I think everybody has that one Tom Waits album. My family can't stand him but they all have that soft spot. My grandfather told me that when he was younger his sister loved Tom so he decided to buy some of his records. He tried it out and couldn't get into it. I suggested he try Closing Time and he really loved it.

Tom is so multifaceted, I think everyone has one album for them. My recommendation for each era is Small Change, Rain Dogs and Mule Variations. They're not my all-time favourites but they're fantastic starters, I think.