Songfacts®:

• "Oscar Winning Tears" is the kind of song that sweeps you back to the smoky glow of a jazz club full of horns, strings, and a classic 6/8 rhythm. On the surface, it's a big-band ballad, but dig a little deeper and you'll find a bold story of betrayal, emotional manipulation and self-discovery. In the song, Raye takes aim at the sort of relationship where one partner's remorse looks as polished as an Oscar performance, and the other's left feeling like a stunned audience to a drama that's just too much - and far too fake.
• This theatrical metaphor isn't just for effect. Raye wrote the song after a chilling experience when her drink was spiked by a man she knew and trusted. "When it happened, he was right there, crying in my face like he was the one hurt," she told Apple Music. "I was like, 'Wow, I have a song for this.' It was liberating."
• "Oscar Winning Tears" is the first full track on Raye's debut album, My 21st Century Blues, a project she recorded with producer Mike Sabath (Shawn Mendes, Jade). Sabath helped shape the album into a genre-bending exploration of Raye's own experiences with addiction ("Escapism"), sexual assault ("Ice Cream Man"), misogyny ("Hard Out Here") and insecurity ("Body Dysmorphia").
  
  "When we finished it, I knew this had to be the start," said Raye. "I think the initial concept and then the story ended up just merging so perfectly into just a beautiful piece of medicine for me."
• My 21st Century Blues distills the feeling of a live set at a middle-American jazz club. It opens with a prelude titled "Introduction," where a "MC" welcomes Raye to the stage. The spotlight then lands on "Oscar Winning Tears."
  
  "Even though it's a really classic-sounding six-eight, and we've got gorgeous strings in there... it's actually a story for anyone who's been severely gaslit," she described to MTV News.
• Raye wasn't invited to the Oscars but did get to sing "Oscar Winning Tears" at the Grammy Awards in 2025, where she was nominated for Best New Artist (which went to Chappell Roan) and Songwriter Of The Year (which went to Amy Allen). Host Trevor Noah called Raye "Your favorite singer's favorite singer."