Easiest 5 I will ever give, but really difficult to choose the best album. I went for Rain Dogs in the end as there is so much variety on there and for me it’s the perfect link between his singer-songwriter past to his experimental future.
My favourite of his early records is Heart of Saturday night. Really great jazzy songwriter stuff with some heartbreaking ballads.
You could make a good case for Small Change being his best record. A bit more strangeness entering the mix amongst the beat poetry and schmaltz.
Franks Wild Years pushes Rain Dogs close for me. Cold cold ground and train song at the end of that record are devastating.
If I’m in the mood for something darker then Bone Machine is where I go. I don’t wanna grow up and that feel towards the end of the record are quite fun in Waits type way.
In terms of his later records, I love Alice and Bad as Me. Bad as me is kind of similar to Rain dogs in that it covers a lot of ground in Waits’ discography.
Love this man. I’ll post some links to songs later.