For whatever reason, this 2023 list was the most difficult I’ve ever put together. And yet, it was also the easiest list for me to write. That might be because it’s also not a very adventurous list – it mainly features artists and genres I’ve written about in the past – but maybe it’s because the appeal of these songs is so apparent that I feel like I didn’t have to explain them too much. Either way, I hope you forgive me for my blind spots, and accept this list for what it is – one man’s opinion, and a guide to help you discover some music you might as well. With all of that in mind, please enjoy The Postrider’s Top 20 Songs of 2023 (Read Part 1 here).

10. “all-american bitch” – Olivia Rodrigo

You know that scene at the end of Kill Bill Vol. 2 where Bill talks about how, contrary to popular interpretation, Clark Kent is Superman’s disguise, and not the other way around? I imagine something similar was going through Olivia Rodrigo’s mind when she sat down to write “all-american bitch,” the soft-heavy-soft opener of GUTS, her sophomore full-length album. The picture perfect Disney image was just a front, she seems to suggest, this Veruca Salt shit is the real me. Maybe, as an almost 30-year-old rooting for rock to return to mainstream relevance, I’m the perfect mark for this kind of thing, but the reason it feels more effective than similar child-star-gone-bad gambits (Miley Cyrus, Demi Lovato, etc) is because Rodrigo isn’t necessarily looking to be treated like an adult. Instead, she’s content to be the pissed off, jaded 20-year-old she really is – or as she might put it, “I know my age and I act like it.” No moment in the song better encapsulates this attitude than the careening turn toward the bridge, where Rodrigo eschews another acoustic verse in favor of an eye-rolling send up of platitudinal optimism and composure. She may not be the second coming of Courtney Love, but thank god she’s bringing some sneer back to top 40.

9. “Knockin (Single Version)” – MJ Lenderman

Ask ChatGPT to write the opening line to an MJ Lenderman song, and it might come up with something like “We saw John Daly sing ‘Knockin’ on Heaven’s Door.’” But while an AI program might be able to play the [dirtbag ex-athlete] sings [iconic classic rock song] Mad Lib, there’s no it could infuse such goofy imagery with the same bittersweet tenderness as Lenderman, and certainly no way they could recreate his J-Mascis-by-way-of-Asheville ax work. Like most Lenderman songs, “Knockin” is a melange of the ridiculous, the pathetic, and the sublime, an ode to the kind of love that endures even after a judge takes away your driver’s license and you have to lean on your partner in more way than one. Is the climatic invocation of Bob Dylan’s anthem a sign that the narrator has reached the end of his life, or a higher plane of peace? Drink like John Daly, and the two might become tough to tell apart. 

8. “Not Strong Enough” – boygenius 

I’ve gone on the record about my disappointment in, uh, the record that sad girl supergroup boygenius’ first full-length album was. It felt like it never quite made the most of its trio’s powers. At least part of that disappointment stems from the fact that so few of that album’s tracks reach the heights of “Not Strong Enough,” in which Lucy Dacus, Phoebe Bridgers, and Julien Baker feel like they finally become one to create the kind of speeding-down-the-highway single that used to rocket groups to the top of the pop charts. Its exhausted attempts at escapism feel like the apex of a certain kind of millennial ambition, one in which the narrators would be able to start a new life if not for their crushing anxiety and doubt. Each singer gets a verse to explore their particular wheelhouse – Bridgers’ despair, Baker’s classical American iconography, Dacus’ wrestling with the supernatural and the divine – as well as a chance to come together for the instant classic chorus and supernova bridge. Boygenius may have doubts about their individual abilities to overcome their own limitations, but together, they find power in their flawed humanity. 

7. “Chosen to Deserve” – Wednesday 

Their various musical talents aside, perhaps the biggest service Asheville, North Carolina’s Wednesday provided the indie rock world with in 2023 was a reminder that the genre used to be regional, reflecting the tastes and idiosyncrasies not just of cultural hubs like New York and Los Angeles but Midwestern and Southern cities like Minneapolis and Athens, Georgia. “Chosen to Deserve” furthers this cause not only through its country-indebted arrangement, but also its stark but winking treatment of adolescent drug abuse, a topic that’s so often glamorized in music and sensationalized in film and television. Wednesday vocalist Karly Hartzman isn’t doing E at raves and loft parties – instead, she’s slugging Benadryl and stealing her parents liquor, right before hooking up in her boyfriend’s SUV and going off to teach Sunday school. Dangerous and embarrassing as these stories may be, Hartzman doesn’t look back at them in shame. Instead, they’re merely completed chapters in her life, necessary steps she had to take in her two-horse home town to eventually end up in the arms of her lover. And they let her write this song, too, so they couldn’t have all been bad.

6. “Tom Petty’s gone (but tell him i asked for him)” – Kurt Vile 

Kurt Vile’s spacey psych-folk jams usually come with a broad sense of c’est la vie, but “Tom Petty’s gone (but tell him i asked for him)” is markedly mournful and anxious, a lament for connections lost and never made, and a plea to soldier on. In comteplating the overdose death of Petty, the suicide of David Berman, and the fragile mortality of Bob Dylan, Vile wonders how he’ll ever be able to cope with the cruel and corrupt world we find ourselves living in, especially if two of these three legends couldn’t make it themselves. But for all of his angst, Vile’s biggest regret seems to be that his fallen friends aren’t able to see the light side like he is, and that if they’d only focused on the yang instead of the yin, he wouldn’t have to search across dimensions to find them. It’s not quite survivor’s guilt, but it’s still a recognition that a world he once knew is slowly slipping away, and the only way for him to keep it alive is to lose himself in the sound.

5. “Time Ain’t Accidental” – Jess Williamson 

There’s something oddly classy and grown up about the combination of drum machines, saxophone, and acoustic guitars on “Time Ain’t Accidental” and the way it harkens back to an era where even the country singers were experimenting with synths, gated snares, and other musical innovations of the 80s. That mature sound enhances the intense but tempered love affair described by Jess Williamson. These aren’t two kids – they’re adults who’ve been around the block before, and who are trying to luxuriate in every moment of this phase in their relationship because they know it won’t last forever. They know the timing of this fling may not be accidental, but that also means its end won’t be, either – best to pour yourself another drink by the pool and try to enjoy the moment, no matter how fragile it may be.

4. “Bath County” – Wednesday 

Wednesday may have songs that are more descriptive and detailed than “Bath County,” but no image in the Karly Hartzman songbook matches “We joined the Exodus”/”Headed out from Dollywood” in its brilliant mix of Biblical grandeur and trailer trash reality, and few songs in the band’s catalog feature as pure a display of their unique musical dynamic. Building slowly with that Southern gothic scene, the band slowly picks up pace as Hartzman witnesses a resurrection via Narcan, a vision that’s so revelatory it leads her to spin down the highway, blasting Drive-By Truckers songs and screaming her love for her boyfriend and bandmate, Jake “MJ” Lenderman, while the band responds with squalls of feedback gnarly enough to strip the paint off of a car. It’s an invigorating statement of purpose from the band – about their influences, their environment, and their fraught Southern heritage – and one that’ll be held up the way they hold up the music of their heroes many years hence. 

3. “A&W” – Lana Del Rey

In my review of Did you know that there’s a tunnel under Ocean Blvd, I asked whether or not “A&W,” the album’s seven-minute centerpiece, represented a conceptual dead end for Lana Del Rey, an admission that she’ll never stop singing about, in her words, “the experience of being an American whore.” Maybe it does – but it also acts as the pinnacle of a type of Lana Del Rey song, the most complete realization of the 21st Century film noir femme fatale character she’s been cultivating for over a decade now. The first half of the song is the kind of wispy piano-based ballad we’ve come to expect at this point in her career, but it tumbles along at a deliberate pace as she details her various indiscretions and how empty they leave her, only to revert to the “gangsta Nancy Sinatra”-type hip-hop she made her name off of early in her career, mockingly teasing her lover while puffing on cocaine-laced cigarettes. It tempts one to ask: is the real Lana Del Rey the tragic figure of the first half, or the sly, uber-confident temptress of the second half? The point of the song is that it’s both, and that Del Rey’s career has in large part been devoted to breaking down these essentialist divisions between the used and the user, much in the same way that she bridges the generation gap with her 50s rock references and millennial slang. As I said in my album review, I don’t know how long she can keep going back to that well. But it’s working for now, and in 2023, it resulted in one of the best songs of her career. 

2. “Black Earth, WI” – Ratboys

If you’ve followed my writing for a few years, it probably won’t surprise you to see “Black Earth, WI” high up on this list. Like “I Know the End” and “Bull Believer” before it, it’s a five-and-a-half minute-plus indie rock song with a long instrumental break and a clear climax. But unlike those songs, “Black Earth, WI” isn’t rooted in fear, angst, or exasperation. Instead, it’s built on top of an inviting Sean Neumann bassline that sets the stage for Julia Steiner’s always comforting voice. Steiner’s lyrics aren’t free of frightful imagery, but the lightning strikes on Lake Michigan and blinding yellow lights feel more like signs from beyond than tool of the impending apocalypse, and even David Sagan’s long, searching guitar solo turns into a chanting singalong, a build up to a communal moment rather than a display of individual chops. Instead of ending on one massive crash, Ratboys ride out on Neumann’s bass again, as Steiner slips into a half-lullaby while the rest of her band asks “does that black dirt freak you out?” Even if it does, Ratboys are right next to us, holding our hand, letting us know it’ll all be ok.

1. “For You to Sing” – Mo Troper

When I saw Mo Troper live earlier this year, he talked about a recording studio in his native Portland, Oregon that charged bargain-rate prices and sported the slogan “community, not competition.” In protest, he wrote “For You to Sing,” a song about “crushing the competition.” 

Spite, jealousy, and vindictiveness have been the inspiration for many great pop songs, so it’s no surprise that Troper, one of the most biting and subversive songwriters of his era, was able to take those feelings and channel them into an innocent sounding power-pop single. But for all of its talk of control freaks and Svengalis, “For You to Sing” also stands out in its tenderness. At the root of this possessiveness is a desire to be loved, a desire that curdles into petty toxicity the second Troper sees whoever he’s addressing sing someone else’s tune. It’s a feeling we’ve all felt before, even if we would never admit to it. That Troper was able to stuff it into such a catchy, sugary package, and make it the kind of song you want to listen to again and again, is enough to make it the best song of the year.