I was kind of late to get into Tom Waits. I always knew about him, and definitely respected him, but I think it was his association with Primus that really got me interested (he did vocals on one of their classics, "Tommy The Cat"). I remember reading that Les Claypool said that Tom Waits had an open invitation to join Primus whenever he wanted. A couple of years later, Primus backed Tom on his "Big In Japan" from Mule Variations, his debut for Epitaph's Anti- Records label. That was the first time I bought a Tom Waits album when it came out, and it is still my favorite. I'm not the biggest expert on him, but I can help you if you're just looking to get into his music.
It's a little too easy to divide his career into three phases, one for each record label. But they are three different eras for sure, and also, the labels don't play nicely with each other - so there's no career spanning best-of or box set. So you have to delve into each era of his career separately.
He started out on Elektra's Asylum Records, as a sort of boozy vaudeville crooner influenced by ragtime jazz, the blues and a bit of country. Almost no rock and roll influence at all, he seemed like he fell out of a time machine from a few decades in the past. My favorite albums from this era are his debut, 1973's Closing Time (which has "Ol' 55," one of his few hits) and the followup, 1974's The Heart Of Saturday Night. But if you're looking for a great overview of this era, go for Used Songs 1973-1980.
In his early phase, he was weird. But in the 1980s, when he moved to Island Reocrds and married Kathleen Brennan, still his wife and main collaborator, he got truly bizarre. She turned him on to Captain Beefheart, apparently. The albums during this era take a while to "grow" on you, but you are rewarded for putting in the time to get to know them. I recently listened to his music from this era and was blown away by 1983's Swordfishtrombones, 1985's Rain Dogs and 1987's Frank's Wild Years. After that, he got really really really weird with 1992's Bone Machine, which I really like. 1993's The Black Rider, a writing collaboration with William S. Burroughs and Robert Wilson, has its moments, but I'm not as big of a fan of that one.
That was his last album for quite a while, until he emerged on a new label, Anti- Records, which was an imprint of the punk rock label Epitaph. The label started in 1999, and Tom Waits' Mule Variations was one of their first releases, and he remains on Anti- to this day. As I mentioned, it is probably my favorite Tom Waits album. I love the aforementioned "Big In Japan," as well as "Get Behind The Mule" (recently covered by Booker T. accompanied by The Drive-By Truckers and Neil Young) and "Picture In a Frame" (covered by Willie Nelson) and "Hold On." But the whole album is great. I also love his most recent original album, 2004's Real Gone. Surprisingly, there aren't any compilations from Tom's Anti- years yet, although they did release Orphans, a 3 CD set of rarities and outtakes.
The Onion's A.V. Club recently wrote a piece asking "How Long Does It Take To 'Get' An Album?" in relation to the new Radiohead album, King Of Limbs. I'm not sure how long it takes people to "get" a Tom Waits album, although I do know that Waits isn't for everybody. But I do know that, for those who take the time, it's worth the while.
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