The title of this autobiographical song is named for the street Tom Waits grew up on in Whittier, California. He started nabbing cigarette butts out of the gutter when he was 7 years old.
Many of the characters from this song are based on real people. Joey Navinski, the one who bragged about French-kissing Hilda the strip poker player, was a neighborhood kid who played the trombone, and Dicky Faulkner, who's "got a switchblade and some gooseneck risers," was known for always having a runny nose. Waits also wasn't exaggerating when he sang, "Mrs. Storm will stab you with a steak knife if you step on her lawn." The real Mrs. Storm lived with her sister and would sit by her kitchen window armed with a 12-gauge shotgun.
Waits' childhood best friend was a boy named Kipper who had polio. He sings of wanting to free him from his wheelchair and leg braces. He told Smash Hits magazine in 1981:
"I didn't understand what polio was. I just knew it took him longer to get to the bus stop than me... Sometimes I think kids know more than anybody. I rode a train once to Santa Barbara with this kid and it almost seemed like he lived a life somewhere before he was born and he brought what he knew with him into this world and so... it's what you don't know that's usually more interesting. Things you wonder about, things you have yet to make up your mind about. There's more to deal with than just your fundamental street wisdom. Dreams. Nightmares."
The lyrics to "Heartbreak Hotel" were written by a steel guitar player who was once a dishwasher repairman. He was inspired by a newspaper story about a man who killed himself and left behind a note saying only, "I walk a lonely street."