My earliest exposure to Tom Waits was in the 1970s, when I saw him on television performing “Step Right Up.” He struck me as an obnoxious hipster, and I paid little attention to him for many years.

Then, in 1990, I was browsing through the used CDs at Tower Records and came across Waits’ “Franks Wild Years,” as well as No. 12. I was in the midst of getting over a bad period in my life, and something about “Franks” appealed to my dark side. I hadn’t heard any of the songs. Maybe I had read something about it.

It proved to be a smart decision. “Franks Wild Years,” which came out in 1987, was the soundtrack for a play that disappeared not long after its debut. It features outrageous percussion, a pump organ that sounds like something you’d hear on a 1930s radio drama, accordion, sound effects (including a rooster that, as I later learned, turns up on just about every Waits album) and Waits’ otherworldly singing, with seemingly a different voice for every song. Waits wrote every song either solo or with a collaborator; his wife, Kathleen Brennan, shares credits on three and Gary Cohen on one.

At the time that I first listened to “Franks,” I was also reading William Kennedy’s “Ironweed.” There was a certain synchronicity between the boozy losers whose personae Waits adopted and those whom Kennedy wrote about. Waits truly inhabits his characters. He’s also a hopeless romantic, and songs like “Innocent When You Dream,” “Franks Theme” and “Train Song” are suffused with depth and humanity.

After that, I picked up a few more Waits albums. I remember that, sometime in the mid-1990s, WRKO Radio was bringing in guest hosts on Sundays, and I got the call one week. They asked me what I wanted for bumper music. They told me I could pick anything within reason — not, you know, Tom Waits, ha ha. Well, as a matter of fact … I asked for the instrumental that opens “Goin’ Out West,” from “Bone Machine” (1992). It’s pretty straightforward, so I got my way.

And may I just say that “Georgia Lee,” from “Mule Variations” (1999), is probably the most heart-breaking song I’ve ever heard. The bridge will bring you to your knees.

Talk about this post on Facebook.