Lost in the Grooves is a bi-weekly column where we revisit overlooked, underappreciated, and downright strange entries in artists’ back catalogues.

I don’t know where to begin with Tom Waits. I tried comparing his music to blindfolded tap dancing, theoretical physics and black holes. I attempted diving into the lineage of American songwriting and Brechtian theatre, all to no avail. No matter how much I tried, the breadth of Waits’ music couldn’t be contained in a trite metaphor.

Even just giving a straight biography of the man doesn’t quite do enough to explain Waits’ mystique. So, let me just give it to you straight:

Have you ever wondered what it might sound like if Cookie Monster came from an alternate-universe version of “Sesame Street” plagued by drug addiction, populated by sex workers, corrupt cops, run-down freak shows, and haunted turntables playing blues 45s so scratched and warped, only the sorrow behind the words is left audible?

If you’re a sick freak like me and said “yes,” then Tom Waits is for you.

He’s an artist with DNA ranging anywhere from the blues and beat poetry to circus music, gospel, and Tin Pan Alley. With each album, Waits further flourished and refined his sound and persona. The jump from boozy bar balladeer to deranged carny to experimental blues musician is jarring from afar, but take the journey with him, and you have a rare example of an artist who, no matter where you jump in, is at their most perfectly realized.

What undoubtedly makes Waits’ music both unique and utterly polarizing is his voice. Since his first album, “Closing Time,” in 1973, his singing was a little gruff, but he could more than hold a tune. Fast forward three years, and, yeah, maybe lay off the cigarettes, Tom. Then, eight years later, and forget the voice, what am I even listening to?

Well, what if I told you that in 2004, Waits got interested in hip-hop? And that the resulting album, “Real Gone,” absolutely rules?

Now, before anyone gets their hopes up: no, it is not an entire album of Waits’ raspily rhyming along to 404 drum beats. While the entire record is hip-hop inspired—filled with samples and Waits beatboxing—it’s actually a diverse blend of blues, Cuban dance music, spoken-word, rock and soulful ballads.

Also, I’ll be referring to the remastered version of the album, which contains completely different mixes from the original release. Both are great, but I prefer the remastered version.

In the Tom Waits canon, “Real Gone” appears directly after “Mule Variations,” his RIAA-certified gold-selling album that remains one of the best-selling and most critically acclaimed records of his career, which also introduced his more blues-oriented sound that would dominate the next decade of his music.¹

The album was born from Waits recording himself beatboxing on a small tape machine. He wanted to use these recordings as the basis of the album and add bare-bones, simple instrumentation to fill out the record’s sound.

“Most of it was written a cappella. I started with these mouth rhythms, making my own cycles and playing along with them,” said Waits in a 2004 interview with Magnet Magazine. “‘Real Gone’ is definitely not a record filled with bizarre, left-wing sound sources. The idea was to go in and do something that was going to be bread and water, skin and bones, three-legged tables, rudimentary three-minute songs. That was the idea.”

The result is by far Waits’ most ramshackle-sounding album yet. Still, “skin and bones” isn’t the term I’d use to describe the combination of Waits’ howling voice, his son Casey’s drumming and turntable work, Marc Ribot’s feedback-ridden “hair-on-fire” guitar playing, and backing-band Primus’s instrumental support.

The songs most unique to the album are the ones clearly inspired by hip-hop, and happen to be the most straightforward, like “Top of the Hill,” the first track on the record, possibly about what a body sees on its way to the cemetery.

It’s a perfect opener that reinstates Waits’ penchant for the macabre that permeates all of his music, but mixed with the groove and Waits booming “Hey!” and other ad-libbed lines that pop up throughout, it feels almost like a wink to the camera—a gesture that grounds a theatricality that could otherwise derail and defocus the album.

The rest of the album is filled out by what Waits does best: story songs and tone poems. Waits is arguably rock and roll’s best storyteller. His songs feel like intimate tours through the ghostly remains of small-time criminals and Americana-infused Shakespearean tragedies.

“Sins of My Father” is a ten-and-a-half-minute walk with generational guilt. Waits speaks with just enough ambiguity about what exactly the narrator and his family are accused of, and lets the listener fill in the gaps. It results in a far more powerful song, where the blood on the hands of Waits’ protagonist slowly oozes through the speakers until Waits deftly denies you the satisfaction of finding out what his character must do to wash their hands clean.

“Night is falling like a bloody axe / Lies and rumors and the wind at my back / Hand on the wheel and gravel on the road / Will the pawn shop sell me back what I sold?”

“Don’t Go Into That Barn” was inspired by The New York Times article, “In A Barn, A Piece of Slavery’s Hidden Past,” about the discovery of the remains of a slave jail in a barn in Kentucky. The song combines real lines from the article with relentless, pounding percussion; the result is an eerie campfire story rooted in the still-present, violent history of America.

The final track on the record, “Day After Tomorrow,” is an emotional gut punch.² The most reminiscent of Waits’ earlier work, the song is from the perspective of a soldier dreaming of returning from the Iraq War. Waits has always been and would continue to be both slyly and overtly political, but “Day After Tomorrow” is a howl of pain, a call for humanity and a reminder of the people caught in the grand designs of politicians.

“How does God choose? / Whose prayers does he refuse? / Who turns the wheel, who throws the dice? / On the Day After Tomorrow / I am not fighting for justice / I’m not fighting for freedom / I’m fighting for my life / And another day in the world here.”

If you can’t tell, as it is with every album by Waits, “Real Gone” is dense, and I’ve only touched on less than half of the tracklist. I didn’t get to mention the brash anti-war blues of “Hoist That Rag,” the spoken word interlude describing the residents and performers of a nightmare carnival on “Circus,” the sinister romance of “Green Grass,” or the demented dance instructional “Metropolitan Glide.”

It also probably became very clear, very quickly, if “Real Gone” and Tom Waits as a whole is your thing. He is a tough pill to swallow, and even on my own odyssey through his bizarre world, I’ve questioned more than once why I’m putting myself through this and if I even like any of the music in the first place.

But again and again, I’m called back to his strange worlds and their seedy inhabitants, and I’m rewarded for sticking around. For the few who decide to take the plunge, settle in and be patient. Waits is not a tourist in his dark mirror world; he knows where the locals hang out, and every detour and digression is more than worth it.

1. His 2002 albums, “Blood Money” and “Alice,” are collections of music Waits wrote for two operas by Robert Wilson, not brand-new studio albums.

2. “Chick A Boom” is a run-out groove/hidden track.