I tried him out back in the day but I listened to his newer stuff and didn't appreciate it. I'm starting with his first few albums and working my way up to his more experimental stuff.
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Re: Any Tom Waits fans?
I feel kind of similar to the Prof. There times for Waits and there times not for Waits. I suppose that goes for a lot of music, but especially for him because his music can be sometimes difficult to listen to.
I find his early works much easier listening, it's mellow jazzy music. I've been spining Closing Time (1973) and The Heart of Saturday Night (1974) for the past two nights. I think from Swordfishtrombones-onward he began to take his music into a more avant-garde direction. His first few albums were on the Asylum label, I think when he jumped over to the Island label he began to produce his own music, hence the freedom to experiment.
He sure has a heck of a voice on his early albums, before he drowned it in whiskey and cigarettes. I found this video of him on Letterman...and whether you like his voice or not (or are in the Tom Waits mood ), you have to give him some appreciation for his stage performance:
Any Tom Waits fans?
), you have to give him some appreciation for his stage performance: 
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