Green Day's American Idiot was a tower of unlikely events. The pop-punk trio's seventh studio effort took shape after a batch of their recordings had been stolen from a studio, causing them to regroup and devise a concept album about disaffected youth in early 20th century America - one with two songs approaching the 10-minute mark. It's not an album you'd expect to be one of their biggest hits - nor one to contain their highest-charting single. But that's the case for "Boulevard of Broken Dreams."
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Frontman Billie Joe Armstrong said he got the idea for the song by doing exactly what's sung in the verses: walking alone. In search of more song ideas during a stay in New York City, Armstrong came up with this heart-on-sleeve anthem, drawing further inspiration from Gottfried Helnwein's painting of the same name. (In the portrait, a series of long-gone matinee idols, including James Dean, Elvis Presley and Marilyn Monroe, occupy a city diner similar to the one in Edward Hopper's Nighthawks painting.)
As the second single from American Idiot, "Boulevard of Broken Dreams" - accompanied by a striking, soundstage-set video directed by Samuel Bayer - surpassed everyone's expectations, even for the already-successful album. It climbed the Billboard Hot 100 all the way to No. 2, only the second time they'd ended up anywhere on the chart. It would go on to win a Grammy Award for Record of the Year and a Video of the Year Moonman at the MTV Video Music Awards - the only song to win both.