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.

Around the time the band was writing this album, they also recorded a couple of tracks for HBO’s hit fantasy series “Game of Thrones.” They were pretty good, especially when the guy from Snow Patrol did a cameo to sing one of them. Anyway, this album came out a few years later and has songs on it.
The first album to not include contributions from Franz Nicolay, a 19th-century toy soldier who came to life to play keyboards, “Heaven is Whenever” is noticeably more reliant on the diminishing quality of Tad Kubler’s guitar riffs. While it’s not terrible by any means, if someone says this is their favorite Hold Steady album, it’s time to make an excuse and stop the Tinder convo.
Pretty much every Hold Steady album is an excuse/reason for Craig Finn to write some short stories about drug-addled losers and set them to some kickass chug-rock. Now that everyone in the band is middle-aged, it’s more relatable than ever and even a bit boring. Just like all of us, really.
If a band can make it nearly 20 years before a brass section become a big part of their sound, it’s probably a good thing. This album is pretty full of horns, but not the worst thing they’ve ever done, so it’s quite a pleasant surprise. Call it the “Can’t Hardly Wait” exception.
Sometimes an iconic band will hit a second wind deep into their career and produce a classic, like the Rolling Stones’ “Some Girls” or Neil Young every couple of years or so. This is probably the closest the Hold Steady will get, full of weird sonic grooves and odd song structures that would have been unthinkable to the band 15 years earlier. Plus, Franz Nicolay is back, so there’s the pointy mustache factor.
A band’s debut album should be the template for their career and “Almost Killed Me” fucking rocks that shit. The album introduces many of the motifs Craig Finn would return to again and again, namely near-death experiences, the sad sweetness of getting wasted with people you don’t even really like, and a pair of scuzzballs named Halleluiah and Charlemagne. The band would soon perfect the formula, but it’s probably easier when it begins near-perfect.
Craig Finn has said “Stay Positive” is about aging gracefully, which shows how far back the band was preparing to become elder statesmen of indie rock. The album is the band just a moment past their creative zenith, which makes for some of the most fascinating music of their career and a great album to listen to while slamming a PBR.
The band’s only true concept album, “Separation Sunday” details the life of Halleluiah (Holly, to her friends) in elusive and evocative detail. While Holly is referenced through the discography of the band, their second album is a full, agonizing portrait of a young woman burdened by addiction and hard living, yet full of an inextinguishable radiance, set to the finest riffs they would ever produce. We’d make a joke, but we’re having too many feelings just thinking about it.
The Hold Steady broke out of the constraints of Springsteen anthems and Hüsker Dü attitude with this one, and we can only say “fuck yeah.” This is the kind of album that makes you feel like there’s a point to poetry, rock n’ roll can save your life, and maybe angels exist in a shitty bar at closing time. See? Listen to it enough, and you start talking like Craig Finn.











Inspired by frontman Anthony Raneri’s split from his wife & move to Nashville, “Vacancy” is by far Bayside’s most personal album. We’re all for artists being honest and vulnerable, but this one kind of makes you feel like you’re sitting in divorce court with Raneri and his ex-wife without being paid a lawyer’s rate. It didn’t affect our ranking, but Raneri’s ex did try and bribe us to put this one last, which we think speaks well to its content.
The New York punk & emo scene was alive and well in the early 2000s, and Bayside’s 2004 debut album made it clear that they were on their way to becoming the next big thing. Not everyone was all in on them at the time, but if you were one of the people talking shit about Raneri’s voice, you have either come to love it, or you are still wrong and your opinion doesn’t matter.
Coming off of two highly acclaimed albums, “Shudder” is like when the gifted kid in class gets a C+ instead of an A. Given their reputation you know it’s just a weird fluke and they’re likely going to bounce back, but that doesn’t mean people aren’t going to make a huge deal out of it until they do. And, spoiler alert, they did indeed bounce back.
Bayside’s latest full-length features, arguably, their best guitar work to date. “Interrobang” is loaded with fun, fast tunes that’ll have even the old heads jumping around at shows. Well, maybe not. If you were into the band since the beginning your knees may not be able to handle that now. It might not be a bad idea to get yourself some PT though, because Bayside doesn’t appear to be going away any time soon.
“Cult” clarified that Bayside was indeed growing and changing, which was a bold move by a band whose fan base, for the most part, wasn’t doing either. The band was settling into a more mature sound instrumentally, while still writing lyrics perfect for break-up-fueled away messages, even though AOL Instant Messenger hadn’t been a thing for several years by this point.
Bayside’s third studio album showed the world that they had one thing that a lot of bands trying to make it in this genre did not have, and that is musicianship. They could write sad teenage anthems and they could play their instruments, like, really well. This release quickly launched the band into a much bigger spotlight. Even your high school bully who listened to butt rock knew the words to “Duality.”
It seemed like everyone was killing time at the start of the decade. Whether you were wishing away the semester, the work day, or your crush’s relationship, we all couldn’t wait for the summer and the Warped Tour, “Killing Time” gave everyone something to get stoked on. Bayside were far from burning out, which is more than we could say for our friends (and ourselves) at the time.
Go ahead and tell us we need to grow up. Accuse us of ranking on nostalgia. Write “She’s not coming back, bro” in the comments. We don’t care. Bayside’s 2005 self-titled album is forty minutes of no-skip anthems that continue to stand the test of time. Put yourself in a room of a thousand people in their thirties and forties screaming the words to “Don’t Call Me Peanut” and try telling us the world isn’t full of melancholic beauty. But seriously, all sappy shit aside, this album is quintessential Bayside in every conceivable way.