"Chicago"

'Bad As Me', 2011

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Does “Chicago” have the best horn part of any Tom Waits song? Hard to beat those staccato blasts propelling the song from the first second, with the low tuba groaning through a moment later. Two members of the Preservation Hall Jazz Band (who Tom had collaborated with on their own album one year earlier) handled the horns: Clint Maedgen on sax and Pres Hall leader Ben Jaffe, subject of an interesting recent New York Times Magazine feature, on trombone, bass clarinet, and tuba.

Plus, it’s not technically a horn (I know, I know, neither is a clarinet), but Charlie Musselwhite adds some steam-whistle harmonica to the end while Tom hollers “All aboard!”

Sadly, Tom’s never played the song live with the full horn section it deserves. A rendition with the Preservation Hall frontline would be a hell of a thing. Having not properly toured since Bad As Me came out, he’s only played “Chicago” twice period. The first time, promoting the album on Letterman, offers an alternate arrangement of sorts, driven far more by the guitars than by the sole sax player:

For the second performance, at his one-off Bridge School Benefit appearance in 2013, he added a second horn. The sax-trombone combo comes closer to recreating the album’s windy cacophony. The horns take over the harmonica’s “All aboard” part at the end too while Tom vamps. He’s also moved over to piano, rather than just singing like on Letterman, standing up to pound along like he’s Jerry Lee Lewis.