After he vowed to become 'one of the greats', many predicted that it could finally be time for to secure his first Oscar.
Yet it proved to be third time unlucky for Timothee at Sunday's as he missed out yet again on the top prize, with Michael B Jordan - who became a last minute frontrunner - securing the award.
It's been suggested that Timothee's controversial comments about 'no one caring' about the ballet and opera - and the actor was certainly reminded about them during the lengthy ceremony.
Timothee, 30, was roasted within moments of the show starting, with host Conan O'Brien declaring in his opening monologue: 'Security is extremely tight tonight. I'm just going to mention that.
'I'm told there's a concern about attacks from both the opera and ballet communities!'
The camera then quickly cut to Timothee, who could be seen nervously smiling beside his girlfriend - yet according to body language expert , .
How Timothee Chalamet became the laughing stock of the Oscars in a night of digs about his 'milkman' outfit and ballet comments before he missed out on Best Actor
Michael B Jordan became a last minute frontrunner for Best Actor after Timothee made controversial comments about the ballet and opera - with the Sinners star then winning
Judi told the Daily Mail that Timothee's body language suggested 'a chastened and quite submissive response'.
She explained: 'His cheeks raised and rounded and he displayed his upper teeth only, in a forced-looking grin while Kylie leaned over him protectively, flashing a maternal-looking warning expression from her eyes as well as a tolerant and calm-looking mouth smile.'
Judi added that in response to the joke, Timothee 'opened his mouth wider in an expression of embarrassment and nodded slowly in a gesture of recognition and acceptance.'
The joke also didn't land with Kylie, with Judi noting that the reality star 'looked less comfortable, clenching and unclenching her hands before performing one very odd, loud clap that suggested a desire to get the joke over and move on.'
Despite Timothee's strained reaction to the joke, Judi suggested that he may well have been expecting a roasting, having chosen to wear all-white in a signal of 'innocence'.
Yet his choice of attire wasn't enough to save him from ridicule - and in fact merely added to the teasing.
The three-time Oscar nominee arrived at the ceremony an all-white ensemble of a suit, tie and shoes, which clashed against a massive pair of black shades.
Fans roasted the ensemble on X, formerly Twitter, where one groused: 'he doesn't deserve to come near that Oscar due to this atrocity of a fit.'
Another wondered: 'dear lord Timmy, what on earth inspired this monstrosity,' as one observer joked that the young movie star resembled a 'milkman.'
One dismissed the getup as a 'mess,' while another said in a nod to his romance with Jenner: 'He needs fashion lessons from the Kardashian/Jenner clan.'
Elsewhere in the ceremony, Timothee was also called out by Alexandre Singh on stage as he won Best Live-Action Short Film, for his piece, Two People Exchanging Saliva.
'We believe art can change people’s souls,' Alexandre said. 'Maybe it takes ten years' time, but we can change society through art, through creativity, through theater and ballet - and cinema.'
Timothee also sat through a ballet performance during the ceremony, with ballerina Misty Copeland dancing during the Sinners musical number.
The acclaimed ballerina had previously spoken out against Timothee's comments, saying: 'I mean, he wouldn't be an actor and have the opportunities he has as a movie star if it weren't for opera and ballet, and their relevance in that medium.
'All of these mediums have a space and we shouldn't be comparing them.'
The three-time Oscar nominee was roasted after he arrived at the ceremony in an all-white ensemble of a suit, tie and shoes, which clashed against a massive pair of black shades
Timothee also sat through a ballet performance during the ceremony, with ballerina Misty Copeland dancing during the Sinners musical number
Timothee's Best Actor loss was a miserable end to his seven-year campaign to master the role - during which time he insisted on having a ping pong table around him at all times (pictured in Marty Supreme)
It took seven years to get Marty Supreme off the ground, during which time Timothee went to extreme lengths to master his role as table tennis player Marty (pictured on The Graham Norton Show in December while 'method dressing' on the promo tour
Timothee then suffered another upset when host Conan tried but failed to make amends with the star, as he told the crowd he and the Marty Supreme star were 'vibing.'
'We're vibing, right?' he asked Timothee, whose reply wasn't picked up by the event's microphones. 'He doesn't think so.'
Yet, the ultimate humiliation came near the end of the night, when Timothee missed out on the Best Actor award.
The Marty Supreme looked visibly disappointed when 2025 Best Actor winner Adrien Brody read out Michael's name instead of his, before offering polite applause.
Timothee had had been bookies' favourite to take home the top prize until March 5, when his Variety interview with Matthew McConaughey went viral, in which he said he wouldn't want to work in ballet or opera, because 'no one cares about it'.
With mounting backlash and Oscars voting still open at the time, Michael then became the frontrunner for his work in Sinners, resulting in Timothee suffering an own goal.
It was a miserable end to Timothee's seven-year campaign to master the role - during which time he insisted on having a ping pong table around him at all times.
Speaking with Jimmy Fallon, Timothée explained he was dedicated to mastering the sport, revealing there was a 'six to seven year training process', after he first met with director Josh Safdie about the role in 2018.
'It was a lot of training,' he explained. 'It started during Covid and ping pong is a great thing.
'The gift of my life, the gratitude exercise. I live every morning to go "Wow. For some reason I'm getting the opportunity to work", why not go 10,000% hard.'
Previously speaking to the BBC the A Complete Unknown star said he would 'train as much as possible' in his downtime and with a coach.
This included bringing a ping pong table to the desert while filming Dune and practicing between takes on the set of Wonka.
'By the time the French Dispatch was coming out [in 2021], I was in a beautiful Airbnb on a cliffside for the Cannes Film Festival and I had a table with me... So I have a video of training with friends. It's like a gorgeous sunset.
'I think the responsibility in this movie, like in the Bob Dylan movie, if you were a Dylan fan or a guitar player, [is to make sure] that looks real to you on screen. Similarly here, if you're a ping-pong aficionado, that that looks believable to you.'
Grateful for his success in Hollywood's famously cutthroat industry, he added: 'There's worse things in life than having to learn how to play the guitar and play table tennis at a high level.'
He added: 'This is a movie about sacrifice in pursuit of a dream. And it's something I can relate to deeply.
Timothee also committed to the role by deliberately blinding himself with strong contact lenses that would blur his vision and leave him feeling 'dizzy', forcing him to wear his character's prescription glasses.
Explaining the reasoning, Timothee shared: 'From an actor's perspective, it makes you more impaired, but from an audience perspective, gives me these little beady eyes.
'But that perspective also enhances it. It got me into the world of Marty Reisman, who's living sort of a life of impairment.
'At risk of being pretentious, it's like if you gave an artist three colours instead of nine and said [do a rainbow].'
Even his speech at last year's SAG Awards for A Complete Unknown, was made with his role in Marty Supreme in mind.
During his speech, Timothee expressed his strong ambition and drive, telling his peers: 'I know we're in a subjective business, but the truth is, I'm really in pursuit of greatness.'
One Battle After Another ended the 2026 Oscars by winning Best Picture as director Paul Thomas Anderson accepted the honor beside Teyana Taylor as the honor was presented by Ewan McGregor and Nicole Kidman (seen left to right)
Jessie Buckley continued her winning ways as she earned Best Actress for her role in Hamnet
One Battle After Another was the biggest winner of the evening as Paul Thomas Anderson earned both Best Director and Best Adapted Screenplay
Sean Penn was not in attendance as he earned his third Oscar
Amy Madigan took home the first award at the Oscars 2026 on Sunday night
Ryan Coogler finally earned his first in the Best Original Screenplay category for his epic Sinners
KPop Demon Hunters earned Best Animated Feature Film (Maggie Kang, Chris Appelhans and Michelle L.M. Wong are seen left to right) and Best Original Song for Golden
Amy Madigan took home the first award at the Oscars 2026 on Sunday night.
