeed! The rapper and his wifeBianca Censoriturned the red carpet into their personal shock-value showcase, with a stunt that had jaws dropping and security guards moving.
Bianca Censori Beats Kim Kardashian With Her Grammy Outfit: Jennifer Lopez Doesn’t Top the Most Revealing Grammy Dresses List Anymore
Picture this: they arrive, Censori wearing what appeared to be a perfectly normal oversized black fur coat. Then, in a move that nobody asked for but everybody witnessed, she dramatically dropped the coat to reveal… well, basically nothing.
We’re talking about a dress so sheer it might as well have been made of wishful thinking, crafted from what looked like stockings and paired with clear heels because why not go all in?According to Page Six, the couple was apparently trying to recreate West’sVultures 1album cover, but what they actually created was their own exit from the ceremony.
A post shared by Vanity Fair (@vanityfair)
The duo, who tied the knot in 2022, didn’t even get to stick around to see if West would win his 25th Grammy for “Carnival” (spoiler alert: he didn’t –Kendrick Lamar‘s “Not Like Us” took home the gold). Instead, they were escorted out and spotted leaving in a silver chrome car, proving that sometimes the most memorable Grammy moments happen before the show even really begins.
These eye-popping incidents prove that even music’s biggest night can’t escape those moments that make you want to watch through your fingers. While the 2025 Grammy Awards delivered plenty of amazing performances and well-deserved wins, these cringe-worthy moments definitely gave us something to talk about around the water cooler. Hey, at least no one interrupted anyone’s acceptance speech this year, right?
Sweta Rath
Articles Published :269
Sweta Rath is an Author at FandomWire, specializing in long-form articles, explainers, and entertainment analysis covering movies, TV series, and celebrity profiles. A results-driven content strategist, she combines analytical precision with creative storytelling to deliver authoritative entertainment content.Her diverse skill set includes SEO optimization, digital marketing, and WordPress content management, enabling her to create high-performing content that bridges scholarly literary insight with accessible fan engagement across multiple digital platforms.
