I am an American aquarium drinker I assassin down the avenue I'm hiding out in the big city blinking What was I thinking when I let go of you? Let's forget about the tongue-tied lightning Let's undress just like cross-eyed strangers This is not a joke, so please stop smiling What was I thinking when I said it didn't hurt? I want to glide through those brown eyes dreaming Take it from the inside, baby hold on tight You were so right when you said that I've been drinking What was I thinking when I said good night? I want to hold you in the Bible-black predawn You're quite a quiet domino, bury me now Take off your Band-Aid because I don't believe in touchdowns What was I thinking when I said hello? I'd always thought that if I held you tightly You'd always love me like you did back then Then I fell asleep and the city kept blinking What was I thinking when I let you back in? I am trying to break your heart I am trying to break your heart But still I'd be lying if I said it wasn't easy I am trying to break your heart Disposable Dixie-cup drinking I assassin down the avenue I'm hiding out in the big city blinking What was I thinking when I let go of you? Loves you I'm the man who loves you
I am an American aquarium drinker I assassin down the avenue I'm hiding out in the big city blinking What was I thinking when I let go of you? Let's forget about the tongue-tied lightning Let's undress just like cross-eyed strangers This is not a joke, so please stop smiling What was I thinking when I said it didn't hurt? I want to glide through those brown eyes dreaming Take it from the inside, baby hold on tight You were so right when you said that I've been drinking What was I thinking when I said good night? I want to hold you in the Bible-black predawn You're quite a quiet domino, bury me now Take off your Band-Aid because I don't believe in touchdowns What was I thinking when I said hello? I'd always thought that if I held you tightly You'd always love me like you did back then Then I fell asleep and the city kept blinking What was I thinking when I let you back in? I am trying to break your heart I am trying to break your heart But still I'd be lying if I said it wasn't easy I am trying to break your heart Disposable Dixie-cup drinking I assassin down the avenue I'm hiding out in the big city blinking What was I thinking when I let go of you? Loves you I'm the man who loves you
A faixa de abertura do álbum *Yankee Hotel Foxtrot* narra a história de um homem isolado em grande cidade após um relacionamento tumultuado.
O tema central da canção gira em torno de sentimentos de solidão e culpa que surgem após o fim da relação.
O documentário de Sam Jones, intitulado “I Am Trying to Break Your Heart”, destaca a reação do executivo da Nonesuch Records, David Bither, que ficou empolgado após ouvir apenas os primeiros 30 segundos da música.
O título da música foi tão impactante que serviu de inspiração para o nome do próprio documentário, evidenciando a influência da faixa na percepção crítica do álbum.
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