Top 10 Tom Waits Songs

Written on March 8th, 2026 by Dr Hobo

Tom Waits is one of those artists you either stumble into or get handed by someone who loves you. There’s no mainstream route in. His early records are late-night piano ballads soaked in cigarette smoke and unrequited love — and then somewhere around Swordfishtrombones he threw the whole thing in the air and rebuilt it from junkyard parts. Waits has always written about the people on the edge: the drifters, the drunks, the hopelessly romantic, the quietly broken. Nobody does it with more tenderness or more wit. These are my ten favourites. As of March 2026.

Downtown Train

Album: Rain Dogs Year: 1985

Hold On

Album: Mule Variations Year: 1999

Time

Album: Rain Dogs Year: 1985

Martha

Album: Closing Time Year: 1973

Ol’ 55

Album: Closing Time Year: 1973

Jersey Girl

Album: Heartattack and Vine Year: 1980

San Diego Serenade

Album: The Heart of Saturday Night Year: 1974

Shiver Me Timbers

Album: The Heart of Saturday Night Year: 1974

On the Nickel

Album: Heartattack and Vine Year: 1980

Hope I Don’t Fall in Love with You

Album: The Early Years Vol. 2 Year: 1973

Honourable Mentions

These almost made the list, and on another day, some of them might have:

(Looking For) The Heart of Saturday Night — The Heart of Saturday Night, 1974
Come On Up to the House — Mule Variations, 1999
Cold Cold Ground — Franks Wild Years, 1987
Christmas Card from a Hooker in Minneapolis — Blue Valentine, 1978
The Piano Has Been Drinking (Not Me) — Small Change, 1976
Tom Traubert’s Blues — Small Change, 1976

What are your favourite Tom Waits songs? Drop a comment and let me know what I’m missing.