Long John

A little bit of a cheat with this Sketch Friday because even though it is indeed a sketch, it was drawn back at the end of 2025. I just never got around to sharing it, unfortunately.

Building on an exercise I started with Sketch Fridays #94, a portrait of Hilary Swank, I have occasionally dipped back into the exercise of drawing a likeness from a photo to keep my skills of observation as honed as possible.

Tom Waits is a musician I’ve been enamored with for years, since first being introduced to him back in 2002 by a coworker. I ended up getting two of his albums in a very short span; first is the delicate, austere, and masterful 1973 debut, Closing Time, where he was very much playing the role of bourbon-fueled jazz club pianist sloppily wrapping up a long gig. By the second song on the album, “I Hope That I Don’t Fall in Love With You,” I was a convert and wanted to inject this music directly into my veins. I was surprised by how normal it was considering all I had encountered from him before was his gruff and wild music videos from Mule Variations and when he popped up as an actor every now and then. The songs on his debut are beautiful, expertly crafted, and hauntingly powerful.

But then I wanted to get into the weird of Tom Waits, to hopefully see how he went from what I heard in Closing Time to the current Tom Waits. So, I was recommended Rain Dogs and though while it was not his firs “weird” album, it was definitely part of the trilogy that got that version of Tom Waits going. And I loved it. The third song on that album, “Cemetery Polka,” made me a convert to this mode of Waits and I wanted to inject this music directly into my veins.Not instead of Closing Time and not in spite of it, but in addition to it. The funny thing is that as wild and cacophonous and experimental as Rain Dogs––or any of his modern work––gets, the gentle, focused, crafted, Tom Waits is still there, popping up with incredibly normal but powerful songs in the midst of all the zaniness.

I mentioned years ago that I started a habit where I pick a musician I always said I was a fan of and decide to actually put it to the test by buying and listening to their entire discography one at a time, chronologically. That way I can say I’m actually a fan instead of just a fan of a single or one album I happened to pick up.

This started in 2019 with Queen, and I’ve been through a handful of other artists since then. The most recent musician I catalogued was Tom Waits and it was quite the trip. As is always the case, I don’t love every album, and some albums I pay closer attention to than others, but having followed his professional journey from beginning to end, I can’t deny the impact such an experience had on me.

I’m definitely not saying that everyone should go out and listen to his music––from beginning to end his work can be an acquired taste––but if anyone ever got curious and came to me asking for a recommendation, I know that I could find an album in his discography that suits the fancy of any type of music fan.