Kahan also recently appeared as the musical guest for the May 9 episode of “Saturday Night Live,” hosted by fellow New Englander Matt Damon. This summer, he’s slated to play four shows at Fenway Park on July 7, 8, 10, and 11. All this is to say that there’s no better time to take a deep dive into his back catalogue.
Many of Kahan’s songs have captivated fans, but they’re not all winners. If you have no idea where to start, Boston.com has you covered. For this ranking, I relistened to all 76 of his officially released songs and reviewed each one.
This list includes every track from Kahan’s four studio albums and two EPs, along with a live track and a few singles. Alternate versions, such as remixes, acoustic takes, and the extended cut of “The View Between Villages,” won’t be found here.
Additionally, the only collaborations included are those where Kahan is the primary credited artist. For example, “Hurt Somebody,” a Kahan song featuring Julia Michaels, makes the list; “Sarah’s Place,” a Zach Bryan song featuring Kahan, does not.
Nothing on this list is offensively bad; the weakest songs are mostly just boring. However, “Someone Like You” feels like a feeble attempt to capitalize on the success of “Hurt Somebody,” which wasn’t all that good to begin with. Oladokun tries her best to add something of substance, but her talent is ultimately wasted on bland lyrics and a weak melody.
Pairing sad or dark lyrics with an upbeat instrumental can be really effective if done right. That’s not the case here. “I cried at the rain, but there’s no way that I’m depressed” is a laughably trite way to depict mental illness compared to what Kahan would later write.
The title sums it up — it’s fine, and nothing more.
I listened to every track on this list several times, yet I can’t remember a single line of “Tidal.” It refuses to stick in my mind.
Sharing a name with one of the greatest songs ever written does not a great song make.
The way Kahan sings the chorus almost resembles a Post Malone flow. That goes about as well as you’d expect it to.
Kahan’s label, Republic Records, knew they had a hit on their hands with “Hurt Somebody.” This led to a solo version, a duet with Michaels, and two remixes. What all these versions have in common is that they’re not worth your while.
Not a traditional breakup song. Rather, it’s about a relationship that has fallen apart yet continues on — a topic that Kahan would approach later on in far more interesting ways.
A similar premise to “Caves,” though it’s more one-sided this time. Despite its fairly generic lyrics, it has an edge over other duets because mxmtoon’s voice pairs with Kahan’s a bit better than Michaels’ or Oladokun’s.
Catchy, but the “ooh”s in the chorus quickly get annoying.
Even early on, Kahan was writing about his mental health struggles, but compared to similar efforts on his debut album, “Save Me” feels indistinct.
The line about the 401(k) is corny and the chorus gets repetitive by the end, but it’s honest.
A brief flicker of themes that Kahan would explore more specifically and effectively in later songs.
Starts strong with a great first verse but struggles to keep that momentum going.
Just-okay lyrics with a just-okay instrumental to match.
It all starts here. Kahan’s debut single, like many of his early songs, has solid lyrics but suffers from overproduction. The acoustic take would’ve been a better choice for the “Busyhead” album.
A heartfelt track, but it makes the grave mistake of reminding me that I could be listening to “Father and Son” instead.
Contains a genuine groove and is better for it. The color-coded lyrics aren’t bad either.
A bit messy, but handedly the strongest offering from Kahan’s first EP.
Kahan’s best song not released on an album or EP. A strange decision to pass on this one for the “Busyhead” album in favor of tracks like “Cynic” and “Tidal.”
Kahan has said that “Sink,” which he wrote at age 16 and released on SoundCloud, was the song that landed him a deal with Republic Records. Maybe it’s not a crowning achievement, but it certainly shows the potential they saw.
A pleasant opener to “Cape Elizabeth,” all things considered, but everything that follows it is better.
This track has yet to receive the studio treatment, but it appears on a live album recorded during his first-ever shows at Fenway in July 2024. In that context, “Pain is Cold Water” operates as a prelude of sorts to “Maine.” Not an essential listen, but it has the potential to be if fleshed out.
There are no bad songs on “Stick Season,” so “worst” really means “least good” here. One song inevitably has to hold that title, and my pick here is “No Complaints.” Among the extra songs found on later versions of the album, I feel this one adds the least. It’s fine in isolation, but looking at the bigger picture, it retreads a lot of lyrical ground. Granted, it’s far from the only culprit in that regard, but it’s also musically lacking by comparison, with a barebones arrangement that gives it more of an unreleased demo vibe.
A touching tribute to a friend gone too soon. The references to Jack White and Billy Joel are goofy but endearing, especially with the meta nod to Kahan’s song in the final chorus.
Kahan showed his angrier side on “The Great Divide,” delivering quite a few kiss-off songs. “Dashboard” is the weakest of these, accessing strong emotions but lacking the nuance of stronger tracks like “Willing and Able” and “23.”
“Still” has the opposite problem of “No Complaints.” Whereas the latter fails to stand out alongside the rest of “Stick Season,” the former feels essential for a smooth transition between “Homesick” and “The View Between Villages.” Separated from that context, it’s the least interesting of the 14 songs on the original album.
The verses are pleasant, but the chorus leaves something to be desired. Of the four bonus tracks on the deluxe edition of “The Great Divide,” this one feels the least essential.
I’ll probably catch hell for this, but “Forever” never stuck with me, despite its popularity. I could see it playing over the credits of a movie about Kahan’s life. In other words, it summarizes the themes of “Stick Season” more than it expands them.
The push-and-pull between optimism and realism here hints at the turmoil and hope explored in later acts of “The Great Divide.” The bridge does a particularly good job with this.
The “Stick Season” album showed tremendous growth in several areas of Kahan’s songwriting. This track spotlights his improved skills at pairing bouncy, upbeat instrumentals with anxious lyrics.
The opening track on Kahan’s debut album is one of its stronger efforts. Some questionable production on the post-chorus, but otherwise a solid start.
Feels like an outtake from the “Stick Season” era. That’s not necessarily a bad thing, but there’s less evolution to be found here than in most tracks on “The Great Divide.”
Goes hand-in-hand with “She Calls Me Back.” Everything good to say about that song could also be said about “All My Love,” but the latter has the better lyrics and melody.
Feels like a sobering, melancholy cousin to Death Cab for Cutie’s “I Will Follow You Into the Dark,” and I consider that quite the compliment.
Comes across as a prequel of sorts to “Stick Season,” especially with the exit sign imagery in the first verse. When you get to the chorus, you realize it has all the same low-self-esteem woes.
In typical Kahan fashion, the scenes of lighthouses and shorelines are subverted to show the narrator being left behind rather than escaping. The droning background notes fading in and out like a lighthouse’s beam are a nice touch.
Escapes the misplaced production found all over Kahan’s first two albums. Rather, the strings and choir are used to great effect, infusing this piano ballad with a grandeur reminiscent of early-days Elton John.
The fact that “New Perspective” is this low on the list is a testament to how many quality songs Kahan has written. “The intersection got a Target / And they’re calling it downtown” might be his funniest tongue-in-cheek lyric.
Possibly the most straightforward and confessional exploration of Kahan’s mental health on the “Stick Season” album. I admire the vulnerability, but it’s a bit on-the-nose at times.
Has a hushed intimacy that adds some dynamic range to the latter half of “The Great Divide.” Its only fault in that regard is that other songs just do it better.
I’m of the opinion that an artist’s most popular work is rarely their best, and Kahan is no exception. Lyrically, it’s a mixed bag. For every “might not have, but I did not lose,” there’s a “COVID on the planes.” It’s not hard to see why this was his big hit. It’s simple, catchy, and packs an emotional punch, but separated from that popularity, it doesn’t hold a candle to his very best.
Hints at the consequences of fame on Kahan’s life. The perspectives he chooses to take here are really interesting; unlike how countless others have tackled this topic, he centers these consequences at home rather than on the road. It comes across as a ruthless self-interrogation that’s harder to stomach than songs about loss or longing.
“Kahan’s other biggest hit is similarly overrated,” I say, drawing the ire of thousands of fans. Sorry, but it’s true. Same deal as “Stick Season”: fun, catchy, great hook, but not among his very best.
Even before “Stick Season” exploded his popularity, Kahan was reckoning with the consequences of fame. The result was “Godlight,” one of the few truly memorable and compelling tracks on “I Was/I Am.” It’s the only song from the album that he still plays in concert, and it’s not hard to see why he keeps it around.
After the overture of “End of August,” the opening riff of “Doors” tells listeners that the album’s story is officially beginning. It gives a great sense of movement, even if it shares a bit too much musical DNA with Foo Fighters’ “Everlong.”
An understated, overlooked gem from “Cape Elizabeth.” It’s a nice change of pace to hear Kahan take the role of comforter rather than expressing his own anxieties.
Remember how I said “Save Me” was an indistinct exploration of mental health issues? “Busyhead” is a far better example. Despite being the title track of Kahan’s debut album and the namesake of his nonprofit, it doesn’t seem to get the love it deserves. You’d think that would count for something.
Infuses a bit of country into the primarily folk and pop-oriented “Stick Season.” The clever and yearning but simply stated lyrics definitely help guide this stylistic switch-up.
Probably the most Bostonian track we’ll ever get from Kahan. The Charles River. The Harvard track team. The burning hatred for Logan Airport. It’s all there.
In contrast to the overproduction of the “Busyhead” album, “Cape Elizabeth” is acoustic bliss. Though one song from that EP towers over the rest, “Glue Myself Shut” might be the best example of how it blends breezy melodies with introspective lyricism.
Remains the most enduring track from the “Busyhead” album and keeps a constant spot in Kahan’s concert setlists. It’s arguably the most similar pre-“Stick Season” song to his newer material, both lyrically and musically.
Kahan typically isn’t one to close his albums with sweeping, grandiose exits, and “Dan” really illustrates why that approach works for him. After so many tracks about separation, these fleeting images of togetherness are simultaneously sweet and melancholy.
The two tonal poles of Kahan’s music come together here in a single song. The buildup from the finger-picked, soft-spoken opening verses to the electric, screamed climax is fantastic.
“Halloween” is among the trio of songs on “Stick Season” which I’d call underrated. Sequenced right before “Homesick,” it has a hushed, calm-before-the-storm vibe that I really appreciate. The lyrics have a quaint timelessness to them that you can’t always find in Kahan’s music, and the minimal instrumentation helps them shine.
Another angry song from “The Great Divide,” but the rage here is dulled to a simmering bitterness. The strain that Kahan’s fame has put on his “hometown heroes,” as he calls them, is present again, but it’s a subtler statement than “Haircut.”
The title is really a perfect tonesetter. It enhances the circling guitar melody and fish-out-of-water lyrics rather than explaining them. All of these elements deftly illustrate how Kahan’s fame leaves him feeling out-of-place away from home.
One of the anthems of “Stick Season” and a fan-favorite in concert. In keeping with that spirit, it’s an unabashed expression of enduring love which contrasts the fragmented feelings that are more common across the album.
A natural choice for a lead single, and not just because it’s the title track. Thematically, “The Great Divide” tells listeners that the season of the sticks is now long gone. Does that mean Kahan’s lyrics will gain some levity? Well, not exactly, but there’s no denying that this is one of the album’s more optimistic tracks.
With acoustic ballads making up most of “Stick Season,” “Homesick” gives Kahan a chance to rock out and release his pent-up resentment. He doesn’t pull any punches here. The line “I’m mean because I grew up in New England” is a firestarter at any Boston concert.
The energy that “Deny Deny Deny” brings to “The Great Divide” is very similar to what “Homesick” brings to “Stick Season.” However, I think the former is just a bit stronger, mostly for its chorus. Maybe that will piss off my fellow New Englanders, but you know what? Bring it on.
This one hooked me right from its killer opening lines, which may or may not owe something to Bruce Springsteen’s “Atlantic City.” The ambient noise and rough edges give it a raw, off-the-cuff feel that “The Great Divide” could have benefitted from more of. For a fleeting moment, it sounds like Kahan is having a lot of fun.
The second in my self-identified trio of underrated “Stick Season” songs, though this one has gained some momentum with fans in time. Coming off the intensity of “Orange Juice,” its gentleness is disarming. Its lyrics and those of “Halloween” have a similarly timeless quality.
Right from the first song of “Stick Season,” Kahan sends the message that something is different here from his previous work. It comfortably stands alongside “Everywhere, Everything” in the “anthems” category, and for good reason. As a New Englander, this is one of many that hits close to home.
A song so gut-wrenching and personal that Kahan has admitted to struggling to perform it live. I typically love complexity in my lyrics, but this is a prime example of why the simplest approach is sometimes the best. Past a certain point, it’s less about the words themselves and more about how they’re said.
Whereas most songs on “The Great Divide” about Kahan’s friends and family feel charged with anger, “Porch Light” doubles down on sadness. He’s gained so much from his songs and their popularity, but there’s plenty to be lost as well. Considering it’s written from his mother’s perspective, it’s hard not to think that for those who love him, it might feel like a loss only.
The fact that this is on the same album as songs like “Someone Like You” continues to baffle me. After two albums of trying to fit the square peg in the round hole with pop production that just doesn’t suit him, “Howling” shows what Kahan is capable of when left to his own devices. It’s just him, his guitar, and some of his best lyrics. It’s a shame this one seems to have been forgotten about. If there’s any song from “I Was/I Am” worth revisiting, this is it.
On repeat listens, no “Stick Season” song has grown on me more than “Come Over,” and it caps off my aforementioned trio of underrated songs. “I’m in the business of losin’ your interest / And I turn a profit each time that we speak” might be my single favorite set of opening lines in any Kahan song. The pervasive self-consciousness itself isn’t unique to this song, but it’s explored with a charming childhood innocence. It also features some of Kahan’s strongest vocals, and his voice truly soars in the chorus.
The crown jewel of the angrier songs on “The Great Divide.” Whereas “Haircut” is contempt and “Willing and Able” is bitterness, “23” is unbridled rage that sours into disillusioned acceptance. After so many songs where Kahan is begging someone to stay, the chorus of “Stay gone / Won’t you stay gone?” hits that much harder.
One of the sweetest tracks on “The Great Divide.” If this specific ranking tells you anything, it’s that I’m a sucker for Kahan’s more folksy songs. When I picked up my guitar to learn a song from the new album, this is the one that called out to me. The chorus has an almost nursery rhyme quality to it, yet it also perfectly captures the mundanity of adult life. The whole song is like a rainy New England morning.
As a recent college graduate, I admit I may be biased. Add to that the fact that this is the first Kahan song I truly fell in love with, and I accept that I’m definitely biased. But honestly, even after separating myself from those biases, I still think “You’re Gonna Go Far” deserves a spot as one of his best. The themes of feeling stuck throughout “Stick Season” finally get their release with some much-needed hopefulness and optimism. It’s another one of those tracks that works because of how straightforward it is.
Buzzing cicadas and wistful piano runs open “The Great Divide” in what feels like an overture to the album’s story. Compared to the more lowkey closer (see No. 24), “End of August” has a grandeur to it as the track slowly builds. Only one other track from this album tops it, proving how strong of an opener it is.
I’ll go out on a limb and say “Maine” is the first song Kahan ever wrote that will still be considered one of his all-time best years from now. The guitar riff and distant bird calls in the intro anchor the song perfectly, and these lyrics are the first ones that I would truly call timeless. The line about “cameras in the traffic lights” is one of my all-time favorites.
The penultimate song on “The Great Divide” is also its best. All the emotions that the previous songs have dredged up swirl around together on this track. The fingerpicking melody is one of the prettiest Kahan has ever laid down, and it expertly shapes the rising tension across the song. Simply put, it’s simultaneously calming and tragic, and nowhere on the album does Kahan use sonic range better than here.
Across different versions of “Stick Season,” several songs have functioned as its closing track, but “The View Between Villages” is irreplaceable. There’s only three verses to unpack here, but the space between them is crucial to the way they are emphasized. It caps off the album’s themes without summarizing them (see No. 48). Instead, it feels like an emotional release that also features some of Kahan’s best vocals.
No other song had a chance. “Orange Juice” is unquestionably the best thing Kahan has ever released. It’s the centerpiece of “Stick Season,” and nowhere else has his lyricism been so focused yet so raw and vulnerable. There’s ghosts in many of his lyrics, but never do they come out to play quite like they do here. It’s to the point where you can feel them haunting the song itself as the tension builds. Add to that the palpable devastation in Kahan’s voice as he sings, and you have a recipe for the most gut-wrenching, emotionally poignant piece he can call his own.
