"Funny how falling feels like flying…for a little while," he sings.
The sharp, evocative line mirrors Bridges' soaring performance as Bad Blake, a late-stage alcoholic who seeks redemption and a second chance through an improbable love affair with a small-town reporter, played by Maggie Gyllenhaal.
Blake is a music industry veteran, both burning out and fading away. He can't write songs like he used to and he's haunted by the outsized success of his young, former protégé, Tommy Sweet, played by Colin Farrell. Sweet, with his ponytail and earrings, represents a new era of commercially-successful country/pop stars.
Bridges' character, by contrast, is pale, pudgy, and constantly out of breath, wheezing as he lights each new cigarette with the dying ember of his last one, over and over, until you can feel your chest tighten.
But when he takes the stage, anywhere, even a bowling alley, the audience's reverence is palpable.
"That's his home turf, that stage,'' Bridges said in a recent interview for ABC News' "Popcorn With Peter Travers." "That's his throne, he can be totally at peace up there."
But the peace seems always short-lived.
"He's kind of hit the wall as far as the song thing. He feels he can't come up with a good song, and he wishes he was like Leonard Cohen or Bob Dylan, one of these great guys, and that's probably the reason he drinks,'' he said. "He's pretty damn good. But [Dylan and Cohen are] in a class… you know, all by themselves."
As Blake works his way back from the bottom, a song slowly emerges from the mess of his life, which shapes and defines the movie.
Bridges originally turned down the script "because there was no music, and it was all about music."
But a year after he originally passed on it, Bridges' old friend, music producer T-Bone Burnett, convinced him to give the script another look.
During filming, Bridges said, Farrell met Ryan Bingham, a struggling, young country artist who was living out of his car at the time. He was cast in a supporting role as a young guitarist backing Blake at the bowling alley gig.
Burnett and writer/director Scott Cooper were still casting about for the right music to fit the story, and one night Cooper got a call from Bingham.
"He's a very humble guy,'' Bridges said of Bingham, "and he said, 'I think I might have a song for you, that you might consider.' And Cooper said, 'come on over to Bone's house and play it. And he sat there on T-Bone's coffee table and played us this remarkable song that he wrote… inspired by the movie, and it fit perfectly.
"And I remember seeing T-Bone's face when he heard that thing and just how wonderful it is… like, 'we got our song! Oh God!'''
The song, "The Weary Kind," became the movie's theme song. It won the Academy Award for best original song (watch the acceptance speech here). Bridges won the 2010 Oscar for Best Actor, after winning a Golden Globe for the performance. Gyllenhaal was nominated for Best Supporting Actress.