Songfacts®:

• Naming a song after an aesthetic defect is strange, but the real meaning of "Crooked Teeth" is even stranger.
  
  In a VH1 Storytellers appearance, Death Cab guitarist Ben Gibbard explained that the song is about two derelicts "keeping themselves captive" in a nowhere town in southern Florida. They wander around, get drunk, and dodge kids strung out on homemade speed while remaining trapped in a poverty cycle of their own making.
  
  Gibbard was inspired to write the song because he wanted to do with music what Raymond Carver did with literature. Carver was one of America's preeminent short story writers and focused much of his work on the lives of people in small towns, particularly people who were on the lower ends of the socioeconomic spectrum and living in some degree of desperation.
• The "crooked teeth" in the song refers to the Florida skyline, which is compared to "the mouth of a man who was devouring us both." Of course, neither the skyline nor the state are doing anything – the characters in the song are doing it to themselves.
• Plans, Death Cab's fifth studio album, hit stores in 2005, but the band didn't release "Crooked Teeth" as a single until February 2006. It was the second single off the album, following "Soul Meets Body."
  
  They released multiple versions of the song in the US, UK, and Europe, some with their song "Talking Like Turnstiles" as the B-side, some with a cover of Julian Cope's "World Shut Your Mouth," and some with both. The single spent 19 weeks on the Alternative Airplay chart (called Hot Modern Rock Tracks since 2020) and peaked at #10 on April 29, 2006.