Before he was a solo artist, Kurt Vile was a founding member of The War on Drugs. The War on Drugs without Kurt went on to make music for people who take long, contemplative walks in national parks. Meanwhile, Vile went solo and started making music for Allies of Drugs—the people who sit on the couch contemplating whether they should take a walk. Across his career, Vile created a distinct lane of hazy, sprawling guitar-driven music. He writes songs that feel like they stretch time itself. His lyrics float between laid-back wisdom and vague observations, always delivered with an effortless cool that makes even his longest songs seem to fly by. His albums range from lo-fi beginnings to full-fledged indie rock epics, but they all orbit around the same easygoing stoner charm.

Let’s rank them.

8. God is Saying This to You (2009)

If a lo-fi folk artist mumbles into a four-track and nobody hears it, does it make a sound? That’s the philosophical quandary of “God is Saying This to You,” an album that feels less like a complete project and more like a collection of soundcheck warmups. That said, there’s a certain charm to its hazy, half-formed sketches; almost like listening to someone work through ideas in real time.

Play it again: “My Best Friends”
Skip it: “White Riffs,” “Overnite KV”

7. Constant Hitmaker (2008)

The title was ironic, and the album kind of knew it. This is Vile’s earliest proper solo release, a lo-fi collage of psych-folk and scrappy, reverb-drenched experiments. It has moments where his style starts to form (“Slow Talkers”) but mostly feels like an artist figuring things out on tape—which is to say, it’s fun but not essential.

Play it again: “Slow Talkers”
Skip it: “American Folded”

6. B’lieve I’m Goin Down… (2015)

This album cemented the version of Kurt Vile that the general public knows best—the spacey, rambling, folk-rock guru who sounds like he just rolled out of a hammock to record. It’s less hazy and psychedelic than his earlier work, leaning into classic folk and country influences. “Pretty Pimpin” became his biggest song, a wry, hypnotic meditation on looking in the mirror, barely recognizing yourself, and not being bothered by what you see. It’s an anthem for existential crisis and low-grade disassociation, and the idea of Vile considering himself reasonably pimpin’ is an irony that only makes the song better. The rest of the album is solid, if occasionally meandering. Still, at its best, it captures Vile at his most listenable.

Play it again: “Pretty Pimpin,” “I’m an Outlaw”
Skip it: “Stand Inside”

5. (watch my moves) (2022)

Vile has always made music that sounds like a long, aimless road trip. “Watch My Moves” fully embraces that aesthetic. It’s his most patient album, which is a nice way of saying some of these songs could end a couple of minutes earlier. “Mount Airy Hill” is one of his most hypnotic tracks, floating along like a lazy afternoon with nothing to do. Meanwhile, “Fo Sho” captures his usual detached, dry humor, built around a phrase only Vile could stretch into a mantra. If you’re looking for the most Kurt Vile-sounding Kurt Vile album, this might be it, even if it lacks the standout tracks of his more ambitious albums.

Play it again: “Mount Airy Hill,” “Fo Sho”
Skip it: “Hey Like a Child”

Honorable Mention: Lotta Sea Lice (2017) (with Courtney Barnett)

Some people hear Kurt Vile and Courtney Barnett’s voices together and think they’ve unlocked the meaning of life. Others hear them and immediately need a nap. This album is exactly what you’d expect from two of indie rock’s most effortlessly cool musicians: loose, conversational songs that sound like a long afternoon spent trading guitar licks and half-finished thoughts. “Fear is Like a Forest” has a hypnotic, rolling rhythm, and “Outta the Woodwork” perfectly fuses their styles. But there are also moments where it sounds like two musicians who forgot they were making an album and just started hanging out.

Play it again: “Fear is Like a Forest,” “Outta the Woodwork”
Skip it: “On Script”

4. Childish Prodigy (2009)

This is the chaotic outlier in Kurt Vile’s catalog… his fuzziest, most garage-rock sounding album. Songs like “Hunchback” and “Freak Train” feel raw and unhinged, like someone plugged Vile’s guitar directly into a broken amplifier and let it rip. The album is loud, distorted, and confrontational but never loses that signature Vile looseness. While he eventually smoothed out his style, “Childish Prodigy” proves he can get loud and weird when he wants to.

Play it again: “Hunchback,” “Freak Train”
Skip it: “Heart Attack”

3. Bottle It In (2018)

This album takes its time, stretching songs into long, looping meditations. The highlight, “Bassackwards,” unravels in slow motion, like someone trying to explain a profound thought while actively forgetting what they were talking about. Meanwhile, “Loading Zones” turns refusing to pay for parking into an anthem—a quintessential Kurt Vile move. This album might be too long for some, but it’s pure, unhurried magic for those in the right headspace.

Play it again: “Bassackwards,” “Loading Zones,” “One Trick Ponies”
Skip it: “Come Again”

2. Smoke Ring for My Halo (2011)

This is the perfect balance of lo-fi introspection and polished indie rock. Vile’s songwriting snaps into focus here, and every track feels like the soundtrack to a quiet existential crisis. “Baby’s Arms” and “Society Is My Friend” showcase his ability to be both profound and totally indifferent at the same time. It’s the first genuinely great Kurt Vile album and the moment he became more than just a scrappy psych-folk artist.

Play it again: “Baby’s Arms,” “Society Is My Friend,” “Jesus Fever”
Skip it: “Peeping Tomboy”

1. Wakin on a Pretty Daze (2013)

If “Smoke Ring for My Halo” refined Kurt Vile’s songwriting, “Wakin on a Pretty Daze” is where he mastered his artistry. It’s sprawling, hypnotic (yes, we know we have used that word a few times already, but it’s the best word for the job. Get off our back), and immersive, the sound of an artist entirely in his element. The title track alone is a 10-minute slow-burn masterpiece, the kind of song you sink into without realizing how much time has passed. That’s the magic of “Wakin on a Pretty Daze”—it loops you into its headspace, making you forget where one song ends and the next begins. Tracks like “Air Bud” and “Goldtone” shimmer with that signature lazy-but-precise Vile charm, where every note feels both casual and deliberate.

This album isn’t in a rush to get anywhere, and that’s precisely why it works. You don’t just listen to “Wakin on a Pretty Daze”—you live in it for a while.

Play it again: “Wakin on a Pretty Day,” “Air Bud,” “Goldtone”
Skip it: Nothing. Just press play and drift away.