Boulevard of Broken Dreams

Armstrong wrote Boulevard of Broken Dreams during the few weeks he spent alone in New York in 2003, as a song about feeling alone in the city and trying to take power from that. He played an almost finished demo to Cavallo, who felt it was unlike anything the band had made and believed it would be a success. It was recorded at Ocean Way Recording. The title comes from a Gottfried Helnwein painting of James Dean, Humphrey Bogart, Marilyn Monroe and Elvis Presley in a diner. Within the story of American Idiot it follows Holiday, and MTV described Holiday as a party and this song as the hangover. The chord progression is the same as Oasis's Wonderwall, and Noel Gallagher criticised Green Day for it.

It peaked at number two on the Billboard Hot 100, the highest position of any Green Day song there, and was the first song to top the Mainstream Rock, Modern Rock, Adult Top 40 and Mainstream Top 40 charts together. It reached number five in the UK. The song won the Grammy for Record of the Year in 2006. Samuel Bayer directed the video, which won six MTV Video Music Awards in 2005 including Video of the Year. After Hurricane Katrina the band gave the year's iTunes proceeds from the song to the American Red Cross.

Live

The band played it at the opening ceremony of Super Bowl LX on 8 February 2026, after Holiday.