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Five Tom Waits Songs You Should Have in Your Collection

Tom Waits is a musician who defies classification. Equal parts jazz, blues, rock and roll, bourbon bottle, and junkyard cat, his music pushes the limits of popular song forms and orchestration while remaining earnest, heartfelt, raw, and accessible. Why, then, have so many fans still not discovered the treasure trove of wonderful music in this man's extensive catalog?

Since his debut album, Closing Time, in 1973, Waits has released album after album of critically acclaimed music, picked up a few Grammy awards, and made a name for himself as one of the greatest songwriters of his generation, if not the rock and roll era. His songs have been covered by dozens of artists, not least of which Bruce Springsteen and the Eagles, and he collaborates with giants like Les Claypool and Keith Richards on a regular basis. Any fan of music should have some Tom Waits in their collection and these five songs are an excellent starter course into a strange but fulfilling dive into his catalog.

I Hope That I Don't Fall In Love With You

Taken from his debut album, I Hope That I Don't Fall In Love With You is beautiful, simple, folky, heartbreaking, and sweet. At its core, it's a sweet love song about a man trying to talk himself out of falling for a girl he just saw in a bar but the subtext is so heartbreaking and sad that the listener is left wondering whether they should root for love or for these two people to go their separate ways.

Waits' voice, although gravely, is still beautiful at this point in his career and his vocal delivery is so brutally honest that no listener could be convinced that this isn't a 100% true, biographical story song.

Tom Traubert's Blues (Four Sheets to the Wind in Copenhagen)

By the time of his third album, Small Change, in 1976, Tom Waits' voice was beginning to become difficult to listen to. That said, there is still a brutal honesty and sensitivity in songs such as this one which takes a page from the Great American Songbook if that songbook was written by barroom troubadours following an all night bender.

Clap Hands

By the time of Rain Dogs, Waits had a voice barely recognizable from that of his debut album and the instrumentation of his recordings was decidedly not that of a cocktail lounge singer. Now incorporating various percussion instruments, barely tuned guitars, and a completely unconventional song structure, his songs still have a swing and groove to them. Probably not the best music for a make out session in the back of your car but if you're considering holding up a bank, this might be good wind down music.

Christmas Card From a Hooker in Minneapolis


This song, taken from the album Blue Valentine, is a great example of Tom Waits' uncanny ability to tell a story that has never been told in song form, or outside of a brothel, ever before.

It is worth noting that, still, as his voice gets raspier and more "damaged" sounding, the vocal performances are nothing short of brilliant and poignant.

Better Off Without a Wife

If there was ever an argument for someone who absolutely needed a wife, this anthem against needing a wife would be it. Recorded live in studio for the album Nighthawks at the Diner, this track is a great example of Waits' sardonic sense of humor. Sure, he's singing about not needing a wife but it sounds more like a cry for help than anything. The brilliance of a good songwriter, though, is writing a song with a meaning that can change with every performance.

"She's been married so many times she's got rice marks all over her face". Now that's a line.

This is, of course, hardly a fair representation of Tom Waits' music but for fans looking to ease into a complicated and eclectic catalog, this is, hopefully, a good place to start. Leave your suggestions in the comments below.

Featured Image: Tom Waits Closing Time

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Written by: Tony Frye

Tony Frye is the founder and editor of Hero Habit. He is an avid baseball fan with an unusual knack for remembering pop culture trivia from years before he was born.

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