1.) John Prine - John Prine

No other album in my lifetime has been as important as this album. Furthermore, no other album has spoken to the cancerous qualities the American dream had had on its citizens. Who knew a 24 year old postman from Illinois could predict the cyclical rage of the working class seeing their sons die in pointless wars, succumb to addiction as a coping mechanism, their small town pride diminished by capitalist greed, or the elderly get left behind amidst a world that is moving too fast? There is no wasted breath on this record and time has rightfully placed him where he belongs: next to giants of the craft such as Bob Dylan, Hank Williams, and Kurt Vonnegut Jr.

2.) Gene Clark - No Other

This is an album that continues to fascinate me every time I put it on. A sober psychedelic experience filled with equal parts wisdom and poetry. The instrumentation is volcanic in its presentation with Gene’s voice and perspective chiseling its way into your soul. I’ve yet to hear a record that comes close to matching this record’s balance of country, gospel, and cosmic funk. It’s the direction that alt-country should have taken instead of the near-constant Gram Parsons clones of the last 50 or so years.

3.) Neil Young - After The Gold Run

After The Gold Rush is Neil young free from expectations. If Harvest is him at his most Laurel Canyon folk-country and Everybody Know This is Nowhere is him writing the Crazy Horse handbook, this record is Neil at his most skeletal and personal. He would become more cynical—listen to On The Beach—but no other album gives you a picture of Shakey at his most bright eyed and threadbare.

4.) Lucinda Williams - Carwheels On A Gravel Road

A monumental statement for a peerless artist. Cyclical family trauma. Survivor’s remorse. Complicated love. Lucinda tackles subjects other artists wouldn’t dare touch with the lyrical economy of a Farside cartoon. I don’t think I’ve ever heard a song tackle the shared disappointment of a relationship falling apart like these lines from “Metal Firecracker”:

All I Ask

Is don’t tell anybody the secrets

I told you

5.) Bob Dylan - Street-Legal

I went with Dylan in my fifth spot because it was a mountain I was too scared to reckon with. While my younger self would say Highway ‘61 (my ideal sound of any band on record) or Blonde On Blonde, Street Legal is the Dylan record that is connecting with me the most at my current age. This is a Dylan who has seen some things. This is a Dylan who has BEEN through some things. Unlike Blood on the Tracks, he can no longer use the pain as an influence, he has to work through it. For my money, songs like “Changing Of The Guards” and “True Love Tends To Forget” stand with anything he has ever written. You can’t really judge Dylan on this kind of metric. Your life adapts to his prose and reverse and forward and reverse yadda yadda. The bard of verse-chorus can’t be denied.