Kris Kristofferson – “The Pilgrim, Chapter 33”: A Tale of Triumph and Turmoil
About the Song
Kris Kristofferson’s “The Pilgrim, Chapter 33” showcases the songwriter’s profound ability to craft characters with emotional depth and complexity. Kristofferson once revealed that the Pilgrim represented a mix of individuals he admired—particularly serious songwriters—while also serving as a reflection of himself. As he told CMT in 2007, “Most of them were people serious about songwriting, but an awful lot of us just looked like we were out of work.”
The song opens with vivid imagery: “See him wasted on the sidewalk in his jacket and his jeans/ Wearin’ yesterday’s misfortunes like a smile.” These lines immediately set the tone, painting the Pilgrim as a man who carries the weight of his choices with an unshakable resilience. The story unfolds to reveal a character scarred by hardship, driven by the pursuit of an elusive ideal, and haunted by the love and stability lost along the way.
Kristofferson’s genius lies in his ability to blend poetic language with a conversational, plainspoken style, giving his lyrics both elegance and relatability. His weathered, soulful voice further enhances the song, imbuing the narrative with authenticity. The Pilgrim is portrayed as a “walkin’ contradiction, partly truth and partly fiction,” a figure who embodies both rebellion and regret while stubbornly chasing his dreams despite the cost.
The title seems to nod to The Pilgrim’s Progress, a Christian allegory, though Kristofferson’s Pilgrim measures progress through a very different lens—one shaped by defiance, loss, and self-discovery. The mysterious “Chapter 33” suggests an ongoing story, leaving listeners to ponder the Pilgrim’s journey beyond the song’s end.
Ultimately, “The Pilgrim, Chapter 33” resonates because it captures the universal struggle between ambition and contentment, triumph and heartbreak. By its conclusion, listeners intimately understand the Pilgrim’s trials, even if his name remains unknown.
Lyrics
See him wasted on the sidewalk in his jacket and his jeans,
Wearin’ yesterday’s misfortunes like a smile
Once he had a future full of money, love, and dreams,
Which he spent like they was goin’ outta style
And he keeps right on a’changin’ for the better or the worse,
Searchin’ for a shrine he’s never found
Never knowin’ if believin’ is a blessin’ or a curse,
Or if the goin’ up was worth the comin’ down
He’s a poet, he’s a picker
He’s a prophet, he’s a pusher
He’s a pilgrim and a preacher, and a problem when he’s stoned
He’s a walkin’ contradiction, partly truth and partly fiction,
Takin’ ev’ry wrong direction on his lonely way back home.
He has tasted good and evil in your bedrooms and your bars,
And he’s traded in tomorrow for today
Runnin’ from his devils, lord, and reachin’ for the stars,
And losin’ all he’s loved along the way
But if this world keeps right on turnin’ for the better or the worse,
And all he ever gets is older and around
>from the rockin’ of the cradle to the rollin’ of the hearse,
The goin’ up was worth the comin’ down
He’s a poet, he’s a picker
He’s a prophet, he’s a pusher
He’s a pilgrim and a preacher, and a problem when he’s stoned
He’s a walkin’ contradiction, partly truth and partly fiction,
Takin’ ev’ry wrong direction on his lonely way back home.
There’s a lotta wrong directions on that lonely way back home.Advertisement
