When Bob Dylan performed “He Was a Friend of Mine” under the cryptic label “#019,” he wasn’t just honoring a lost soul—he was whispering a coded lament full of hidden grief, possible political commentary, and echoes of a friendship too complex to name; some believe this version holds clues to a private tragedy, others claim it was Dylan’s quiet rebellion against official narratives, but no one can agree on who “he” really was—or why Dylan chose this moment, this format, this number—what secrets are buried beneath this simple, aching ballad? click the link to read more.

There are songs that live quietly in the corners of Bob Dylan’s career—songs that never became hits, were rarely played live, and yet seem to carry more weight than entire albums. “He Was a Friend of Mine” is one of them. When Dylan recorded it in the early 1960s, it was already an old folk tune, passed from singer to singer, altered by voice, memory, and intention. But when Dylan sang it, especially in the obscure and cryptically labeled “#019” version, something shifted. It stopped being just a folk lament. It became something else—personal, political, and elusive.

The song, as Dylan performed it, was simple on the surface: a man mourning the death of a friend. The lyrics were sparse, the melody slow and haunting. “He was a friend of mine / Every time I think about him now / I just can’t keep from cryin’.” In Dylan’s voice, young and raw, the grief felt more than sung. But it’s not just the emotion that has kept listeners returning to this version—it’s the mystery surrounding who the “friend” actually was.

The “#019” designation appears in certain archival tracklists and bootlegs, especially among collectors who trace Dylan’s early recordings with near-biblical fervor. Some believe the number was used internally to catalog a set of studio takes from a particular session—likely in 1961 or 1962, during Dylan’s time in the Columbia studios with producer John Hammond. Others, however, have speculated that “#019” holds a deeper meaning: a reference to a person, an event, or even a hidden system of messages encoded in Dylan’s early work.

Over the years, speculation about the identity of the “friend” in the song has ranged widely. Some say it refers to a literal friend—Dave Van Ronk, for example, or another Greenwich Village folk singer who died young or vanished from the scene. Others suggest it was a metaphor for the death of innocence in America, a theme Dylan would explore more overtly in later songs like “The Lonesome Death of Hattie Carroll” and “Only a Pawn in Their Game.”

But one of the most persistent theories links Dylan’s version of “He Was a Friend of Mine” to the assassination of President John F. Kennedy. Although Dylan never officially released a Kennedy-specific version of the song, other folk artists—most notably The Byrds—reworked it into a JFK elegy. The tone of Dylan’s rendition aligns eerily well with that atmosphere of loss and national trauma. Could “#019” have been Dylan’s private nod to that grief, quietly encoded in a time before he felt ready—or willing—to speak out more directly?

Adding to the intrigue is the fact that Dylan rarely performed the song live. It appeared in early setlists, sometimes with slight lyrical variations, but quickly disappeared from his concert repertoire. Fans who cherish this version do so almost in secret. It’s not on greatest hits albums. It’s not a track he’s returned to or reinterpreted in public. It lives in shadows—shared in bootlegs, archived in numbered lists, whispered about in forums.

And then there’s the performance itself. Dylan doesn’t embellish or dramatize. He almost seems to be holding something back, delivering each line with restraint that borders on emotional shutdown. That’s not unusual for Dylan, especially in his early years. But here, it feels especially pointed. It’s as though he’s trying not to reveal too much—not just about the friend, but about himself. As if by keeping the “he” unnamed, Dylan was also protecting something private, sacred even.

Some theorists have gone further still, suggesting that the friend referenced might have been a civil rights worker, perhaps someone Dylan met during his brief involvement in early activism. Others suggest the friend might not have died at all—but rather, disappeared metaphorically: a friendship lost to fame, betrayal, or ideological difference. Dylan was known to burn bridges in his rise, often quietly and without explanation. Perhaps this song was his only goodbye.

Of course, Dylan has never commented directly on the meaning of this version. He rarely explains any of his songs, and when he does, the explanations only deepen the confusion. In a 1966 interview, when asked about older folk tunes he adapted, Dylan said, “Sometimes I sing ‘em for me. Not for anyone else.” That line, cryptic and cold on the surface, might be the key to “He Was a Friend of Mine.” Maybe it was never meant to be public. Maybe it slipped out.

The title “#019” itself remains a cipher. Was it just a studio reference? Was it Dylan’s own system of classification? Or was it a nod to something more significant—an address, a date, a code known only to him and a handful of others? Theories abound, but certainty remains elusive.

And yet, the ambiguity is part of the song’s power. In an era where every lyric is dissected, every artist’s intent demanded, there’s something almost radical about a song that refuses to explain itself. Dylan’s “He Was a Friend of Mine” doesn’t offer answers. It offers an ache. A memory. A shape without a face.

For many fans, that’s enough. The version labeled “#019” is not just a recording—it’s an artifact. A relic from a time when Dylan still walked between the street corners of New York and the dark corners of his own mythology. A reminder that not all grief needs to be named to be felt.

Whether the song was about a president, a partner, or simply the fading of youth, it endures. Quietly. Uneasily. Like many of Dylan’s most powerful songs, it doesn’t insist on being heard—but once it is, it never leaves.