50. A.J. Croce – San Diego Serenade
A.J.’s famous father Jim was topping the charts when Waits was first starting out in the music business. Early Waits songs have parallels to Jim Croce’s work. That time period fascinates A.J. and has inspired him in recent years to record several piano-driven covers of early 70s material.
“San Diego Serenade” is a lovely early ballad in which Waits toys around with an age-old formula: “I never knew X until I knew Y.” It’s all about taking precious things for granted, and the regrets that can bring about. Croce’s cover departs from the original by slowly working in a New Orleans-style backing band. Croce’s tasty arrangement of brass instruments makes the orchestral backing on the original seem completely misguided. Until we get a reissue of The Heart of Saturday Night album without the string sections, this will do nicely. – Tom McDonald
49. Pale Saints – Jersey Girl
“Jersey Girl” is remarkable for any number of reasons. My favorite: It’s like a snapshot taken of a man the minute he falls in love. The overflow of emotions, all of them positive, all of them direct from the heart, can’t help but lift up the listener. The song sounds great in any finery, whether rising from the Bowery or cruising down E Street. In the hands of the Pale Saints, “Jersey Girl” is adrift in a technicolor night-time fog. Every last sha-la-la lifts the listener higher – not a leap, but an ascension. It’s dream-come-true pop, and it’s glorious. – Patrick Robbins
48. Mathilde Santing – Is There Any Way Out of This Dream
Some consider Francis Ford Coppola’s epic 1982 film One From The Heart to be an unmitigated disaster, overly ambitious and a total bomb. There are others who believe it to be an underappreciated, misunderstood neon-lit gem (add me to that starry-eyed list). But when it comes to One From The Heart, there is one thing most humans can agree on: its Tom Waits-composed soundtrack, performed by him and legendary country diva Crystal Gayle, is a slow-burning, heart-squeezing masterpiece. “Is There Any Way Out of This Dream” was originally sung by Gayle and featured a suitably Tom Waits-ian gin-soaked arrangement. In her 1987 version, Dutch singing legend and interpretive master Mathilde Santing takes a more romantic and tentative approach. She slows the slowie down, adds some sweet banjo, and serves up a vocal of ridiculous and extraordinary warmth. – Hope Silverman
47. Gogol Bordello & Les Claypool – I’ll Be Gone
In 2008, gypsy-punk band Gogol Bordello and Primus bassist Les Claypool took the Bonaroo stage at around 2 AM for what was billed as a late-night “superjam.” The entire set was made up of Tom Waits covers. Claypool has played bass for Tom himself, so was well equipped to mine the catalog for lesser-knowns and deep cuts. Among the many setlist highlights (“16 Shells” with an “Eruption” tease, Metallica guitarist Kirk Hammett coming over after his band finished their headlining set to shred on a few songs) was this version of a Franks Wild Years cut so deep that, according to setlist.fm, not only has Tom never played it – no one else has ever played it either. – Ray Padgett
46. Mary Coughlan – Lucky Day
Mary Coughlan has one of those voices that could sing the Dow Jones Industrial Average and make it sound sexy, her broad Irish drawl always lingering over every syllable available, and often more. She completely changes the mood of this song, giving it a real Basement Tapes ambience, in a whole different form of ramshackle chaos from the original. The clang clang of the guitar and the organ clash gloriously with the near-spoken-word section. In other hands, it could have just sounded laughable, like a lift from some Nashville train wreck, yet Coughlan just about keeps it hanging on in there. – Seuras Og
45. Holly Cole – I Don’t Wanna Grow Up
The original version of “I Don’t Wanna Grow Up” is manic, grizzled, weird, and oddly ebullient at the same time. So is its accompanying video, starring Tom as a bike-riding satanic wild child in a single red pump. But strip away all the aforementioned fabulous craziness and the song becomes a shockingly different beast.
On Holly Cole’s 1995 Waits tribute album Temptation, she turns the song upside down, shaking out all its innards until there is nothing left but a bass ‘n’ piano skeleton. She then plants a breathy, lowdown, rapturously raspy vocal on top completely turning the wondrous circus of a song into a quietly defiant tear-jerking manifesto. The effect is revelatory. – Hope Silverman
44. Suisse-Marocain – Big in Japan
The original of this track is certainly Waits at his most distorted. There are effects everywhere in this song, from the vocal to the growly guitar and gritty drums. How refreshing, then, that this version cleans things up to the point that almost makes it toe-tapping. With a double bass pulling double duty as the melody line and percussive elements, Suisse-Marocain’s vocal is powerful, crisp, and damn near sultry. It’s a wonder this cover hasn’t been spread wider than its current reach; it’s a beaut. – Brendan Shanahan
43. Puddles Pity Party – On the Nickel
“Tom Waits music is near and dear to me,” says Puddles the Clown. He’s not joking – he has multiple Waits covers on his YouTube channel. One of them is “On the Nickel,” from Waits’ Heartattack and Vine album. Backed by a tack piano (“which clearly had been drinking,” he adds), Puddles is clearly in touch with the song’s pain. It makes you wonder – no, it makes you believe that he was one of those runaway boys who found the world getting too big for him, and found his own down-and-out world where he could isolate without being entirely alone. – Patrick Robbins
42. Southside Johnny With La Bamba’s Big Band – Tango Till They’re Sore
Sometimes bigger is better. The cover itself is quite straightforward, but with the backing of the La Bamba Big Band, Southside Johnny’s version has the punchy depth to fill up your speakers. Waits’ version is perfect for your small-town Louisiana speakeasy, but we’re hitting the back row in the ballroom with this cover, with flourishes from the brass section, a troublesome harmonica, and a showman’s style vocal. – Brendan Shanahan
41. Elvis Costello – Innocent When You Dream
Elvis Costello and Waits go way back and have always been very much in tune with each other. But you’d probably be right to worry about Costello’s 1992 cover of “Innocent When You Dream.” How could the English singer-songwriter possibly work that waltz song without the defining features of raucous vocal, accordion, wonky piano, and hissy/worn-out sound effects, as variably witnessed on the two versions (“78” and “barroom”) on Franks Wild Years. Turns out, though, that Costello really savored and foregrounded the melody and lyrics on the track, because, it must be said, Waits’ beautiful melodies and poignant lyrics are sometimes a little overshadowed in the whole Waitsian mix.
With just Pete Thomas on drum brushes, and Paul Riley on bass, Elvis slows things down and puts no filter on his emotional vocals and self-harmonies, which tease out all the hurt and torment in this heartfelt song about the need to find solace in dreams. Find it on the 2004 expanded edition of Kojak Variety, a collection of covers on which Costello places Waits firmly in the songwriting tradition of Van Morrison, Dylan, Lennon/McCartney, Springsteen, and Gershwin. As you would. – Adam Mason