Songfacts®:

• In this song, Tom Waits narrates a Christmas card written by a hooker and sent to a former boyfriend of hers named Charlie. For most of the song, she tells Charlie that she's pregnant and has cleaned up her life. She's got an "old man" who plays trombone and stays in shape working out at the track. It's a loving, healthy relationship, the narrator tells us, and they're going to get married.
  
  As the story goes, however, the narrator begins to reveal that she misses Charlie. She thinks about him every time she passes a gas station because of all the grease he wore in his hair. She also mentions that she wishes she still had all the money they'd spent on dope (the "we" here tells us a lot about Charlie).
  
  By the song's final verse, she drops her charade completely and reveals the real situation: She has no money and no man, and she's back in jail and needs to borrow money for a lawyer.
  
  The song finishes with her subtle offer for reunion with the line, "I'll be eligible for parole come Valentine's Day."
• In the song's third verse, she mentions that she still has the Little Anthony and the Imperials record that Charlie gave her. Throughout the late '70s, Waits played "Christmas Card from a Hooker in Minneapolis" as a medley with "Goin' out of My Head," which was the signature song of Little Anthony and the Imperials.
• At at some notable holiday performances in the '70s, Waits would open with "Silent Night" and transition into "Christmas Chard from a Hooker in Minneapolis."
• In New York City on November 21, 1985, Waits preempted a performance of the song with a story. "I was in Minneapolis – it was 200 degrees below zero – I know, you think I'm bulls--tting, no, I swear to God, I was wearing just a bra and a slip and a kind of dead squirrel around my neck – he was colder than I was. The police cars would go by and they'd wave... merry Christmas, merry Christmas, merry Christmas... anyway, I got caught in the middle of a pimp war between two kids in chinchilla coats, they couldn't have been more than 13 years old. They're throwing knives and forks and spoons out into the street – it was deep – so I grabbed a ladle, and Dinah Washington was singing 'Our Day Will Come' and I knew that was it."
  
  The story is very similar to the one he's told regarding "Ninth And Hennepin," which is also set in Minneapolis.
• Neko Case recorded a notable cover of the song on the New Coat of Paint Tom Waits tribute album, released in 2000.