“I didn’t know you were a Deadhead,” my coworker said one day after she’d heard me whistling “Sugar Magnolia.” I cringed. Her words hinted at a conspiratorial discovery—I was one of her! Of them! All along! The chasm of Grateful Dead lore with its tie-dyed everything and dancing bears began unfolding from my cubicle into oblivion, threatening to subsume me.

“Oh, God no,” I said, and explained that though I do like many—a lot, even—of their songs, I wasn’t a Deadhead, or any other sort of head, and didn’t like to identify myself through tangential affiliations. This of course was just a bullshitty sentiment of my cynicism, but when faced with a monolithic entity like the Grateful Dead it does feel dishonest of me to claim any half-hearted allegiance.

There were definitely times when I wanted to be a Deadhead. My best friend and music partner was raised up in the Dead by his father, who had toured with them in a Volkswagen pickup truck in the ‘70s and would still pick up his old Martin to play their songs with us. China cat sunflowers nurtured by boxes of rain and sunshine daydreams—the Dead’s music was a second language to them, spoken without effort or affectation. I never knew the words or melodies well enough to sing along and could barely track the chord changes as I flubbed along on my bass, but I could feel how music was an inextricable part of their family, a sensibility that was both close to me and out of each.

Later on, the Dead were the gateway wave my friends rode in to other jam bands. Suddenly they were all Deadheads, imitating their cooler, older brothers who themselves had become Deadheads as a means of communicating their counter-culture status. They had long hair. They wore tie-dye. In the thick of it, they started trading recordings of live concerts, the “tape exchange,” via an online forum. The canon of recordings dated back to nearly the beginning and had been fostered by the Dead themselves, who had encouraged their fans to record. This was still well before Napster, et al, so trading the Dead involved overstuffed binders of burned CDs and lots of parent-paid postage. I listened to some of the concerts, listened to my friends tell me about the merits of the concerts, but it never hooked me.

What was the point of listening to a hundred versions of the same songs played at concerts three decades prior? How much listening, how much sifting through and comparing would one have to do to find the rendition that most spoke to them? That singular performance that would elevate and transport the listener beyond corporeal bounds? Perhaps even to a grateful death? (Too easy, I know.) I had the Greatest Hits and it did me good. The cost-benefit ratio only confirmed the great endeavor required to become an honest-to-god Deadhead. You were either born into it or devoted your whole life to becoming it—and yet, when caught whistling a single song, some folks would lump you in all the same.

But of course you don’t have to be a Deadhead to enjoy the Grateful Dead, and Workingman’s Dead is a good, important album. Good because with only eight tracks at just over thirty minutes, WD accomplishes a lot. Bookended by two of the Dead’s most popular songs, “Uncle John’s Band” and “Casey Jones” (the latter kicking into gear on that infamous illicit sniff), the album delves into a nitty gritty folklore of those hardscrabble laborers that built up America only to be broken by it. Miners, road and rail workers, lonely souls getting love while they can, only to beg for death at the end, be it delivered by dire wolves or dire weather. Good because the Dead can carry songs of kumbaya, lover’s lament, and jangly foot tappers without breaking stride.

Important because WD represents an intentional transition in the Dead’s style that would dictate their future successes. With WD, the Dead had to move beyond a band that could play good music, and become a band that could craft good songs, too. Less acid rock, more Americana. They brought the lyricist Robert Hunter on board and, after hanging around Crosby, Stills and Nash, developed their own folksy song-style with a focus on acoustic instrumentation and vocal harmonies, straightforward lyrics that told their tale and maintained the Dead’s particular weirdness. Those first big open-G strums of “Uncle John’s Band” were practically a thesis.

Important also because it seems one of the primary motivations for these changes was financial. Owing money from the extensive studio time of their previous album, coming off of a heavily publicized drug bust (later documented in the song “Truckin”), and having been essentially robbed by their manager, the Dead were in dire straits. They needed to make marketable songs and make them fast. Thus, the “workingman” of the title not only describes the thematic content of the song lyrics, but also the Dead’s experience writing and recording: here they were working through the challenge of stylistic change, making song-songs; here, also, they were working for that money-money. As the speaker of “Cumberland Blues” says, “Make good money, five dollars a day / Made any more, I might move away.” The work paid off—not only was WD a great success (even topping CSNY’s Déjà Vu in a Rolling Stone poll), but the songwriting and instrumentation practiced in WD laid the groundwork for their next album, American Beauty, which came out only six months later and is generally acknowledged as their best.

In part because of the proliferation of Grateful Dead recordings, both studio and live, in part because of how stand-out songs get separated from their genesis over time, I’d heard all of the songs from WD—again, liked them—but would not have been to reference the track list, or identify which rendition of the song it was I was hearing. Whether it was the studio version from 1970, a short, clean live version from Red Rocks from ‘78, or the remastered reissue in 90-what-have-you. But the songs by themselves are powerful alone, even with the ability to elevate and transport.

A few New Year’s Eves ago, back in my hometown in Kentucky, I gathered with my friend, his Deadhead father, and their family to celebrate. We were high-time drunk on rakia, a clear moonshine-like liquor that I’d brought back from Bulgaria, and starting to get boisterous. Unbeknownst to me, something turned in my friend’s mood. His dog jumped up to the table and knocked over a glass, and while we all scrambled to clean the mess I could hear him cursing at his fiancé, blaming and belittling her in a low, dark tone. She excused herself. His mother, who had heard his comments, was next to leave. Shortly thereafter, another conversation, another offense, this time to his sister, her subsequent exit. I was both upset by his actions, and worried for whatever might have caused him to act that way. To this day, I don’t know, and when we’ve spoken about it, he doesn’t remember. Either way, as the night came to an end, his father pulled out that old Martin, handed it to me, and asked for a song. It had been too long since I played, too long since I had sang with any confidence. I plucked out the first few notes of “St. Stephen,” but quickly faltered. Their disappointment was palpable. I handed the guitar back and my friend’s father made a toast to the new year. My friend lifted his glass but hardly moved his mouth in response. But when his father struck those first big open Gs of “Uncle John’s Band,” I could see my friend’s shoulders go loose as he started crying. Whatever it was inside him that was tearing him up, here in this music, a language of peace and love.

—Colin Lee