By Spencer. If previous writings (such as this, this, this, this, this, or this) haven’t made it clear, Ryan Adams is a longtime favorite on this site. But with a catalog spanning fifteen official solo albums, three Whiskeytown albums, numerous EPs, and probably a dozen more unreleased albums worth of material that you can find in various disreputable corners of the internet, well, he can be an intimidating artist for novices. With so much material to choose from, and so many different sounds to his name, where do you start? That’s where I’m here to help.

I’ve been listening to the man since the beginning. In a way, I think that makes me lucky. I’ve had the chance to digest this music a release at a time, over the course of a decade-and-a-half. Instead of trying to drink from the firehose, I got this music a glass at a time. And what still amazes me, looking back on that kind of a career, is how much of this output is really good. There’s filler, to be sure, but Ryan Adams to date has put out at least six perfect or near-perfect albums, along with another six pretty decent ones. Even the disappointments usually have a handful of killer tracks on them. Only two albums are, in my opinion, absolute duds. (We’ll get to that).

So before I provide you with the obligatory playlist of tracks to get your started in your Ryan Adams education, I’m going to rank those official albums from worst to best. First, a couple of ground rules:

• No EPs. That’s not to say Ryan Adams doesn’t have any good ones, so check out Moroccan Role and Follow The Lights, and make an extra point to keep an eye out for his Pax-Am releases, which seem to be coming about once every month lately. (Jacksonville, Vampires, and Do You Laugh When You Lie?, each released in fall 2014, feature great songs that Ryan seems to like churning out whenever he has a couple of days downtime).
• Official releases only. This one’s a little difficult, because the line between “official” and “unofficial” in Ryan Adams’s world is a little blurry. And many would argue that some of Ryan’s best work came on albums that were only released as internet bootlegs. That said, many of those unofficial albums are largely made of up of songs that later appeared on official releases, so to include them would be to build too much redundancy into this effort. For a great primer on Ryan Adams’s extensive unreleased catalog, check out Steven Hyden’s recent piece on Grantland.
• Whiskeytown albums count. They’re as much a part of the proper Ryan Adams experience as his solo stuff, and were huge in shaping his sound.

So without further ado, here we go:

18. Ryan Adams & The Cardinals, III/IV (2010)

A two-disc set of leftovers from the 2006 sessions that created Easy Tiger, it’s easy to see why this one went unreleased for so long: there’s not a single memorable track on it. I’ve only listened to this album twice, and both times, I regretted it. Feel free to skip it entirely.

17. Ryan Adams, Orion (2010)

As the beginning of this list makes clear, 2010 was sort of a down period for Ryan Adams. This collection, which Adams called a “sci-fi metal opera,” wasn’t entirely meant to be serious, which is why it ranks a hair ahead of III/IV. For serious fans only.

16. Ryan Adams, 1984 (2014)

Ten tracks clocking in at a total of twelve minutes and forty-two seconds—yes, you read that correctly—1984 was a package of quick and dirty punk-oriented tracks inspired by Husker Du. Its length renders it mostly a curiosity piece. The thing is, there are some damn good songs here—or at least there could have been, had they been given the time to unfold completely.

15. Ryan Adams, Rock N Roll (2003)

Thrown together in a couple of weeks as a sort of “fuck you” to the record label for rejecting the far superior Love Is Hell, many Ryan Adams fans consider this to be one of his strong ones. Despite a few standout songs, I respectfully disagree. “So Alive,” a little reminiscent of U2’s early glory days, is one of the best rock songs Adams has done. “Shallow,” which channels Oasis, and the back-to-back, loud-to-soft juxtaposition of “Note To Self: Don’t Die” and “Rock N Roll” are also highlights. That said, the rest of the album feels half thought out—which of course it was.

14. Ryan Adams & The Cardinals, Cardinology (2008)

There are some fantastic rock singles here: “Fix It,” “Magick,” “Cobwebs,” and “Crossed Out Name” come to mind. But nothing feels cohesive about this album. It’s a collection of rock songs just slapped together, and Ryan himself doesn’t seem to be having any fun anymore. After this one, he took a self-imposed hiatus for the next three years. The holiday served him well, sparking his current renaissance.

13. Whiskeytown, Faithless Street (1995)

I almost hate putting this one so low, because its high points are damn high. Adams was only 21 on this, his first major release, and it shows—in a good way. Blending rock and country in that signature way we’d soon be calling “alt-country,” the songs on Faithless Street are gritty and high-energy. “Midway Park” is the perfect starter, and maybe the quintessential track if you want to understand Ryan’s sound during this era. “Too Drunk To Dream” is a perfect little country song, even as the lyrics strain the line between homage and parody. And “Desperate Ain’t Lonely” was the first showcase of what would prove to be Ryan’s greatest strength: his ability to write a quietly devastating ballad. So why does this one rank relatively low? There’s a lot of filler outside the handful of standout tracks. Adams was still learning how to put together a coherent album. That would come soon.

12. Ryan Adams, Easy Tiger (2007)

This one falls prey to the same flaw that held back Cardinology: it sounds more like a B-sides collection than an actual album. But the songs, standing individually, are a hell of a lot better, and you can’t afford to miss “Two” (his duet with Sheryl Crow, and one of the best singles he’s ever recorded), “These Girls,” or “Oh My God, Whatever, Etc.”

11. Whiskeytown, Strangers Almanac (1997)

Whiskeytown’s second release softened the band’s edges (some would say to its loss) but also found a more professional, more coherent sound. It was Adams’s first success in crafting a unified album, and that would pay dividends later in his career. This one also gave the band its first real hit, “16 Days,” which sounds a little conventionally Nashville, but is held up by an unforgettable melody. My personal favorite track, “Turn Around,” comes from Ryan’s rock side and sounds like a bit of an anomaly on this mostly country-fied album, but previews a lot of his music to come.

10. Whiskeytown, Pneumonia (2001)

Recorded in 1999 but released by the label only after the band had broken up and Ryan had gone solo, Pneumonia is an intriguing view into an alternate history. Not as coherent as Strangers Almanac, this album nevertheless has the most mature songwriting that Whiskeytown produced, and is chronologically the first of Ryan Adams’s albums to sound like what we now know as Ryan Adams. “Jacksonville Skyline” and “My Hometown” show a songwriter now grown-up enough to look back at his youth with both regret and affection. “Reasons To Lie” and “Under Your Breath” are stunning ballads, helped along not just by Ryan’s songwriting but by the musical chemistry of a band of near-equals (something he’d never quite experience again). “Crazy About You,” the album’s most well-remembered single, isn’t quite country and isn’t just rock—it’s a seamless hybrid of the two. And you might just recognize the Big Muff sound of vintage Smashing Pumpkins in the instrumental break of rocker “Sit & Listen To The Rain”; that’s because James Iha stops by for a visit. Easily the most accessible of Whiskeytown’s releases, this one makes you wonder what might have been, even as it still takes a backseat to the music Ryan Adams would put out as a solo artist shortly thereafter.

9. Ryan Adams, 29 (2005)

Released at the tail end of a 2005 that saw Adams release three albums, 29 feels like a brief musical exhale after an explosion of creativity. Full of piano ballads, with only a few rocking moments in-between, it’s a beautiful album with hushed moments like “Nightbirds” or “Elizabeth, You Were Born To Play That Part” (an ode to the many actresses he’s dated?) or, best of all, the jaw-dropping “Voices,” which closes the album with the best five minutes of vocal work Ryan Adams has ever recorded. If this album trails behind his other 2005 releases, it’s not by much, and it’s only because it feels a little less well-themed: as if he needed a vehicle to release the songs that didn’t quite fit in anywhere else.

8. Ryan Adams & The Cardinals, Jacksonville City Nights (2005)

Released a few months before 29, this is easily the most country album Adams has done. Like a Waylon Jennings throwback, song after song on Jacksonville City Nights sounds like distilled Appalachia. “Dear John,” an aching duet with Norah Jones, is one of the best songs she’s ever had the good fortune to be associated with. “The Hardest Part” is vintage Adams, while “A Kiss Before I Go” and “Hard Way To Fall” are barn-raising mementos to the days when the genre was still referred to as “country & western.” Maybe not the most representative album in the Ryan Adams collection, but definitely one of the best.

7. Ryan Adams, Demolition (2002)

A B-sides album collecting the best tracks from three unreleased solo albums—The Suicide Handbook, The Pinkhearts Sessions, and 48 Hours—2002’s Demolition comes off sounding more than a little schizophrenic. New wave punk stands alongside country ballad here, which means it has absolutely none of the artistic maturity of 29 or Jacksonville City Nights. But if you’re looking to hear all the various facets of the Ryan Adams sound in one place, this isn’t a bad place to start. And goddamn are the songs here good: if you tried to make a top-ten list of his best ballads, “Desire,” “Cry On Demand,” “She Wants To Play Hearts,” and “Tomorrow” would all have to be in the conversation. And you can’t overlook the more upbeat moments here either, like the breezy country number, “Chin Up, Cheer Up,” the soaring “Hallelujah” (not to be confused with the endlessly-covered Leonard Cohen song), or the appropriately-named rocker, “Nuclear.” This may not be a proper album, per se, but the songs make it essential listening for the Ryan Adams rookie.

6. Ryan Adams, Ryan Adams (2014)

Last year’s self-titled homage to Ryan Adams’s near-namesake, Bryan Adams (seriously, compare the album covers), this is an 80s-drenched love letter to rock-and-roll that easily outshines Rock N Roll. The songs are just plain better, starting with “Gimme Something Good” and the lone ballad, “My Wrecking Ball,” and continuing all the way through the driving angst of “I Just Might.” It’s also a lean album, with not a minute of fluff, embracing the newfound minimalism that seems to have reinvigorated Adams’s career. Whether the new sound is the start of a longer-term trend or just another in a lifelong set of unexpected turns remains to be seen. But I’m excited by the possibilities either way.

5. Ryan Adams, Ashes & Fire (2011)

The beginning of his recent critical revival, Ashes & Fire was seen as a return to Ryan’s beginnings. Whereas the four albums that preceded it had felt increasingly labored (and even, in a different way, the three theme albums that had preceded those), this one feels completely effortless. It’s lazy Sunday morning roots rock, flavored with folk and seasoned with the happiness of a new marriage to Mandy Moore and the life experience of a man learning to love music again after a long hiatus (forced by the onset of Meniere’s disease). “Lucky Now” ranks among his best singles, while “I Love You But I Don’t Know What To Say” is soul music at its best. A perfect album from start to finish.

4. Ryan Adams & The Cardinals, Cold Roses (2005)

It takes balls to release three albums in one year; it takes bigger balls for the first of them to be a double album. Of all the Ryan Adams entries on this list, Cold Roses sounds the most purposeful. Marrying country and psychedelic rock isn’t as easy as it sounds, and it’s clear that a lot of thought went into making this collection work. What’s remarkable is how diverse and yet cohesive it sounds at the same time. “Magnolia Mountain” is the Greatful Dead mixed with moonshine; it sounds like nothing else in the Ryan Adams catalog, and that’s why it’s so special. “Cherry Lane” and “Beautiful Sorta” manage to sound both pretty and dirty. There’s also sappy piano stuff (“How Do You Keep Love Alive”), trucker rock (“Let It Ride”), and a lot of crooning (“Sweet Illusion”). Somehow it all makes sense together. But my favorite moment is how the bottom drops out for “Meadowlake Street” then builds, slowly, slowly, up from a whisper to a crash. This album never should have worked. It totally did.

3. Ryan Adams, Gold (2001)

This is the one that got me listening to Ryan Adams. Ironically, the song that brought it to my attention, “New York, New York,” is one that Adams has all but disowned. It’s a great little pop song, but one that is overshadowed once you hear everything that follows it. “La Cienga Just Smiled,” “When The Stars Go Blue,” and “Harder Now That It’s Over” are the three best ballads he’s ever recorded—period. “Nobody Girl” and “Enemy Fire” rock out. “Wildflower” is strangely sweet and lighthearted for an Adams song. “Firecracker,” “Answering Bell,” and “The Rescue Blues” meet somewhere in the middle, fusing rock and country so effortlessly that they seem like their own genre. Gold is the natural evolution of everything Ryan Adams has done. Some say it’s too polished, but polish is never something from which he’s shied. It’s pure songwriting brilliance, and it falls to number three only because Adams amazingly managed to outdo this not once, but twice, in his career.

2. Ryan Adams, Heartbreaker (2000)

I know it’s blasphemy to put this at #2, but bear with me. His first solo release, Heartbreaker is considered by most to be the quintessential Ryan Adams album. It sounds less glossy and more authentic than anything else he’s ever done. It features his all-time best song (and one of the best tell-off songs in country music), the iconic “Come Pick Me Up.” And it has a lot of other ridiculously good tracks, including the mainstay ballad “Oh My Sweet Carolina” (recorded here with Emmylou Harris and endlessly covered ever since), the rocking and rollicking “To Be Young (Is To Be Sad, Is To Be High),” the dark and moody “Bartering Lines,” and the sugary ode, “Amy.” It’s heavy on Adams’s country influences, but it never sacrifices the rock edge that makes his music unique. Rebellious and ambitious, it’s an album fueled by young cockiness that just so happens to have the artistry to back it up. There’s no denying that if you’ve never heard a note of Ryan Adams, Heartbreaker is the place to start.

1. Ryan Adams, Love Is Hell (2003)

So if Heartbreaker is so great, why did I put Love Is Hell as my top choice? Because this is my damn list, and because everyone else goes with Heartbreaker. And because I honestly think Love Is Hell is the most underrated album in his catalog, and it has always been my own personal favorite. It’s darker than anything else he’s done—which is why the record label initially rejected it in favor of the more commercial Rock N Roll. But Ryan Adams’s sharpest moments have often happened when he embraces the sadness, and nearly everyone agrees that Love Is Hell was the superior piece of work. The guitar work here is shinier, full of echo and ambiance that recalls Brit rock or shoegaze more than country or folk. Case in point, the stark cover of Oasis’s “Wonderwall” actually improves on the original, while “Political Scientist” builds slowly into a soaring conclusion worthy of early Radiohead or Coldplay. “I See Monsters” is way prettier than it has a right to be, while “English Girls Approximately” brightens things up before closing on an ominous coda, the guitar bouncing off distant walls like it’s lost in a cave. This album is Ryan Adams at his most lost, but also his most confident. It’s a crossroads of sort, when he was tired of being the man he’d always been and willing to try anything to find out the man he wanted to be. It’s a more challenging listen, but also a more rewarding one.

The Song Mix: Ryan Adams 101

Picking just one song to represent each Ryan Adams album is an impossible task. I tried anyway. I didn’t aspire to pick the best song, or even my favorite song. The idea here was to pick the one song that most captured the sonic flavor of that album. In a career spanning every point on the spectrum between rock and country, these are your signposts. If you like a particular song, that’s your starting point; check out the rest of the album. You won’t be disappointed.

Download here: Ryan Adams 101

1. Midway Park (Faithless Street)
2. 16 Days (Strangers Almanac)
3. Jacksonville Skyline (Pneumona)
4. Come Pick Me Up (Heartbreaker)
5. When The Stars Go Blue (Gold)
6. Desire (Demolition)
7. Political Scientist (Love Is Hell)
8. So Alive (Rock N Roll)
9. Magnolia Mountain (Cold Roses)
10. A Kiss Before I Go (Jacksonville City Nights)
11. Nightbirds (29)
12. Two (Easy Tiger)
13. Fix It (Cardinology)
14. Lucky Now (Ashes & Fire)
15. Gimme Something Good (Ryan Adams)