and Timothée Chalamet were supported by loved ones on Sunday after a chastening night at the 96th annual ended in bitter disappointment.
Chalamet had been hot favourite to claim Best Actor for his starring role in Marty Supreme after an auspicious start to awards season saw him triumph in the same category at the Critics Choice and .
But the actor instead found himself the butt of numerous jokes courtesy of host Conan O'Brien for a series of ill-timed and highly dismissive comments about opera and ballet during a recent pre-Oscars interview.
He would later be forced to sit and watch as Michael B. Jordan won Best Actor for Sinners, with Chalamet, 30, looking visibly disappointed as he applauded the American star.
But the actor had support in the form of his devoted mother Pauline as he left Hollywood's Dolby Theatre empty handed.
Likewise Jenner, a shell-shocked spectator as Chalamet's recent dismissal of opera and ballet came back to haunt him, was joined by her own mother, , and older half-sister as they made their way to the Vanity Fair after-party.
Kylie Jenner and Timothée Chalamet were supported by loved ones on Sunday after a chastening night at the 96th annual Academy Awards ended in bitter disappointment
While Chalamet dominated the early season with Best Actor wins at the Golden Globes and Critics' Choice Awards for ping-pong drama Marty Supreme, the momentum shifted after Jordan won at the Actor Awards, formerly known as the SAG Awards, earlier this month.
Adding to the tension, the Oscars arrived on the heels of Chalamet's controversial comments about 'noone' caring about opera and ballet, which sparked a wave of backlash from the arts community, including from legendary director Steven Spielberg.
Chalamet made the unfiltered remark while talking to Interstellar co-star Matthew McConaughey about his hopes that movie theaters are able to survive.
He then added that 'I don't want to be working in ballet or opera or, you know, things where it's like: "Hey, keep this thing alive," even though no one cares about this anymore,' in an interview for Variety's Actors on Actors.
Conan O'Brien, who returned as host of the Academy Awards for the second consecutive year, kicked off his opening monologue with a jab at Chalamet's controversy.
'Security is extremely tight tonight. I'm just going to mention that,' tuxedo-clad O'Brien said to the crowd inside Los Angeles' iconic Dolby Theatre.
He then quipped, 'I'm told there's a concern about attacks from both the opera and ballet communities.'
The camera then quickly cut to Chalamet, who could be seen nervously smiling beside his busty girlfriend.
'They're just mad you left out jazz,' O'Brien jokingly added.
The actor had support in the form of his devoted mother Pauline as he left Hollywood's Dolby Theatre empty handed
Jenner's half-sister Kim Kardashian joined her at the Vanity Fair party on Sunday evening
Kardashian flashed a peace sign outside the Los Angeles County Museum of Art (LACMA)
Chalamet was seen following his girlfriend out of the venue, where Kris Jenner was also on hand to support the couple
The Kardashian matriarch looked appropriately glamorous in a billowing black evening gown
O'Brien tried but failed to make amends with Chalamet later in the night as he told the crowd he and the Marty Supreme star were 'vibing.'
'We're vibing, right?' he asked Chalamet, whose reply wasn't picked up by the event's microphones. 'He doesn't think so.'
