friend, you have been missing something in your life.
you have heard tom waits songs, probably played by other people:
"downtown train" (rod stewart), "jersey girl" (bruce springsteen), "ol' 55" (the eagles).
he's one of america's greatest songwriters, but he's got a very selected audience due to the fact that he has a very...distinct voice and songwriting style. started out in the 70's as a folk singer/songwriter, then in the 80's threw that away and became one of the most influential, bizarre guys ever to play an instrument or "sing"...his music's been in soundtracks for "12 Monkeys", "Fight Club" and "Basquiat", and he's been in movies like "mystery men", "down by law", "the fisher king", "ironweed", and even "the outsiders".
he's described as a "beatnik" as well but that kind of cheapens him. he's definitely an acquired taste but once you've acquired it you'll never go back.
if you're looking for a start, go for "beautiful maladies", it's a collection of his 80's-90's stuff. his older stuff, i'd say go for "closing time" or "the heart of saturday night", or "nighthawks at the diner".