10 Best Tom Waits Songs Of All Time

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Tom Waits has spent more than five decades turning late-night loneliness, broken characters, strange humor, and battered beauty into one of the most distinctive catalogs in American music. These ten songs trace that journey from the piano ballads of his early years to the theatrical, percussive, and wildly imaginative work that followed.

Feature Photo: English: Published by Asylum Records. Photographer uncredited and unknown., Public domain, via Wikimedia Commons

I first got into Tom Waits while I was in high school during the 1970s. A friend of mine played me a song called “Warm Beer and Cold Women.” Just the title alone is going to make you drop everything and take a listen. I was a huge Springsteen fan at the time, but there was something different about Waits. This dude was much darker, funnier, and as genuine as they come. He did not take anything seriously but somehow took it more seriously than most. I have been a fan since I purchased my first Tom Waits album, Nighthawks at the Diner, after hearing that live song.

What I have loved about Tom Waits over the years has been his commitment to the arts, never staying the same and always evolving as an artist and as a human being. The man understands the definition of the word art. I love his earliest piano ballad-style songs through his 1980s circus-style, horror-sounding arrangements, while always throwing in one of those old-time ballads in between.

I have covered his music many times and written articles like Top 10 Tom Waits Songs of the ’70s, ’80s, and ’90s. I just thought it was time to do an all-time top 10, because why not? It is fun to do, and I will probably change my mind about this list tomorrow, but for now, in this moment, these are my top 10 best Tom Waits songs of all time.

# 10 – “Martha”

I wanted to open this list with something from his first album. Closing Time stands as one of my favorite Tom Waits records of all time. When you listen to this record and then listen to an album like Swordfishtrombones, you will think they are by two different artists, which is what I love about Waits. Nonetheless, “Martha” is the ultimate one-that-got-away song. It is sad, it is beautiful, and it hurts to listen to because we all have that one person with whom we wish we had done something differently.

# 9 – “Somewhere”

I caught myself as I began to write about this song when I was just about to say that Blue Valentine is one of my favorite Tom Waits albums of all time. It seems that I may be saying this about every single song and album I have included here. I am a big fan; I cannot help it. But of course, Blue Valentine is definitely one of my favorite Tom Waits albums, if not my favorite. Now, of course, we all know that this is not a Tom Waits original; it is one of the most famous songs ever recorded for the silver screen and Broadway. It is a stunning piece of music written by Leonard Bernstein and Stephen Sondheim. Many fans of the play and movie West Side Story might be taken aback when they hear Waits perform this song, but that is what I love about it. Waits takes this piece of music, those tender, painful lyrics, and makes them more genuine than I have ever heard them before.

# 8 – “Step Right Up”

On this song from the Small Change album, released in 1976, we started to get a peek at the direction Tom Waits would eventually head in during the 1980s. That circus-like atmosphere and the cinematic qualities he brings to music are all brewing in this one. I wonder if he even knew where he was heading because I think he just got there organically.

# 7 – “Downtown Train”

I can already hear some readers frowning at this pick because it was a big hit. Sadly, sometimes music fans of a particular artist do not like the songs that become hits because they feel betrayed in some way, as if they are no longer the only people who love this artist. I get it, I understand it, but in the end, this is a fantastic song. Of course, Waits did not really have the hit; Rod Stewart did, and I actually like both versions. I mean, how could you not like Rod Stewart’s version? Rod Stewart is simply one of the greatest singers of all time. But of course, Waits’ version is his own, and the video is spectacular.

# 6 – “Bad as Me”

“Bad as Me” stands as the title track of the last released Tom Waits studio album, Bad as Me, released in 2011. It is hard to believe that it has been almost 15 years since Tom Waits released new music, or at least a new studio album. I am not sure whether we will ever get new music from him again, but I hope we do. This one continues with the style of music he began in the early 1980s with Swordfishtrombones. There are some simple ballads on here, but the majority of the record sounds like the title track, which is simply fabulous. Waits sounds completely out of his mind on this one, which was obviously the point. He is pretty bad, which is actually pretty good.

# 5 – “In the Neighborhood”

There has always been a cinematic quality to Tom Waits’ music. Still, it is how Tom Waits has taken his observations of everyday life, of the ordinary and, of course, the sometimes not-so-ordinary, and woven them into stories in his music that has made his songs so relatable to so many of us. On this album, in which he changed his style completely, there were still some remnants of his old music, and this one was the perfect blend of the old Tom Waits meeting the new Tom Waits. It was, in many ways, the ideal album closer, leaving us all wondering where he would go next.

# 4 – “What’s He Building?”

Every line in this song, if you want to call it a song, is priceless. “He has subscriptions to those magazines.” I mean, come on, how can you not love that line? His lawn is dying. Maybe the words do not jump out at you in print, but his delivery deserves some sort of award, although I just do not know what type. If you have never heard this, you need to hear it now. Waits may have hit his artistic peak on the album Mule Variations. This was genius. And of course, that whistling at the end just seals it.

# 3 – “I Hope I Don’t Fall in Love with You”

This song, “I Hope I Don’t Fall in Love with You,” has, hands down, the best closing line I have ever heard. It is what makes this song so special. It is the ultimate lesson in never hesitating. This is the second song we have picked for this list from his debut album, Closing Time.

# 2 – “Christmas Card from a Hooker in Minneapolis”

Well, we just mentioned how the song “I Hope I Don’t Fall in Love with You” has one of the best closing lines of all time. This one comes pretty close, too, although it is more than just a line; it is a stanza. It is another adventure in how he takes an entire song, sets a scene so magnificently, and throws you a curveball at the end that makes complete sense in every single way. It is the truth that lies so evidently at the end, the genuine artistic notions that Waits always put at the forefront of his music, that makes him one of the most loved songwriters of all time. Another great one from our favorite Tom Waits album, Blue Valentine. There you go, I said it, our favorite Tom Waits album.

# 1 – “Ruby’s Arms”

I can never really pick which part of Tom Waits’ career I like the most, his early days filled with some of the most beautiful piano-written songs, his carnival-style circus rock and roll, or whatever you want to call it. I think in the end it comes down to individual songs because I love all aspects of his career. Picking my number one song by Waits was not an easy task, but this one has always hit me hard. It is just so magnificently beautiful, and if you have never heard it, this one will leave you breathless. It is from the Heartattack and Vine album, which was pretty much his last album in the old Tom Waits style before he crossed over into Swordfishtrombones territory.