Awkward Timothée Chalamet Moments Seen By Millions

Timothée Chalamet is one of the biggest movie stars of the moment. From showing off his musical chops in "Wonka" to reprising his leading role in "Dune Part 2," Chalamet's career is on fire. The actor has plenty of fans thanks to both his charming and humble nature offscreen and his show-stopping acting onscreen. But, despite the recognition he gets and the fanbase he's garnered, this actor has had more than his fair share of awkward moments during his time in the spotlight.

Being a celebrity can't be easy. With paparazzi following you around to get the perfect shot when you least expect it to fans dredging up things you did and said in your youth and posting them all over the internet, being famous gives you more than enough opportunity to be embarrassed in front of millions of people. Chalamet knows this firsthand. And, while we don't blame the star for the rather cringeworthy situations we've seen him in, that doesn't mean that his fanbase hasn't been given quite a few reasons to get the ick. From several different musical numbers we wish we could forget to some PDA-ridden moments that will live on forever in Hollywood history, Chalamet's awkward moments in front of the world are unfortunately plentiful. And these are the worst of the worst.

Plenty of people were surprised to hear that Timothée Chalamet had been cast as the titular character in "Wonka," the 2023 movie musical based on the character from Roald Dahl's famous novel, "Charlie and the Chocolate Factory." Still, whether you thought Chalamet was a good fit for the iconic role or not, most of us can agree that casting Hugh Grant as an Oompa Loompa was a far more unexpected choice. Surprising or not, Grant played the Oompa Loompa to Chalamet's Wonka, and the film's press junket proved that these two were happy to act alongside each other, as their mutual respect was evident. In many interviews, the two actors spoke highly of each other and their work. At "Wonka's" Tokyo premiere, however, Chalamet didn't just speak highly of his costar, he sang highly of him, too. And, it was enough to give fans a heaping dose of secondhand embarrassment.

When speaking at the premiere, Grant told the audience that Chalamet "is very good in" Wonka. Chalamet, in turn, said that Grant is also very good in the film. The audience cheered in response, which inexplicably prompted Chalamet to do his own rendition of the classic Oompa Loompa song from the original 1971 film, "Willy Wonka & the Chocolate Factory." The audience and Grant laughed along, but that doesn't mean that we weren't a little bit embarrassed on Chalamet's behalf. 

Whether you're a Timothée Chalamet fan or you simply come across news about the actor's life on the internet now and then, there's one not-so-flattering moment in the star's life that you've probably seen. In 2019, photos surfaced of Chalamet with then-girlfriend, Lily-Rose Depp, on a yacht together in Italy. The photos showed this pair, who began dating in 2018, getting cozy — very, very cozy. The couple was caught by paparazzi mid-makeout, and the nature of these photos probably would have embarrassed just about anyone in Chalamet and Depp's position. 

And, as it turns out, Chalamet was, in fact, embarrassed. He opened up to GQ about the fallout from the photos. "I went to bed that night thinking that was one of the best days of my life," the star explained. "I was on this boat all day with someone I really loved, and closing my eyes, I was like, indisputably, 'That was great.' And then waking up to all these pictures, and feeling embarrassed, and looking like a real nob? All pale?" It's safe to say that Chalamet would have preferred to keep this moment private. And, consequently, he was particularly confused that folks thought these photos were a publicity stunt organized by him and Depp. He said, "People are like: This is a P.R. stunt. A P.R. stunt?! Do you think I'd want to look like that in front of all of you?!" We can't help but feel for the guy. 

The paparazzi put Timothée Chalamet in an embarrassing situation when they published those photos of him locking lips. However, some of Chalamet's most awkward moments were all his own doing. If you've never heard of Lil Timmy Tim, then prepare to look at Chalamet a little differently. Chalamet's theater kid past landed him his Wonka role, but within that past lies the star's alter ego, a dancing rapper named Lil Timmy Tim.

Lil Timmy Tim was Chalamet's rapper name back in 2012. Chalamet was in high school at the time, and we'll let those among us who don't have a horribly embarrassing high school story in their past cast the first stone. Nevertheless, most of us have been lucky enough not to have our most cringeworthy teenage moments circulating the internet for years. Yet, Lil Timmy Tim has managed to live on for over a decade thanks not only to Chalamet's superstardom, but also thanks to just how impressively embarrassing this performance really is. In it, Chalamet's confidence has already reached record heights, as he sings the lyrics, "It's Lil Timmy Tim, I am a boss. You really like my shirt? Should I take it off?" This was not the only time Chalamet rapped in high school. He also did so for a statistics project, which of course, also made it to YouTube and gained 12 million views. On "The Graham Norton Show," Chalamet revealed that he earned a D on that project.

It never comes as a surprise when a celeb chooses to post a thirst trap or two. Of course, Timothée Chalamet is no exception to this. Yet, when the star took to Instagram in August 2023 to share two shirtless photos of himself, fans were a little surprised at the photos he chose. 

Sure — we can't call Chalamet's thirst traps taken in a cave embarrassing like some of his other awkward moments in the spotlight, but that doesn't mean that they didn't make us cringe and wonder why he chose to post them, at all. The post, which was captioned "summer24!" included two photos. The first image shows a closeup of Chalamet with wet hair and a subtle smirk. This photo wasn't particularly strange, but it was followed up with a more zoomed-out image, showing Chalamet submerged in water inside a cave. The photo didn't look posed, rather it almost looked like he was struggling to stand up amidst the rocks. Fans were left with many unknowns about the photo. Why he was in a cave, whether he was actually struggling to get out of the water, and why he chose to post these images all remain a mystery. 

While Timothée Chalamet's PDA with Lily-Rose Depp continued haunting him for years to come, his kiss with Kylie Jenner at the 2024 Golden Globes may have caused an even bigger stir. Jenner and Chalamet's relationship has had people talking ever since news of the romance went public in April 2023. While these two are both big stars in their own right, they come from very different corners of Hollywood. And, for a lot of the public, the idea of them together was a head-scratcher. While they'd shared PDA before, Golden Globes night was the first time that these two took things quite so public, and how they behaved while all eyes were on them proved that they only have eyes for each other.

Chalamet's PDA with Jenner was notably less embarrassing than his OG viral makeout; the couple was clearly aware of the cameras, gazed lovingly into each other's eyes, and shared a few pecks rather than getting hot and heavy. Still, this may have made bigger waves than Chalamet's previous PDA. Footage of the pair acting lovey-dovey swept the internet, and it was clear that Jenner wanted to support her man, Chalamet wanted to show off his girlfriend, and neither party wanted Chalamet to end up sporting any of Jenner's lipstick. Some may have thought that it was a cute moment, while others were skeeved out, but we can all agree that watching it feels a little bit like we're interrupting something. 

Every year, plenty of folks attend the Golden Globe Awards without becoming the subject of anything particularly newsworthy. At the 2024 Golden Globes, though, Timothée Chalamet went viral for more than just getting cozy with girlfriend, Kylie Jenner. One interaction between Selena Gomez and Taylor Swift that was caught on camera also went viral, and the whirlwind of gossip that followed made for a very awkward moment for Chalamet. During the award show, a video clip was taken that shows Gomez whispering in Swift's ear, eliciting a look of shock from the Eras Tour star. Plenty of amateur lip readers on the internet looked closely at the video and alleged that Gomez told Swift that she asked to take a photo with Chalamet, and Jenner said "no." This took the internet by storm, and plenty of fans wanted to know if there was any truth to the rumor. A few days after Golden Globes night, Chalamet was followed by a TMZ reporter who was looking for answers.

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— v (@ViralThingz) January 9, 2024

The reporter asked, "Hey, did you deny Selena a photo like everyone's reporting?" Chalamet refused to answer despite being followed and repeatedly questioned. Finally, when asked, "Are you and Selena cool?" Chalamet said, "Of course." Many fans on X, formerly known as Twitter, came to Chalamet's defense, condemning the reporter's invasive methods. Whatever you make of Chalamet's response, it was an unquestionably cringe-inducing exchange. But, we think the media can take the blame on this one.