Tom Waits seemed to arrive fully formed straight out of a Jack Kerouac novel. He was an eccentric beat poet who wrote gin-soaked piano ballads before turning his attention to incorporating avant-garde elements into his musical short stories. All of these things, against the odds, only helped grow his reputation, and Tom Waits is rightfully viewed as one of the greatest rock artists of all time.

The discography of Tom Waits is an amazing thing, with each record feeling more like dense mini-novels rather than assembled pop singles.

Even the true greats have career highlights, moments that jump out more than all others. These are the 10 best songs by Tom Waits.

Top 10 Greatest Songs by Tom Waits

10. “I Hope That I Don’t Fall In Love With You”

You’ll find plenty of edge to Tom Waits ‘ songs once you dip into his catalogue. You’ll also find more than a few baffling moments that contain a strange allure.

His first album is none of that. For one thing, his Jungle Book-ready, Captain Beefheart-inspired growl is not yet present. For another, some of the songs have a pleasing country vibe. This meant that bands like Eagles could cover Waits’ songs and, in this way, keep him paying his bills while venturing toward more interesting territory.

“I Hope That I Don’t Fall In Love With You” is a beautiful country ballad about an inevitable love affair. There’s humour and honesty to this. And it proved that Waits was a writer of great promise.

9. “Downtown Train”

Rod Stewart might sing about being sexy and about hot legs in his own songs. But the former singer for Faces has near-perfect taste when it comes to taking on covers.

It was a poppy Stewart cover that turned “Downtown Train” into Tom Waits’ most popular song (for a while). Of course, the version located on the Americans’ “Rain Dogs” record is more interesting and less radio-friendly.

A kind of ragged Springsteen-like track about catching the attention of someone for just a brief moment, “Downtown Train” deserves its recognition.

8. “(Looking For) The Heart Of Saturday Night”

Tom Waits was a poet first. He was in love with Allen Ginsberg, Lawrence Ferlinghetti and, of course, Jack Kerouac and Bob Dylan. But he was also smart enough to know that he had arrived a few years too late to the party.

Luckily, Waits also possessed an incredible ear and almost virtuoso-like ability on the piano. “(Looking For) The Heart Of Saturday Night” was one of the first times he entertained his poetic instincts on record, delivering, essentially, a poem inspired by post-party melancholy, a farewell to the good times. The song is set over a jazzy instrumental and is one of Waits’ best.

7. “Burma Shave”

Tom Waits ventured deeper and with more control into stranger territory with each release. That’s why by 1977, as typical crooners were struggling against the emergence of punk, Waits was very much in his own world. “Foreign Affairs” sounded like a record that could’ve been recorded in the late 1940s.

The most impressive composition of that time is the short story set to music of “Burma Shave.” Cleverly nicking the title from billboards advertising shaving cream and adding perfectly believable characters to the tale, Waits delivers a song that only he could have written.

6. ‘Wrong Side Of The Road”

There are plenty of unconventional sounds that Tom Waits has used on recordings. Of all of them, none is stranger-sounding or more distinctive than his voice.

An exaggerated blues howl taken into operatic territory, the force of that singing can be best enjoyed on songs like “Wrong Side of the Road.” On this tune, Waits gathers all bad deeds and superstitions together to create his most rebellious composition.

Everyone else was looking for a smooth highway, but Waits and very like him were doing their travelling through the ditch.

5. “In The Neighborhood”

The records of Tom Waits, much like those of The Replacements or the original gangsta rappers, dealt with characters ignored by songwriters and by society at large.

On the other hand, Waits feels most at ease when finding himself in chaotic circumstances and in places where order does not yet reign.

“In The Neighborhood” is a pencil-drawn map of the lives of ordinary people who’ve, nearly all, reached the end of their rope. The memorable video shows Tom Waits leading a procession of misfits through the dirty streets. It’s the best depiction of Waits as a rock star.

4. “Romeo Is Bleeding”

Waits was also a comedian at heart. The “Nighthawks at the Diner” record proved it. But, then again, so do a lot of his more musically adventurous compositions.

“Romeo Is Bleeding” may be a story song about a young gangster who guns policemen just for fun. But as Romeo climbs onto the balcony to watch James Cagney on the screen, you can hear that Waits, as opposed to Springsgreen, sees the grim irony in everything that his characters do.

3. “Telephone Call From Istanbul”

In a truly wonderful story, drummer extraordinary Brain Mantia, who also played with Guns n’ Roses and Primus, described Waits’ meticulous approach to creating percussion sounds. He remembers that on one tour, Waits had purchased one metal wheel. The wheel would be hit precisely one time during the entire show. It was, however, as Waits saw, vital to the integrity of that show.

Rhythm has always played a major role in the music of Tom Waits. In their way, Waits and his live band make larger-than-life, evil-sounding boogie rock. “Telephone Call from Istanbul” should be enough to establish that. And, the best way to enjoy it is through the “Big Time” live album (and theatrical performance).

2. “Tom Traubert’s Blues (Four Sheets To The Wind)”

Tom Waits always looked capable of writing classics. He was always a songwriter of incredible calibre. You could imagine Frank Sinatra or Dean Martin performing one of his songs.

Waits was also known for his persona as a drunken poet, a prince of late-night bohemia. He wrote plenty of songs about booze. And he often seemed the best person to sing them.

There are few greater classics than “Tom Traubert’s Blues.” It’s a song fit for ol’ Frank, but also fit for the nocturnal shouts of a drunkard. The performance Waits delivers is truly affecting as well. It’s a wonderful moment in the history of recorded music.

1. “Clap Hands”

There are 3-4 Bob Dylan albums that all people interested in pop music should own. Similarly, there are three bizarre Tom Waits albums that everyone should own. The albums that I’d strongly recommend investing make up a trilogy of stories. Those records are “Swordfishtrombones,” “Rain Dogs,” and “Frank’s Wild Years.”

You can’t beat those records! But you can’t exactly expect to like or understand them on your first listen. Waits dramatically altered his sound for these. He created wonderfully eerie soundscapes through old instruments and found everyday items. The music feels like it should belong to the soundtrack of a German expressionist movie.

However, the song that should act as the gateway is “Clap Hands.” Powered by a hypnotic rhythm and with singing that seems to belong to some Central American witch doctor, “Clap Hands” is, in my opinion, the shining moment in the discography of Tom Waits and one of the greatest songs ever recorded.