The Best Kurt Vile Songs, Ranked

For nearly 20 years, Kurt Vile has been one of the most reliable names in indie rock. His latest album, Philadelphia’s Been Good To Me, adds to a career where the pride of Pennsylvania has regularly produced off-kilter, idiosyncratic but always ingratiating “lo-fi, DIY rock ‘n’ roll,” to quote his recent single “Chance To Bleed.” In that time, he’s often been compared to Neil Young and Tom Petty, and for his generation, he’s been a similarly consistent presence, supplying a lifetime supply of backyard jams that are endlessly replayable. Here are 10 of the best ones.

10. “It’s Alright” (2011)

If you know Kurt Vile’s music, you’re aware that certain words have multiple meanings. “Yeah” is one of those words. He might mean “yeah” like “yeeeeeah,” an expression of affirmation. Or he might mean “yeah” like “yeeeeeah,” which belies some inner dissatisfaction he’s signifying counterintuitively. The nuances are real, and they are (indeed) extremely nuanced. And then there’s “alright,” another of Kurt’s pet words. In “It’s Alright,” “alright” does not mean “alright” the way you and I mean it. It nods more in the “inner dissatisfaction” direction, which you get from the context of the music, all foreboding distortion and aching existential moans.

9. “He’s Alright” (2009)

In this song, however, “alright” is closer to the regular meaning of “alright.” (We also get one of his greatest all-time “yeahs” in the chorus.) In “He’s Alright,” he’s more or less articulating the Tao Of Kurt, where you might “grab the bull by the horns” one moment and use up all your cash on records the next. Such is the duality of man, the very multitudes contained within that Walt Whitman (and Bob Dylan) have talked about. But Kurt refuses to be moved by any of it. “Sometimes I think getting older is, oh, so last year,” Kurt drawls. And then he says “I don’t care” nine times in a row. Why? Because eight times would have been too few.

8. “Freak Train” (2009)

The biggest misconception about Kurt is that he’s a slacker. It’s an image the man himself plays up, of course. But his work ethic contradicts the stereotype. And then there’s the proactive nature of the music itself. Forward motion is a constant in his songs. Life is a journey, as is the typical Kurt Vile song, which tends to chart the path — at various speeds, though not often “rapid” — from point A to point B, spiritually speaking. And then there’s “Freak Train,” which literalizes that onward propulsion in the form of an (uncharacteristically) furious chugga-chugga rhythm and Kurt’s own manic vocal. Live, you know a Kurt show is going to another level if this one comes out toward the end.

7. “Freeway” (2008)

Another testament to Vile’s blue-collar, hard-working appeal is the way he got started in the music business. In the Philadelphia area, he was known as “the CD-R guy,” a prolific songwriter who would record his latest songs, burn them onto blank discs, and then distribute them for free at shows. Over time, he built up a local following. He was known in the area, as Dave Hartley of The War On Drugs later told me, as “this long-haired, really funny, strange guy hanging around with these little CD-Rs.” Of course, he would be known only as a Philly-based eccentric if he didn’t also have the goods in the “non-stop bangers” department. Vile actually called his proper 2008 debut Constant Hitmaker, and he wasn’t joking, especially when it came to the breakout song, the Tom Petty-like “Freeway.”

6. “On Tour” (2011)

In interviews and elsewhere, Neil Young is a constant point of reference for Kurt Vile. They share many attributes, including a proclivity for long guitar solos and a casual mastery of chunky rock songs that deliver satisfying, endlessly durable hooks without seeming to make much of a big deal about it. With “On Tour,” Kurt once again gestured to Neil, this time to Young’s legendary “ditch” period in the mid-1970s, when he frequently wrote insider accounts about the dark side of rock ‘n’ roll. Kurt’s own exposé is about the rigors of life on the road, a classic subject for a rock song, which he likens to Lord Of The Flies over a doleful folk-rock strum that feels like missing home after being away for too long.

5. “Pretty Pimpin’” (2015)

The most important attribute that Kurt shares with his hero Neil Young is the ability to mix the serious with the silly as if they were one and the same. Kurt often front-loads a goofy, happy-go-lucky vibe, but it’s usually a Trojan horse for smuggling feelings that are deeper and more devastating. Tonally, this can be jarring, since most songwriters aren’t comfortable being funny in their songs (or even making themselves the butt of the joke). But for Kurt, this unique amalgam has produced some of his greatest songs, starting with “Pretty Pimpin’.” Ostensibly a feel-good stoner jam, the song has a lot more going on beneath the surface, with Kurt looking at himself in the mirror and not recognizing the person he sees, the very definition of profound psychological displacement. Though Kurt’s crooked-smile delivery disarms whatever pretensions might normally accompany a phrase like “psychological displacement.”

4. “Girl Called Alex” (2013)

Sometimes, Kurt wears the angst in his music on his sleeve. One of his best songs in that regard is “Girl Called Alex,” a gorgeous mid-tempo number where he lets his mind drift and linger on a girl he once knew. “Thinking about a girl” is one of the oldest tropes for a rock song, but “Girl Called Alex” is more thoughtful and interior than most. Listening to it actually feels like getting lost in a memory, as the wobbly but indelible guitar riff and the draggy rhythm section slowly get lost along with Kurt murmuring within his own sweetly melancholic reverie. At one point, Kurt stops himself mid-sentence (“I wanna —”) before allowing himself a short but expressive guitar solo.

3. “Baby’s Arms” (2011)

An underrated aspect of Vile’s music is just how romantic it can be. Unlike most long-haired record-collecting nerds, Vile has a real tender “lover man” side that comes out in songs like “Baby’s Arms.” A delicate, finger-picked folk song, “Baby’s Arms” is also an unvarnished love ballad, with Kurt singing with earnest gratitude about his baby’s arms, hands, and everything else. It’s where he can hide when he’s sick of everyone, but also where he can restore himself to full strength after being drained by the rest of the world. It’s the track in the Kurt Vile oeuvre most likely to be picked as a wedding song, preferably as groom baby and bride baby are holding each other in their arms.

2. “Jesus Fever” (2011)

The platonic ideal of a Kurt Vile song you can play one million times and never tire of. The sort of quality that Neil Young and Tom Petty exhibit over and over. In terms of modern indie-rock songwriters, Kurt is a master of this form of impossibly solid rock songwriting. As is custom with this kind of tune, it doesn’t seem terribly complicated. Just a straight-forward strum and a lightly choogling rhythm section, followed by Vile’s laconic vocal about feeling “already gone” as he heads back on another adventure. A sweet guitar solo, naturally, closes things out, but by then you’re already itching to press the arrow back to the beginning.

1. “Wakin On A Pretty Day” (2013)

When Kurt sat down to make this song, I wonder if he thought, “Jesus Fever” was cool, what if I just made it longer? If that was his thinking, it was a brilliant idea. “Wakin On A Pretty Day” fits all the contours of a perfect Kurt Vile earworm, but it just gives you more of what you want from him. Around this time, Kurt became the rarest of contemporary beasts — a genuine guitar hero. His solos on “Wakin On A Pretty Day” might not be technically brilliant, but they hit you right in the heart, extending the song’s hypnotic spell without weighing it down. The resulting nine-and-a-half-minute track never feels like nine and a half minutes. Rather, it’s like a walk in the spring sunshine, a pleasurably mellow trip you never want to end.