Awkward Justin Timberlake Moments He Wishes We'd Forget About

Justin Timberlake has won a slew of awards, but he also has a laundry list of awkward moments that might come to mind sooner than remembering what he won his seventh Grammy for. (It was for "Suit and Tie," and he shared it with his track partner, Jay-Z). And while the Prince of Pop may be known to have a funny bone — hence his induction into "Saturday Night Live"'s hallowed "Five Timers Club" — he also has plenty of moments that have made us laugh at him instead of with him.

The former *NSYNC band member and "Trolls World Tour" star has plenty of controversial moments to pull from. After all, he started his career as an entertainer when he joined "The Mickey Mouse Club" at just 12 years old, and at 43 years old at the time of this writing, he's still in the spotlight. But while he continues to entertain the world over, he has also found new, and more adult ways, to make it awkward for all of us adoring fans. Sure, there is something comforting about watching Timberlake grow up alongside us, with some of his top awkward instances reflecting the cultural moments we've all lived through. But we "Can't Stop The Feeling" that he might wish we could forget all of the following incidents.

This is one awkward moment that might end up on Justin Timberlake's permanent record. In June 2024, the "SexyBack" pop star was driving to a friend's house through Sag Harbor, New York when he was pulled over by a police officer who asked if he had been drinking that night. After declining a breathalyzer but failing a number of field sobriety tests, he was told that he was being arrested and brought to the station.

That's when Timberlake uttered seven words that made the entire Internet cackle. "This is going to ruin the tour," he reportedly muttered under his breath to the arresting police officer, as Page Six reported. The officer then cluelessly replied, "What tour?" One can almost imagine the exasperation in Timberlake's voice that the officer didn't recognize him when he allegedly responded, "The world tour." His tour in question was Timberlake's "Forget Tomorrow World Tour", which almost became an even more appropriate title when it was thrown into question pending his sentencing. But Timberlake was later released and closed out the case with a plea deal, requiring him to only pay $500 and do 25 hours of community service.

With Justin Timberlake's tour almost done in by his aforementioned DWI charge, one would think that fans would savor the time they get to spend with him at shows. That was not the case in Brooklyn, New York, while Timberlake was singing his song "Flame". While performing, he noticed a young woman with her eyes glued to her phone at the edge of the stage. In a video posted to TikTok, Timberlake notices the girl and bends down, singing right above her — only for her to completely ignore him.

Timberlake quickly leaves her to her texting, and as soon as he departs, the girl looks up and realizes her mistake, quickly grabbing at his leg. While the moment may be more awkward for the distracted fan than for Timberlake, internet commenters were quick to wonder what kind of person purchases front row tickets to a Justin Timberlake concert and spends any amount of time looking down at their phone. It was a lesson in karma, and as the Grammy-award winning artist sang himself, "What goes around ... Comes around."

In Britney Spears' memoir, "The Woman In Me," she recalled a time when she and then-boyfriend Justin Timberlake met the R&B artist Ginuwine. "One day J and I were in New York, going to parts of town I'd never been to before," she wrote. "Walking our way was a guy with a huge, blinged-out medallion." The man with the medallion apparently was Ginuwine, which reportedly prompted Timberlake to greet him by saying, "Oh yeahhhh. Fo' shizz. Fo' shizz. Ginuwineeee, what's up homie?" While the cringe-worthy statement might be hard enough to read in print, what really made the moment go viral was the memoir's audiobook narrator having to pronounce the awkward moment for listeners to hear with their own ears.

Apparently Ginuwine had no recollection of Timberlake's eye-rolling opener. "Nah, I don't remember that," he told Billboard. "I would have probably looked at him very weird if he did that like she said. I just don't remember that, but I remember him [Timberlake] being a cool dude and me kicking it down there in Florida with [*NSYNC's] producer at one time." Still, Timberlake has a history of adopting a "blaccent" as a white entertainer who dabbles in traditionally Black music genres like soul, hip hop, and R&B. And one internet sleuth on X, formerly known as Twitter, was quick to find additional evidence of his awkward attempts, this time posting a video of him doing a laughably outdated beatboxing routine in a sequined bandana.

Honestly, Justin Timberlake should get a pass on this one. Sitting on a couch next to his mother, ABC's Barbara Walters sat across from them and drolly inquired about his fellow popstar and recent ex-girlfriend Britney Spears. The next question was a point-blank ask of whether or not Timberlake and Spears upheld their promise to abstain from premarital sex. Timberlake's wild chuckle and sputtered answer of "sure" is about as honest and awkward as it can get.

The 2002 moment ranks supreme in the echelon of Justin and Britney moments only because it spoke exactly to the delicate dance that the two celebrities had to play with the media. The sky-high levels of awkwardness stems from the fact that two of the hottest pop stars in the world also had to pretend to be the most pure and innocent in an industry that sold sexiness as its most profitable commodity. But the stilted answer would serve as a footnote in the eventual rollout of Spears' memoir, where she would clear the puritanical air. She no longer needed to laugh and lie like Justin did as she confessed that her first lover was not Timberlake and was in fact her brother's best friend when she was a freshman in high school.

Justin Timberlake gave us a clue into his accent enthusiasm while accepting his American Music Award in 2013 for favorite soul/R&B male artist. After being handed the award by Ciara and Paulina Gretzky, Timberlake's first words at the microphone were, "Shut up!" But it was just a joke — his family was sitting in the nosebleed section and were loudly cheering him on. He managed to stay the course and talk about how he was humbled to have been nominated in the categories of pop, rock, and then soul and R&B — and then got a little sidetracked.

Timberlake looked up into the audience and asked, "Can we talk about how cute Rihanna's mom is?" But what could have been left as a quick and complimentary gesture then became something far more awkward when Timberlake doubled down. "How cute Rihanna's mom is?", he again asked the audience, but this time attempted to say it in Rihanna's mother's native Bajan accent. Timberlake may have picked it up when Rihanna's mother, Monica Braithwaite Fenty, had earlier presented her daughter with the Icon Award, but it's unclear why he felt the need to reenact it. Wild eyed and looking a bit unsure if he should be doing what he's doing, Timberlake nevertheless confidently continued, ending his version of a Bajan accent with a heavily inflected, "She's so proud of the icon." Maybe with all of these accents coming back to bite Timberlake, it might be best to stick to some kind of Tennessee drawl. After all, it's where he was born.