Way Down in the Hole

Originally Performed ByTom Waits
Original AlbumFranks Wild Years (1987)
Music/LyricsWaits
VocalsTrey
HistorianParker Harrington (tmwsiy)
Last Update2026-01-03

History

“Way Down in the Hole” was first performed by Phish on August 2, 2017, opening Night 10 of The Baker’s Dozen at Madison Square Garden, a show themed around donut holes. Fans arriving at the venue were handed donut holes dusted with peanut butter chocolate dust.

Originally written by Tom Waits and released on his 1987 album Franks Wild Years, the song is best known to many listeners as the opening theme to The Wire, where shifting versions framed each season’s story arcs around systemic decay and the blurred lines between order and chaos. A decidedly Phish-like notion.

Frequently cited as one of the greatest television theme songs of all time, “Way Down in the Hole” achieved an unusual cultural afterlife through The Wire. Each season featured a different interpretation, most notably by Steve Earle, Blind Boys of Alabama, and The Neville Brothers. Ironically, Waits himself has rarely performed the song live, a scarcity that only deepens its mystique given how widely recognized it has become.

Fifteen years before The Wire, “Way Down in the Hole” appeared in a Tom Waits stage production he created with his wife, Kathleen Brennan, at Chicago’s famed Steppenwolf Theatre based on the album Franks Wild Years, which was subtitled "Un Operachi Romantico in Two Acts.” The show had a short run and never reached Broadway, but the song had already found its footing. So while the play itself, a surreal story following the downward spiral of a disillusioned accordion player, may have largely faded into theatrical history, the song it birthed will never be forgotten.

Footage from the documentary "Big Time" of 1988 combined in a new edit with the audio from the album from the documentary. Video by Strangels

Phish, as they often did throughout the Baker’s Dozen run, showed an uncanny instinct for not only matching song choice to theme and place but also to make the choices unexpectedly interesting. Opening the Donut Hole show with the unmistakably site-specific line, “If you walk through the garden / You better watch your back,” immediately cast the room in shadow. That warning would later find its counterweight in the second set with the Phish debut of, “O Holy Night, creating a subtle arc: one song looking downward at temptation and the other reaching upward toward redemption.

Phish played the tune straight, allowing its street-preacher gravity to stand in contrast to the playful absurdity of the Baker’s Dozen theme as a whole. With Trey taking the lead on vocals, he adopted the same deliberate delivery of Waits’ original version. It was anchored by Mike’s thumping bass which provided the rhythmic 'crawl' essential to the song's blues-gospel roots. The performance also included a standout organ solo from Page channeling the energy of the Blind Boys of Alabama version, giving the Garden a momentary transformation into a revival tent. 

Like other Baker’s Dozen one-offs, 'Way Down in the Hole' thus far remains a singular appearance, remembered less for improvisation than for placement and context. It is another example of Phish’s ability to deploy a culturally significant song at precisely the right moment: a one-night-only revival that lingers in the Garden’s rafters, waiting for the next time the band decides to dig deep into the hole.

Last significant update: 1/3/2026

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