I’m a huge fan of both Waits (my favorite singer-songwriter; finally saw him live last summer!) and Bukowski (my favorite poet). Lyrically, they both share a lot of common ground, particularly earlier Waits: the boozy, bluesy beatnik, the bourbon-chugging skid row philosopher and late-night raconteur of diners and strip clubs.
Since Waits has gone through three pretty distinct career phases, I always recommend the albums Nighthawks at the Diner and *Small Change * as most indicative of his early years (the ‘70s), where the influences of urban jazz, beat poetry, and Bukowski in particular were a lot more evident in his work. You really can’t go wrong with either of those. Most people agree, however, that the highlight of Waits’ career was the trilogy of albums he released in the ‘80s: Swordfishtrombones, Rain Dogs, and *Frank’s Wild Years * (the first two moreso than the latter). I don’t like Waits’ most recent material as much as his older stuff, but that means I simply love it rather than loving the hell out of it. 2004’s *Real Gone * is a pretty good introduction to his more modern, more dissonant, harsher music.
Oh, and Love Is a Dog From Hell is probably my favorite collection of Bukowski’s poetry, although I admit I haven’t read them all yet. I really need to sit down and read Pulp one of these days, his satire of hardboiled detective fiction. Mmmm, I just came back from the City Lights bookstore in San Francisco (an old hangout of Kerouac, Ferlinghetti, and the other Beats), and they have an entire section devoted to Bukowski’s works.