Generation Mixtape

For the majority of his career, Gregrory Alan Isakov has quietly flown below the proverbial radar, all the while dutifully assembling a catalog of timeless classics. For anyone reading this, I’m likely preaching to the fully converted, but I’ll offer the following background as a blanket ‘just-in-case.’

Born in Johannesburg, South Africa, but raised in Philadelphia, Pennsylvania, Isakov eventually settled in Colorado and self-released his debut (Rust Colored Stones) back in 2003–Songs for October followed two years later. While his haunting vocals, poetic lyrics, and intricate guitar playing were in place from the beginning, his songwriting reached a whole new level on 2007’s That Sea, the Gambler, a release that expanded Isakov’s audience and earned him widespread accolades.

From that point forward, Isakov continued to write, record, and tour on a schedule that allowed him to balance his career with the seasonal demands of running a farm (that’s right, the man owns a farm). While it isn’t the only reason for my enduring fandom, Isakov’s DIY ethos and reliably independent streak sure resonates with my inner punk-rocker. Bottom line: Isakov is the real deal.

His catalog may feel a bit scarce, especially considering how long he’s been making records, but that’s largely due to Isakov’s process. Speaking to Joel Oliphint back in 2022, Isakov revealed the following: “There’s all this pressure on bands to put out a record every year, and I’ve never done that. It’s always been four or five years between records. And I’m not hanging out. I’m working pretty hard on them in those four or five years.”

Now, per usual. before we dive into my ranking, there are a few caveats I’d like to mention:

*Caveat Number One: While I typically restrict my lists to full-length studio releases, given the relative brevity of his catalog, I’m also going to be reviewing Isakov’s live (and very essential) album with the Colorado Symphony Orchestra. 

*Caveat Number Two: I will not, however, be reviewing his self-released debut (Rust Colored Stones) for no other reason than it’s not currently available on any streaming platforms and is otherwise hella out of print. 

**Caveat Number Three: It should go without saying, but I’m going to say it regardless: I’m a massive fan of virtually everything Isakov has released. Any and all criticisms are subjective and should be taken with a grain of salt.

***Caveat Number Four: I’d like to file anything that I’ve written below in the ever-so-subjective ‘prisoner of the moment’ category. If I were to repeat this process six months (or minutes?) from now, my results would probably change.

6. Songs for October (2003)

Featuring a pair of tracks (“Black & Blue,” “Salt and the Sea”) that ultimately reappear on That Sea, the Gambler, one might assume that Isakov’s debut (at least, according to streaming services) E.P. is the work of an artist searching for a sound. And in some ways, it is. Still, the record’s sparse, lo-fi production also shines a spotlight on Isakov’s singing and fingerpicking prowess, something that the studio polish of future-releases tends to obscure. Add to that a couple of must-listen gems ( “Shining Offa You” and “Crooked Muse”), and you have yourself a captivating glimpse into Isakov’s musical roots. While it ultimately lands at the bottom of this list (primarily due to the short run-time), Songs for October is an oft-overlooked release that’s absolutely worth revisiting.

Living Proof (Highlights):

While the list of top-shelf Isakov ballads is a mile long, the first entry on that list would probably be “August Clown.” The bare-bones production is an asset here, as the ‘live’ feel highlights the emotion-drenched nuance in Isakov’s performance.

Dark, Dark, Dark (Lowlights):

There’s nothing wrong with the versions of “Black & Blue” and “Salt and the Sea” that appear on Songs for October, but the revised versions ultimately render the initial attempts a bit, well, redundant.

Words Mean More at Night (Favorite Lyric and/or Moment):

I’m goin’ back where I belong, where the time is right and straight and slow – “August Clown”

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5. Evening Machines (2018)

Released in 2018, Evening Machines finds Isakov pairing his signature acoustic-driven Americana sound with some amped-up indie rock. Perhaps the most lush, layered album in his catalog, Evening Machines also finds Isakov pushing sonic boundaries in all directions. For instance, “Berth” continues Isakov’s tradition of heart-wrenching album-openers, but the track’s atmospheric, organ-heavy instrumentation adds an overtly cinematic touch to one of Isakov’s best lyrics to date.

Unfortunately, the expansive mix also results in a handful of tracks that sound a bit, dare I say, overproduced? Undoubtedly informed by his experience performing with the Colorado Symphony, the orchestration on “Was I Just Another One” tends to overpower Isakov’s otherwise tender performance, and the reverb-drenched “Caves” has always felt like a solid, upbeat song sorely in need of a remix. Still, Evening Machines sports a handful of instant-classics (“San Luis,” “Southern Star”) and is one of Isakov’s most consistent albums in terms of mood. The record’s placement on this ranking is less an indictment and more a testament to the incredibly high consistency of Isakov’s work.

Living Proof (Highlights):

Sounding like something that might have featured in a Leone western, “Where You Gonna Go” is a late-album gem that finds Iskaov bathing his potent lyrical imagery with a heavy dose of ambient atmosphere.

Dark, Dark, Dark (Lowlights):

The four-song run of “Caves,” “Chemicals,” Dark, Dark, Dark,” and “Too Far Away” represents the only prolonged stretch of any Isakov album where I feel the songwriting fails to impress. That’s not to say that the songs are bad, because they each have a certain charm, but together, they essentially mute the momentum established on the front half of Evening Machines.

Words Mean More at Night (Favorite Lyric and/or Moment):

did i stumble through your darkness, or was i just another one – “Was I Just Another One”

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4. Gregory Alan Isakov with the Colorado Symphony (2016)

Iskaov’s 2016 ‘live’ album is anything but your run-of-the-mill tour document. While a traditional ‘off-the-board’ bootleg would have more than sufficed (especially given the consistency of the man’s live performances), Isakov opted to toss convention to the wind, and instead, shared the stage with the Colorado Symphony. The album opens with a cover of Ron Scott’s “Liars.” This lone new addition to Isakov’s catalog is easily worth the price of admission alone. From there, the eleven song set features a potent mix of fan favorites and deep cuts and finds Isakov and his band in fine form.

And then, of course, there’s the whole ‘orchestra’ thing, which provides embellishments that elevate a handful of these tracks to ‘definitive version’ status. To take nothing away from their studio counterparts, songs like “Dandelion Wine,” “Master & a Hound,” and “That Sea, the Gambler” are cast in new and revelatory hues. The results are incredibly affecting, so much so that the only real gripe here is the abbreviated runtime (presumably due to the inherent time-restrictions of vinyl).

Living Proof (Highlights):

In addition to the breathtaking “Liars,” the orchestral treatment of “If I’m Go, I’m Goin” somehow takes an already flawless song to a whole new level.

Dark, Dark, Dark (Lowlights):

While the penultimate placement of “Unwritable Girl” makes complete sense within the context of the That Sea, the Gambler, the track makes for an underwhelming close to this otherwise brilliant live set.

Words Mean More at Night (Favorite Lyric and/or Moment):

I sold all this land, to buy me some dreams
just like those movies we played when we were kids – “Liars”

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3. That Sea, the Gambler (2007)

That Sea, the Gambler is arguably Isakov’s most cohesive listen from cover to cover. While Songs for October served its purpose as a debut (of sorts), That Sea, the Gambler is, for all intents and purposes, Isakov’s introduction to the world. And, oh what an introduction it is. In fact, it’s difficult to overstate just how much Isakov grew as both a singer and writer between the aforementioned releases. Be it the stunning opening run of “All There Is,” “The Stable Song,” and “Black and Blue,” or the epic title track, each and every song functions like a chapter in a much larger story. 

Musically speaking, That Sea, the Gambler finds Isakov in ‘solo-acoustic mode’ for most of its running-time, something that lends an air of accessibility to the album. Tracks like “John Brown’s Body, “3 a.m.,” and the infectious, alt-country toe-tapper, “Raising Cain,” would easily fit on any coffee-shop playlist. Still, for all of its refined cohesion, there’s little here that truly challenges the singer-songwriter template. Of course, that’s part of the charm, but for all of its strengths (and there are many), That Sea, the Gambler still feels like a foundational work from a still-developing artist. Nonetheless, it’s an impressive foundation.

Living Proof (Highlights):

Isakov has long since perfected the haunting ballad, but “San Francisco” (featuring lyrics that read like pages from a lost Hemingway novel) is one of his first (and best).

Dark, Dark, Dark (Lowlights):

Ending an album on a somber note has long been Isakov’s tradition, but if I were ranking album closers, “That Moon Was Red & Dangerous” would probably be at the bottom of this list.

Words Mean More at Night (Favorite Lyric and/or Moment):

But if this is all in our minds, it’s all in our minds honey, would you mind getting out of mine – “All There Is”

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2. This Great Northern Hemisphere (2009)

We have now officially entered ‘toss-up’ territory, as I consider the next two releases masterpieces. In fact, my final order switched a number of times. And I was forced to resort to some rather petty nit-picking in order to decide which record would be the one to rule them all. With that in mind, it’s important to note that despite its placement on this list, 2009’s This Great Northern Hemisphere showcases some of Isakov’s finest songwriting. The record also finds the singer pushing against the well-established Americana boundaries for the first time.

Where the understated “Dandelion Wine” continues his streak of riveting album-openers, “Evelyn” and title-track find Isakov in full-on ‘rock’ mode, adding a whole new dimension to his sonic palette. Meanwhile, pensive numbers like “Big Black Car” and “Master & a Hound” showcase Isakov’s continued development as a lyricist. Speaking of ballads, “Words” is practically a songwriting masterclass, and his take on Leonard Cohen’s “One of Us Cannot Be Wrong” is simply brilliant (thanks in no small part to Brandi Carlile’s guest vocals which can be heard on half the album).

As for the aforementioned nit-picking, This Great Northern Hemisphere feels ‘slightly’ padded. At forty-eight minutes, the thirteen track affair is right up there with Isakov’s longest musical statements to date. While they certainly add to the vibe, “Virginia May” and “Fire Escape” are far from essential listening, and removing them from the album probably results in a leaner, meaner tracklisting. 

Living Proof (Highlights):

While I could almost pick any song at random and cite it as a highlight, “Master and a Hound” earns the spotlight here as a highwater mark for Isakov’s vocal abilities.

Dark, Dark, Dark (Lowlights):

It was already covered above, but “Fire Escape” would be the first (and probably the only) thing to go if I wanted to trim the runtime.

Words Mean More at Night (Favorite Lyric and/or Moment):

where were you when i was still kind – “Master & a Hound”

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1. The Weatherman (2013)

Arguably Isakov’s finest hour, 2013’s The Weatherman is a masterful album that showcases Isakov’s exceptional songwriting skills and unique musical style from cover to cover. The record opens with the hauntingly beautiful “Amsterdam,” a contender for Isakov’s strongest single that sets the tone for the rest of the album. From there, Isakov delivers one eventual live staple after another. Tracks like “Saint Valentine,” “Second Chances,” and “Sparks” are stage-ready anthems that help round out what might also be Isakov’s most accessible album.

Beyond the impressive opening salvo, The Weatherman finds Isakov settling into a more reflective posture. “The Universe,” “Honey, It’s Alright,” and “All Shades of Blue” are some of his most effective ballads, and “Suitcase Full of Sparks” is a welcome strumfest that helps shake up the album’s predominantly quiet back-half. And then, of course, there’s “She Always Takes it Black.” Not only is the track a brilliant coda, it represents yet another high-water mark for Isakov’s writing.

Speaking of lyrics, “The Weatherman” finds Isakov in a reflective mood, ruminating on life’s fleeting moments and the search for meaning and purpose. Isakov’s poetic lyrics are filled with vivid imagery and metaphors, which provide a sense of intimacy and vulnerability throughout the album. Add to that introspective themes paired with a timeless stripped-down sound, and you have a sense of intimacy that makes for an  immersive listening experience that rewards repeated listens.

Again, it was essentially a toss-up, but today, right now, my top choice is, well, umm…

Living Proof (Highlights):

“Honey, It’s Alright” and “O’ City Lights” are low-key gems that highlight Isakov’s masterful command of musical and lyrical subtlety.

Dark, Dark, Dark (Lowlights):

As with any album of this caliber, anything resembling a real ‘lowlight’ is difficult to find. That said, for all of its ambiance and charm, the brief instrumental “California Open Back” is a shining example of ‘filler.’

Words Mean More at Night (Favorite Lyric and/or Moment):

she always takes it black, but you’ll love her till it all goes dark, you’ll love her even after that “She Always Takes It Black”

One Final Note: Two things if you’re still reading: thank you, and I hope this article inspires a return visit to the Isakov catalog. I might have just made a case for ‘worst-to-first’ ranking, but, to be honest, the man’s work is pretty unassailable.