Boulevard of Broken Dreams (feat. John Gallagher Jr., Rebecca Naomi Jones, Stark Sands, The American Idiot Broadway Company)

This song is about estrangement and the recognition that the American Dream can let you down. The singer's hopes have been crushed, and he finds himself very much alone. "It's just about loneliness," Armstrong told People in a 2024 interview. "Anytime that I would be writing songs for a record, you feel like a sense of isolation. At that time, I went to New York by myself. I was staying in an apartment, and I was there for quite some time - over a couple months - and I was just trying to focus on writing [American Idiot] with no distractions. There can be all of this chaos going on around you, but ultimately you can find yourself pretty alone in the world."

This follows the main character from Green Day's song "Jesus Of Suburbia." He leaves town, has one crazy first night, and now it's kind of like the hangover. He's just walking, thinking about whether it was the right decision leaving where he used to live.

"Boulevard Of Broken Dreams" is a famous painting by Gottfried Helnwein depicting Marilyn Monroe, Humphrey Bogart, James Dean and Elvis Presley hanging out in a bar. Helnwein's painting is a parody of a painting called "Nighthawks" by Edward Hopper. In a VH1 Storytellers session, Green Day frontman Billie Joe Armstrong said he saw the title on another Helnwein painting of James Dean from 1948. "There's an old James Dean photo where he's walking in New York and underneath it says 'Boulevard of Broken Dreams.' It's a great photo of him, so that's where I sort of nicked the title from," he said.