“I said, ‘What about Keith Richards?’ I was just joking... He came with about 600 guitars in a semi-truck. And a butler”: How Tom Waits began a decades-long creative partnership with the Rolling Stones legend

On its surface, a Tom Waits/Keith Richards collaboration – let alone multiple, stretching across decades – seems a bit improbable.

Though beloved by critics and his ever-loyal cult following, Waits' ramshackle, straight-from-the-underbelly poetry has found its largest audiences through the voices of others.

The propulsive, perfect-for-the-mid-'80s rocker Downtown Train reached the upper echelons of the charts via Rod Stewart; Ol'55 came through the turntables of millions after the Eagles covered it for their On the Border album, while the imperial ballad Jersey Girl became so often misattributed to Bruce Springsteen that the Boss made it part of his own onstage repertoire.

And yet, why wouldn't the singer/songwriter best known for his singular, gravelly, whiskey-soaked vocals – time-weathered even when he was barely 30 – click with the wizened rhythm guitar master who's lived a thousand lives with the world's greatest rock and roll band?

Seeing their potential musical and personal chemistry, Waits' wife and musical partner, Kathleen Brennan, encouraged him to seek Richards out during the making of his masterful 1985 album, Rain Dogs.

Waits himself thought the team-up was about as likely as winning the lottery, but nevertheless decided to name the Stones legend – as a joke, mind you – when his record company asked if he wanted guests on the album.

What do they say about speaking things into existence?

Tom Waits - "Downtown Train" - YouTube

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Recalling the chain of events in a 2011 interview with Pitchfork, Waits recounted, “My wife Kathleen said, ‘Why don't you get Keith Richards on here? You love him. You love what he does. We're in New York and he lives in New York.’ And I go, ‘Oh, I gotta listen to this shit.’

“So then I was talking to the record company and they say, ‘Any guests you want on the record?’ And I said, ‘What about Keith Richards?’ I was just joking, but somebody went ahead and called him. And then he said, ‘Yeah.’ And I said, ‘Now we're really in trouble.’”

Now, Richards is known to be far more of a down-to-earth presence than his tabloid perennial bandmate Mick Jagger, but this is still a Stone we're talking about.

“I was really nervous. He came with about 600 guitars in a semi-truck. And a butler,” Waits said of the guitarist's arrival.

“We were in these huge studios in New York, like The Poseidon Adventure. Huge, high ceilings in these rooms like football fields. They'd fill these things up with orchestras and we were in there with five guys. It felt a little weird. He killed me. I was really knocked out that he played on all those things.”

By “all those things” Waits means a whole trio of Rain Dogs cuts, most prominently the lolling Blind Love, to which Keef lends the twangier side of his lick library, and backing vocals.

Tom Waits - "Blind Love" - YouTube

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Richards has gone on to appear on two more Waits albums – co-writing and playing on That Feel, the closing tune from 1992's acclaimed Bone Machine, and either lending licks or vocals to more than a third of the tunes on Waits' most recent LP, 2011's Bad as Me.

Speaking about his recording experiences with Waits in a 2023 Uncut interview, Richards said, “The sessions I do with him, it’s just him and me.

“He has a unique angle on just about everything, and it’s refreshing to hang around with him and join in. We kick around every subject under the sun and then we get in front of the microphone and do something.

“Tom’s music is so American. Probably more folk-American than anything, but somehow modern. He’s a weird mixture of stuff – a great bunch of guys!”