By Zach Jennings

Let’s set the ground rules first, as these types of lists can unleash the rage-hound in hard-core fans if not presented with a basic guide – or if those fans are general know-it-all assholes (but not you, dear reader, oh no not you). If the song is well known by casual Ryan Adams fans, we’re going to skip it here. Anyone who has been to a Ryan Adams concert can attest to hearing drunk, stoned or just really spirited fans screaming at him to play “Come Pick Me Up,” “When the Stars Go Blue” or “Winding Wheel.” Or, as Adams himself jokes during the crowd-talk portion after “Amy” on the recent Live From Carnegie Hall release, fans yelling “Wonder Wheel” or “Winding Wall” as they combine “Winding Wheel” and “Wonderwall” in the real life version of the “know when to say when” campaign.

Also, no covers here; they deserve and will ultimately receive their own list. And all of these songs are on actual, official studio albums that HAVE been released, so you won’t find anything from the Sad Dracula recordings or the sublime-but-unreleased 48 Hours on here. Again, those recordings have their own home, and we’ll deal with them accordingly in this space in the future.

Finally, I’m not touching Cardinology and on so I’m stopping at 2007’s Easy Tiger. I could write an entire thesis about how under-appreciated III/IV is (oh, I did that already, here), and as for everything Adams has done since then, well, I think it all needs to marinate for a few years more before being properly picked through.

Lastly, please note that I’ve decided to keep these in chronological order by release year to simplify things and to prevent arguments about the actual placement of songs. This is a personal list and, like most of you, my tastes can change depending on the moon or how much wine I’ve had. But for now, we’re off …

1) “Amy” (Heartbreaker)
This one isn’t much of a reach but we’ll start here because who doesn’t like an easy layup. From a production standpoint, this almost sounds like an Elliott Smith track with the slightly reverbed vocals. Just a perfect song of regret over a love lost and a track that really sets the thematic tone for the seminal Heartbreaker, despite it being the one track with a Beatles’ style string section on the record. One may argue that “Come Pick Me Up” is the centerpiece of Heartbreaker, but well, one would be wrong. “Amy” is and always has been the defining track that makes the rest of Heartbreaker work so well.

2) “Call Me On Your Way Back Home(Heartbreaker)
What starts off as another fairly haunted song about a love-torn soul seeking redemption provides us with one of the most unexpectedly poignant verses on Heartbreaker: “Oh baby, why did I treat you like I did/Honey I was just a kid/Bubblegum on my shoe/But you love me and I love you.”
By the time Adams reaches the bridge/outro and its “I just wanna die without you” refrain, he sounds resolute and almost at peace with the situation. No more pleading for a call that will never come; just the absolute recognition of a mistake that can’t be walked back.

3) “Harder Now That It’s Over (Gold)
While it was tempting to go with “Wildflowers,” “Harder Now That It’s Over” has lasted with me the longest off the much-maligned Gold.  The ’70s-style rock didn’t sit well with fans of Whiskeytown and Heartbreaker at the time, but there’s a sense of emotional rebooting here that resonates with anyone who can safely feel a shared sense of freedom after a toxic relationship has ended. “It’s harder now that it’s over/now that the cuffs are off” leads to the relief of being able to reassure the other that “You’re free, free with the history.” P.S. Also worth noting – this song and the majority of this album is EASY to play on guitar, even for the helpless among us, so bonus points for that.

4) “She Wants to Play Hearts(Demolition)
Also appearing on the unreleased Suicide Handbook, this song is a highlight on an otherwise spotty Demolition album of castaways and leftovers. Typical Adams with a brilliant lyrical verse, a crawling pace, a nice double entendre for “game of hearts” and a beautifully melancholic bridge that just drives the nails in deeper. This choice verse starts things off and it doesn’t get any happier: “I’m a broken toy/for a lonely girl/Use once and destroy/and go find some more.”

5) “So Alive” (Rock N’ Roll)

Not owing as much to The Smiths as to Morrissey with a heavy dash of the Strokes thrown in for good measure (and perhaps as a flipped middle finger to Lost Highway for refusing to put out Love Is Hell for, well, a lack of “hits”), “So Alive” is a straight-up rocker amongst an album of pretty blatant no-frills bangers. Sidenote: This self-destructive period also led to moments like this  infamous (but still wonderful) answering machine message Adams left for Chicago rock critic Jim DeRogatis:

6) “The Shadowlands” (Love is Hell)
Love is Hell has developed a bit of a cult following for the sheer moodiness of the tracks. As impossible as it is to find a proper album review without mention of the influence of the Smiths on Love is Hell, this would seem to be Adams’ own “Asleep” – just a gorgeous, moody piece of isolationist detachment. One could easily make this case for the album as a whole.  I fell asleep to this song on repeat for six weeks straight at one point, and as a bit of an insomniac to some degree, I mean that in the best, most comforting way possible.

7) “English Girls, Approximately” (Love is Hell)
Egads, it’s almost a light-hearted moment on Love is Hell! Put the handful of valium and tumbler of cheap whiskey down and step over to the window, Ryan. It’s sunny outside! Let’s take a stroll, shall we? This jangly track is about onetime Adams muse and British songstress Beth Orton and alludes to her frequently and obviously (calling her “Daybreaker,” Bethany, and Elizabeth – but stopping just short of calling her “Beth Orton” so as to keep the suspense alive). The whole thing seems to be just peachy until the song, closing down, reaches the should-be-obvious “Just three words, my love …” line. Instead of the “I Love You” (either explicitly said or just implied) that seemed a virtual lock, both tone and pace change suddenly as Adams, after a noticeable pause, instead wails, “You meant everything … you meant everything” repeatedly over a now unstable wall of sound replacing jangle with purposeful, Johnny Marr style electric guitar effects howling in defiance. The mood has now shifted from a very proper “fancy that” to a no-holds-barred “fuck this.”  Such is the unexpected drama of “English Girls, Approximately”.

8) “Now That You’re Gone” (Cold Roses)
Even novice Ryan Adams fans are probably aware that Cold Roses is an homage of sorts to the Grateful Dead. But while tracks like “Magnolia Mountain” and “Easy Plateau” are easy gets for the jam-band crowd, it’s the hidden gems on Cold Roses that really make it stand out. The lineup here is as good as it gets for Adams (just look it up and spare me 100 words, please). I was so taken with the Dead vibe of this album that I initially paid little attention to “Now That You’re Gone.”  It’s an oversight I’ll pay for in the afterlife if God happens to be a fan of the understated, but for now, I’m happy to be a late adopter. It lacks the bombast and the “bro-fist-pump” of the Dead-tinged tracks, but it’s quite possibly the best-written song on Cold Roses.  After reaching the chorus of “Now that you’re gone,” the add-on line, “… for good” almost gets lost in the shuffle. It’s a subtle addition, on purpose, and it adds additional weight to an already heady song.

9)  “If I Am a Stranger” (Cold Roses)
I won’t mince words here. This song is a standout on Cold Roses, but the glacially-paced unplugged version from Live at Carnegie Hall (and also from the Follow the Lights EP) pushes it into new classic territory. That version seems more like a Heartbreaker track than a Cold Roses cut, but damn if Adams doesn’t still deliver on this original. While diverging from the noodling Grateful Dead paint-by-numbers layout of a few Cold Roses tracks, this still has the country-oriented Jerry Garcia influence laid out to perfection. But again, contrast this with the unplugged version for two very different experiences; each of them great.

10) “September” (Jacksonville City Nights)
Even I have fallen victim to Jacksonville City Nights‘ ability to make me double-take what a good album it is. It’s about as cohesive an album as Ryan Adams fans could hope for, but it gets overlooked for schlock later in Adams’ catalog. So what’s so special about “September”? It’s actually tough to say, as it’s certainly not the most well-paced track. It’s just a little slice of subdued beauty on an otherwise bold and outwardly “country” album.

 11) “Hard Way to Fall” (Jacksonville City Nights)
Dammit, I may have to double up on this one … Not only is “Hard Way to Fall” one of the best pure country songs of the past 10-15 years, it’s one of the best songs from that era, regardless of genre. This is simply the mark of an artist at the peak of his songwriting prowess and a band that is incapable of doing anything other than hitting homeruns. This is 1998 Mark McGwire type domination. It’s amazing that this song never gained traction with the country music crowd in 2005, but it’s stood out as a fan favorite over the years.

12) “Strawberry Wine” (29)
Running at nearly 8 minutes of meandering faux-Marty Robbins storytelling, it would be easy to throw this one in the “don’t open until 2050” time capsule if it weren’t executed so perfectly.  I’d argue that the track that follows (“Night Birds”) was sonically superior and I’d be right, but that one doesn’t really make sense, lyrically — it’s a nice piece of reverb but it’s not the songwriting equivalent of a David Foster Wallace story written in Sanskrit, as “Strawberry Wine” is. What the hell is going on, here? I honestly wish I cared, but I just dig the Neil Young vocals and over-simplified arrangement too much to care. And the idea of Strawberry Wine (not Boone’s Farm) just takes it over the top as my “guilty pleasure in the Ryan Adams catalog.”  Again, if meandering, 8-minute tracks aren’t your thing, check out “Night Birds,” and wait for the “Into the Ooooooceeeaaannn” reverb! (I used to play “Night Birds” at full blast in my car because of that reverb. Then I tried to figure out what the hell the song was about and slipped into a weird psychosis for a week or so.)

13) “Carolina Rain” (29)
Ironically, but not in the Alanis Morissette sense, the best Grateful Dead tribute from Cold Roses may have actually surfaced on the very much maligned and well, actually kinda universally hated 29. I don’t get it either, but Adams’ voice here is as assured as Garcia’s and, while lacking any allusions to Magnolia Mountain or the Easy Plateau or other curious landforms of note, “Carolina Rain” pushes a slow but steady crime tail that gradually gets as disturbing as a McCarthy novel. What happened to the “two pretty girls” that were “seven and three”??? Why did you lay them down so they could see your house???  Was the Judge involved in any way???  Cormac, call me (but use a burner phone, for both our safety.)

14) “These Girls” (Easy Tiger)
There’s nothing particularly challenging about this track (or really any song on the aptly titled Easy Tiger, really); it packs about as much mystique as a soundtrack song, like “Lucky Now,” from This is 40. There’s no secret sauce here, just a good, radio-friendly (even though it was never a radio hit) song on an album that was filled with a lot of mediocrity (for Adams). And “These girls are better off in my head” is a line that many a man has made a credo for good reason.