Happy Tuesday, folks! It’s August now, and I have to go back to work next week. Boo. In the meantime, I’ve been listening to a lot of Tom Waits the past couple of days. I figure he’s got several modes, or characters, that he plays in his songs: there’s the junkyard carnival barker, full of weird friends and weirder situations; there’s the jazzy hipster who read Kerouac a few too many times and always wears a damn trilby, regardless of whether it goes with his outfit or not; and there’s the hopeless romantic crooner, sitting at his piano and crying softly into his beer. That last one is the one I’ve been focusing on, and here’s ten of his best.

1. “(Looking for) The Heart of Saturday Night”: As good an ode to driving the main drag with your best girl in the seat by your side as any Bruce Springsteen ever wrote. But, whereas the Boss’s odes to the road are always desperate, hopeful paeans to escape and freedom, Tom Waits’ version seems more subdued, more realistic. Monday’s gonna come back around all too soon, so you might as well enjoy the drive and the pool hall while you can.
2. “I Hope That I Don’t Fall in Love With You”: Early tune (from his debut, Closing Time) lamenting how easy it is to fall in infatuation with someone at first sight, and how often such things go disastrously wrong (at least for Tom).
3. “Tom Traubert’s Blues”: It feels like the cinematic opener for some stage musical. Ane the chorus lifts directly from the old song “Waltzing Matilda” to gorgeous effect.
4. Shiver Me Timbers”: Who knew a song about being a pirate could be so affecting?
5. “Christmas Card from a Hooker in Minneapolis”: The best fake-out in musical history: she’s not married, there is no baby, she’s actually in jail and needs to borrow money. Brutal and heartbreaking.
6. “Hold On”: Probably one of the more optimistic songs in Tom Waits’s catalog.
7. “Ol’ 55”: Let’s just forget the Eagles’ cover of this one. It doesn’t have a patch on the original ode to a car.
8. “Jersey Girl”: The best Bruce Springsteen song he never wrote, to the point that folks often think it is a Bruce song and he’s even covered it live on several occasions.
9. “No One Knows I’m Gone”: A dark meditation on being alone and unnoticed.
10. “Please Call Me, Baby”: A simple love song, which Waits can drop in the middle of all the carnival japery and found-instrument weirdness like it’s no big deal. Y’know, just a perfect encapsulation of a relationship from out of nowhere, like you do.