Tom Waits should appear an interesting figure to almost anyone. You know who he is, you've seen him in movies, his songs have been (some would say unfortunately) popularized by
Spingsteen ("Jersey Girl"), Rod Stewart ("Downtown Train"), and the Eagles ("
Ol55"). You're perfectly aware of him... A perpetually old, perpetually hat-wearing pathological liar, who, after returning to music from a 7-year stretch without an album, told every single interviewer who asked what took him so long: "I was stuck in traffic." But there's STILL a wall around the music itself. It's almost like a big inside joke, because you can't just pick up a record and get into his music.
First of all, there are 20 records between 1973 and today. Ignore the "gravelly voice" thing for now, everyone either gets over it or comes to appreciate it. The first thing to do is provide some chronological context, so you know which end of the spectrum you're in if you decide to listen. Between 1973's
Closing Time and 1980's
Heartattack And Vine, you have genuine bar sleaze, foraying into the seedy underbellies of jazz and blues. Most recommended from this era is 1976's
Small Change, including "The Piano Has Been Drinking (Not Me)" and "Invitation To The Blues."
In 1983, Waits was pushed into experimental territory in a reversal of the usual paradigm: by sobering up and settling down with wife/faceless collaborator, Kathleen Brennan (to whom he's still married today).
Swordfishtrombones was the first of a trilogy of albums, followed by
Rain Dogs and
Franks Wild Years. Check out "Gun Street Girl," the linguistic evolution of traditional few-strings-short-of-a-guitar blues. "Jockey Full Of Bourbon," "Hang On St. Christopher," and the title track to
Swordfishtrombones are other easier-access highlights of the era. After this came
Bone Machine, which won a
grammy for Best "Alternative" Rock performance, to which Waits responded, "Alternative to what?" The song "
Goin' Out West" is most memorable for its appearance in Fight Club, definitely the peak of Waits'
growly rock songs.
OK, now, a little soundtrack work, stage productions, and 7 years later we arrive at 1999's
Mule Variations. Lots of people like it, I'm not sure about it. More
folky than Waits' older work. Next we have two albums released at the same time...
Alice. From Robert Wilson's experimental twist on
Alice In Wonderland, which figured into its stage context the fact that Lewis Carroll wrote his Alice stories for the eponymous 9-year-old girl who had captured his affections. Listen to the title track, and that's about it. Now this is important: if you only listen to one Tom Waits song, listen to "All The World Is Green" from
Blood Money. The album has plenty to offer in between its less accessible
pieces, but this is, above all, the doorway to Tom Waits. Then from 2004's
Real Gone: "Dead And Lovely" and "Green Grass" are most recommended.
So now that you've gotten your bearings, hopefully you can appreciate the rest of the catalog.
Admittedly, nothing is truly accessible, but there is a certain difference between Tom Waits and many other performers. With most, even if you can't get into it at first, there may be a moment when it all clicks and you understand it. With Tom Waits, these things click very gradually... Maybe first it's the lyrics, which lead you to appreciate the voice... Maybe then it's the more traditionally-constructed songs from
Small Change or
Blue Valentines, and by the time the 80's records roll around into your music collection, you see the transition and understand those a little better, and then you come to understand the more folk-oriented records coming from Waits' growing domesticity.
Before you know it, you'll be bothering your coworkers or your wife or whoever comes into the room with music they probably won't like. I dunno, though, I always liked that feeling.