The aberrant public perception Tom Waits has crafted for himself is informed primarily by his latter career output. Casual listeners may be surprised to learn he didn’t step off of a boxcar one day, fully formed, and start screaming into a megaphone and banging a rusty oil drum. No, real Tom-heads know he has a softer, even schmaltzy, side, mostly evidenced in his jazz-tinged 1970s records. This switch didn’t happen overnight, but is best characterized as a slow descent into madness.

Here are 10 songs from the Tom Waits cannon that follow his slide from beatnik daddy-o to German-expressionist movie monster.

“Martha” 

Just 23 years old when he released his debut album, “Closing Time” introduced the world to an impressive young songwriter who compensated for his scratchy voice with beautifully crafted, wistful yarns. An absolutely devastating love song about an old man reconnecting with an old flame, “Martha” is one of the more conventional songs in the Tom Waits oeuvre. Yet it’s a love song that Tom uses to not so much tug at your heartstrings but to yank them like he’s trying to start a lawnmower. It sounds like he’s playing an antique piano alone in the back of an empty bar (as evoked by the album cover). I like to picture listeners in 1973 saying, “Wow, this kid’s got a bright future. Can’t wait to see how this whippersnapper’s sound matures throughout his career!”

“Big Joe and Phantom 309” 

Waits’ hepcat persona reaches its zenith on this live-in-studio record, intended to mimic the intimate feel of a jazz club. About half the tracks are Tom simply vibing and yucking it up with the audience. We also discover that this crooner is also a bit of a scoundrel. And horny. So horny in fact that, “The crack of dawn better be careful around me,” he posits in the opening intro. The penultimate track is one of Waits’s only covers, and notably, features Tom’s first foray into the supernatural. This story of a hitchhiker picked up by a ghostly trucker is a harbinger of things to come.

“The Piano Has Been Drinking (Not Me)”

The record where Tom hits werewolf puberty, “Small Change” introduces the characteristic growl we all know and love. In some ways, this album is familiar territory. More songs about diners and seductive women, but he’s also branching into more unconventional directions and exhibits heightened wordplay. “The Piano Has Been Drinking” is one such tune, which humanizes inanimate objects around the crummy bar where the protagonist entertainer suffers through his set, such as a carpet that needs a haircut.

“Whistlin’ Past the Graveyard” 

Okay, things are starting to get spooky. Like many of his songs to this point, it is a hedonistic, braggadocious number, though with a decidedly darker tone. The nighttime in a Tom Waits song used to offer the promise of booze-soaked debauchery. “Whistlin’” offers only menace. He sleeps out by the railroad tracks, chugs the Mississippi, and chases the devil through the corn. “Blue Valentine” introduced a crack in Tom’s persona that would soon grow into a chasm.

“Frank’s Wild Years” 

It’s 1983. We are now crossing the Rubicon. Unmoored, we are floating adrift through murky, uncharted waters. The old Tom is dead. Things are about to get weird.

If it wasn’t obvious by the album title, “Swordfishtrombones” marks a turning point in Waits’ sound. The album features bagpipes, banjo, marimbas, glass harmonica, and as advertised, trombones. This pivot coincided with Waits marrying fellow iconoclast Kathleen Brennan, who encouraged Tom to shake the lounge singer schtick and explore new sonic directions and also become a frequent collaborator. Most people get lame when they get married, but not Tom. Tom just gets weirder. Yet “Frank’s Wild Years” (the song, not the 1987 album of the same name) manages to span the old and the new. The spoken-word lyrics and jazzy accompaniment evoke hipster Tom, but the subject matter, about a man’s psychotic break, is anything but. Tom also solidifies his punk bona fides by name-checking Mickey’s big mouth, which the eponymous Frank guzzles in his car before burning his house to the ground.

Strap in, folks. It’s all goblin mode from here on out.

“Singapore” 

The island nation of Singapore has the world’s second-highest GDP per capita and is one of the “Four Asian Tigers.” A desirable destination for investors and visitors alike, the tourism board is unlikely to ever use this song in an official promotion. This jaunty little number introduces one of Tom’s now familiar songwriting conventions: “Scary place where fucked-up people do weird shit.” The melting pot that is “Singapore” also characterizes “Rain Dogs” as a whole. Though numerous avant-garde elements shine throughout, the album is also grounded in traditional Americana, from country/western to New Orleans jazz. But it’s songs like “Singapore” we have to thank for lines like, “Let marrow bone and cleaver choose while making feet for children’s shoes,” that bounce around your brain while you’re trying to go to bed. Just don’t fall asleep while you’re ashore.

“Earth Died Screaming”

Like “Swordfishtrombones,” “Bone Machine” pretty effectively sums up to the listener what they’re in for. Maybe I’m taking things too literally, but it would not surprise me if Tom actually constructed a bone machine to record “Earth Died Screaming” to achieve that sound. It’s the 90s, Tom, lighten up! Anyway, Waits did something especially weird with this album by winning a Grammy. This is also his first album for which Tom became a straight edge icon by kicking the bottle before recording. Half the guy’s songs up to this point were about booze. What’s he going to do now, sing about normal stuff? Buddy, he’s just getting warmed up.

“What’s He Building?” 

Arguably the most disturbing tune in the Waits songbook, ominous creaks and dings pervade this paranoid dirge about belonging to an HOA. Look, everybody needs a project. So what if the guy’s lawn is dying and has enough formaldehyde to choke a horse? About halfway through the song, it finally clicks that the real monster in this tale is the nosy neighbors. Anybody who’s browsed Nextdoor has seen much worse.

“God’s Away on Business” 

Welp, he finally sold out. Waits went and released two albums in the same year inspired by Weimar-era German cabaret, based on limited-run stage productions in collaboration with Brennan and avant-garde playwright Robert Wilson. You hate to see it. Check out the music video sometime in a well-lit room with friends or loved ones close by.

“Clang Boom Steam” 

Okay, he’s beatboxing now. We sure are a long way from the scatting scoundrel from “Jitterbug Boy.” Apparently bored with constructing bizarre percussion instruments out of scrap metal, Tom decided to turn his golden voice into the entire raucous rhythm section for this album. Real Gone is perhaps the album on which the chimera that is Tom Waits has taken its final form. But who knows? He hasn’t released an album in 12 years, but there’s still time left to surprise us.