15 Awkward Moments from the 2025 Grammys That Had Everyone Cringing—You Won’t Believe #7!

The 2025 Gram­my Awards were noth­ing short of spec­tac­u­lar, with daz­zling per­for­mances, emo­tion­al speech­es, and plen­ty of fash­ion moments that had every­one talk­ing. How­ev­er, it wasn’t just the flaw­less moments that cap­tured the atten­tion of viewers—this year’s cer­e­mo­ny was filled with awk­ward, cringe-wor­thy inci­dents that left fans in shock and made head­lines for all the wrong rea­sons.

From mis­pro­nun­ci­a­tions and snubs to ques­tion­able fash­ion choic­es and con­tro­ver­sial state­ments, the 2025 Gram­mys were marked by a series of uncom­fort­able encoun­ters. In this arti­cle, we’ll take a deep dive into 15 of the most unfor­get­table, and painful­ly awk­ward, moments that left the audi­ence gasp­ing.

1. Kendrick Lamar Seems To Say “Drake, What’s Up?”

The ten­sion between Kendrick Lamar and Drake has been a long-stand­ing top­ic in the music indus­try, with fans and media often spec­u­lat­ing about the nature of their rela­tion­ship. So, when Kendrick Lamar took the stage at the 2025 Gram­mys to accept his Record of the Year award, every­one was on high alert, wait­ing for what he might say.

As he deliv­ered his accep­tance speech, Lamar’s greet­ing sound­ed almost like a jab at Drake. “Drake, what’s up?” he said, leav­ing fans on edge. But, much to the relief of those hop­ing for peace, Kendrick actu­al­ly said “Dre, what’s up?” refer­ring to the leg­endary Dr. Dre, not his Cana­di­an rival. It was an awk­ward moment for Drake fans who had been eager­ly watch­ing, but Lamar’s casu­al com­ment turned out to be harm­less.

Kendrick Lamar takes home Song of the Year for “NOT LIKE US” – watch his pow­er­ful 2025 GRAM­MYs accep­tance speech!

2. Chappell Roan Calls Out Music Labels

In an unex­pect­ed moment of raw hon­esty, Chap­pell Roan used her Gram­my accep­tance speech to call out the music indus­try for its treat­ment of artists. As she stood before the most pow­er­ful fig­ures in music, Roan pas­sion­ate­ly spoke out about being “betrayed” by the sys­tem. She revealed that, after being signed to a label as a minor, she was dropped with­out warn­ing and left with­out a job or the means to secure insur­ance dur­ing the pan­dem­ic.

Her com­ments, “Labels, we got you, but do you got us?” res­onat­ed with many, spark­ing a debate on social media about the eth­i­cal treat­ment of musi­cians. While some appre­ci­at­ed her courage to speak up, oth­ers crit­i­cized her for what they saw as com­plain­ing. Roan’s bold speech high­light­ed a major issue in the music indus­try, but it also made for a rather uncom­fort­able moment for the audi­ence.

3. Taylor Swift and Cynthia Erivo’s “Holding Space” Meme Moment

When actress Cyn­thia Eri­vo was hav­ing dif­fi­cul­ty find­ing her seat at the 2025 Gram­mys, none oth­er than Tay­lor Swift stepped in to help. Swift made sure to “hold space” for Eri­vo, lit­er­al­ly call­ing her to join her at the table, and they shared a seat togeth­er. This moment didn’t just make head­lines for its sweet gesture—it quick­ly turned into a viral meme.

Fans couldn’t stop talk­ing about Swift’s kind act, espe­cial­ly after the actress was seen grab­bing Erivo’s fin­ger in a way that seemed to mim­ic the infa­mous “hold­ing space” meme from a pre­vi­ous viral moment between Eri­vo and Ari­ana Grande. The whole inter­ac­tion was a gen­uine act of kind­ness, but it left fans chuck­ling and ques­tion­ing if it was a bit too staged.

4. Trevor Noah’s Mispronunciation of “Hawk Tuah”

Trevor Noah is known for his wit­ty and sharp com­men­tary, but dur­ing the 2025 Gram­mys, his pro­nun­ci­a­tion of “Hawk Tuah” left many view­ers scratch­ing their heads. As the host intro­duced the artist, Noah stum­bled over the name, pro­nounc­ing it as “hook twa.”

The blun­der didn’t go unno­ticed, and social media was quick to respond, with one view­er jok­ing, “Thank you Trevor Noah for mak­ing me explain ‘Hawk Tuah’ coin to my mom.” While Noah’s South African accent may have caused con­fu­sion, the mis­pro­nun­ci­a­tion quick­ly became a run­ning joke through­out the cer­e­mo­ny.

5. Bianca Censori Bares It All on the Grammys Red Carpet

Bian­ca Cen­sori, wife of rap­per Ye (for­mer­ly Kanye West), made waves at the 2025 Gram­mys with a high­ly reveal­ing out­fit. Cen­sori stepped onto the red car­pet wear­ing a com­plete­ly see-through dress, spark­ing an imme­di­ate back­lash. The ensem­ble, which left very lit­tle to the imag­i­na­tion, caused quite a stir, with many view­ers ques­tion­ing the appro­pri­ate­ness of such an out­fit for a pres­ti­gious event like the Gram­mys.

Reports soon fol­lowed claim­ing that the cou­ple was escort­ed out by secu­ri­ty after the inci­dent, though some sources lat­er clar­i­fied that they left vol­un­tar­i­ly. Regard­less, this fash­ion choice was undoubt­ed­ly one of the most awk­ward and talked-about moments of the night.

Bian­ca Cen­sori and Kanye West turn heads at the 2025 Gram­mys – fash­ion tri­umph or over the top? Watch the video and decide for your­self!

6. Jaden Smith Wears a Castle on His Head

Jaden Smith’s fash­ion choic­es have often been uncon­ven­tion­al, but at the 2025 Gram­mys, he took things to a whole new lev­el by wear­ing a mas­sive cas­tle head­piece. The 26-year-old star made an entrance in a black Louis Vuit­ton suit, but it was the sculp­tur­al “Vam­pire Cas­tle” head­piece by ABODI that tru­ly made him the cen­ter of atten­tion.

The ridicu­lous nature of the head­piece sparked an out­pour­ing of online crit­i­cism, with one social media user com­ment­ing, “Looks like a Hal­loween out­fit for a 5‑year-old.” The out­landish acces­so­ry was cer­tain­ly a con­ver­sa­tion starter, but not every­one was a fan of Smith’s bold choice.

7. Keltie Knight’s Red Carpet Fall

E! News cor­re­spon­dent Keltie Knight suf­fered a high­ly embar­rass­ing moment at the 2025 Gram­mys when she tripped and fell on the red car­pet. Dressed in a stun­ning Ate­lier Zuhra strap­less chain­mail gown, Knight stum­bled in her tow­er­ing Aquaz­zu­ra plat­form heels, draw­ing gasps from the audi­ence.

While the fall was cer­tain­ly cringe-wor­thy, Knight took it in stride, shar­ing the moment on Insta­gram with the cap­tion, “WHY DOES SOMETHING HAPPEN ON EVERY RED CARPET. JUST LET ME LIVE.” Despite the mishap, Knight’s resilience and sense of humor won her fans.

8. Babyface Snubbed for Chappell Roan

One of the more awk­ward moments at the 2025 Gram­mys hap­pened dur­ing an inter­view when reporters were caught snub­bing 13-time Gram­my win­ner Baby­face in favor of first-time Gram­my win­ner Chap­pell Roan. As Baby­face polite­ly attempt­ed to engage in con­ver­sa­tion with the reporters, they sud­den­ly shift­ed their atten­tion to Roan, caus­ing the leg­endary singer to walk away in frus­tra­tion.

The moment sparked online debates about pro­fes­sion­al­ism, with some fans crit­i­ciz­ing the reporters for their lack of respect toward Baby­face. Even­tu­al­ly, an apol­o­gy was issued, but the awk­ward­ness was pal­pa­ble.

9. Clairo’s Reaction to “Bisexual Men of Brooklyn” Question

Dur­ing a red car­pet inter­view, Clairo found her­self in an uncom­fort­able posi­tion when an inter­view­er asked if she had any­thing to say to the “bisex­u­al men of Brook­lyn” who believed she made music specif­i­cal­ly for them. The singer was vis­i­bly tak­en aback, reply­ing with a long, awk­ward “Umm­m­m­mm…” before the inter­view­er awk­ward­ly moved on.

The awk­ward­ness of the moment was not lost on social media, with fans call­ing out the interviewer’s inap­pro­pri­ate ques­tion. Many agreed that Clairo han­dled the sit­u­a­tion with grace, but the exchange cer­tain­ly made view­ers cringe.

10. The Weeknd’s Surprise Performance After Grammys Boycott

The Weeknd’s return to the Gram­mys was a major sur­prise, con­sid­er­ing his pub­lic boy­cott of the event fol­low­ing the snub­bing of his “After Hours” album in 2021. How­ev­er, after four years of absence, The Week­nd shocked fans by per­form­ing at the 2025 Gram­mys, lead­ing to mixed reac­tions from those who remem­bered his strong stance against the awards show.

Despite his sur­prise per­for­mance, many felt con­flict­ed about his return, espe­cial­ly giv­en his pri­or crit­i­cisms. The per­for­mance was pow­er­ful, but the under­ly­ing ten­sion around his appear­ance cre­at­ed a bit of awk­ward­ness through­out the night.

11. Will Smith’s Return to the Grammys

Will Smith made his first appear­ance at the Gram­mys since the infa­mous “slap” inci­dent at the Oscars, lead­ing to a mix of reac­tions. Some fans were hap­py to see him back, while oth­ers ques­tioned why he was allowed to attend, giv­en his ongo­ing ban from the Acad­e­my Awards.

While Smith pre­sent­ed a trib­ute to Quin­cy Jones, his appear­ance caused some dis­com­fort, with many view­ers express­ing their opin­ions on social media. Regard­less of the con­tro­ver­sy, Smith’s return was a major talk­ing point at the 2025 Gram­mys.

12. Trevor Noah’s Offensive Joke During the Opening Monologue

Trevor Noah, known for his sharp wit and humor, made a con­tro­ver­sial state­ment dur­ing his open­ing mono­logue at the 2025 Gram­mys. In a joke about Shaki­ra, he said, “the great­est thing to come out of Colom­bia that isn’t a Class A felony.” The remark was met with back­lash from view­ers, espe­cial­ly those of Colom­bian descent, who found the com­ment offen­sive and insen­si­tive.

Noah’s joke, along with oth­er con­tro­ver­sial remarks about “ille­gal immi­grants,” sparked out­rage online, lead­ing many to call for an apol­o­gy.

13. Charli XCX’s Performance Interrupted by Commercial Break

Char­li XCX’s high­ly antic­i­pat­ed per­for­mance at the 2025 Gram­mys was unfor­tu­nate­ly cut short by a com­mer­cial break, leav­ing fans frus­trat­ed. While the lights were flash­ing and the crowd was danc­ing, view­ers at home missed part of her per­for­mance, caus­ing an out­pour­ing of dis­ap­point­ment on social media.

While the inter­rup­tion was beyond her con­trol, it still left a sour taste for those who were excit­ed to see Char­li XCX’s full per­for­mance.

14. Benson Boone’s Crotch Grab During Performance

Ben­son Boone’s per­for­mance at the 2025 Gram­mys was marked by an awk­ward moment when he appeared to grab his crotch mid-per­for­mance. The unex­pect­ed ges­ture quick­ly went viral, spark­ing a flood of reac­tions from view­ers.

Fans and crit­ics alike ques­tioned the choice, with many find­ing it uncom­fort­able to watch. Some spec­u­lat­ed that Boone was just try­ing to adjust, while oth­ers found the moment over­ly inap­pro­pri­ate for such a pub­lic stage.

15. Kacey Musgraves and Lainey Wilson’s “Shady” Reactions to Beyoncé’s Win

When Bey­on­cé made his­to­ry by win­ning the Gram­my for Best Coun­try Album, the reac­tions from Kacey Mus­graves and Lainey Wil­son didn’t go unno­ticed. Their facial expres­sions dur­ing the announce­ment sparked a wave of crit­i­cism from fans, with many point­ing out their appar­ent lack of enthu­si­asm.

The moment quick­ly went viral, with social media users debat­ing whether their reac­tions were a sign of jeal­ousy or dis­ap­point­ment. The dra­ma added anoth­er lay­er of awk­ward­ness to an already intense night of com­pe­ti­tion.

Catch the 4 most cringe-wor­thy moments from the 2025 Gram­my Awards – awk­ward, unex­pect­ed, and total­ly unfor­get­table!

Conclusion: The 2025 Grammys—A Night of Unforgettable Awkwardness

The 2025 Gram­my Awards will undoubt­ed­ly go down in his­to­ry as one of the most awk­ward cer­e­monies to date. From mis­pro­nun­ci­a­tions and fash­ion dis­as­ters to uncom­fort­able inter­view moments and con­tro­ver­sial jokes, the evening was full of cringe-wor­thy moments that left fans buzzing long after the event end­ed. But, despite the awk­ward­ness, it also gave us plen­ty to talk about, prov­ing that the Gram­mys aren’t just about cel­e­brat­ing music—but also about the unfor­get­table, uncom­fort­able moments that come with it.