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Introduction
Some songs aren’t just written; they’re lived. “The Pilgrim, Chapter 33” by Kris Kristofferson is one of those rare gems that captures the raw essence of a complicated man, one who’s both broken and beautiful, lost and found, reckless and reflective. It’s more than just a melody strummed on a guitar—it’s a poetic portrait of what it means to be a restless soul, eternally wandering in search of something that may never be found.
This song is Kris Kristofferson at his storytelling best. It’s the kind of piece that makes you feel like you’re sitting with him on a quiet, rainy evening, sharing stories and secrets, with the smoke of a cigar swirling around. Each verse is like a snapshot of the people he’s encountered along his own journey: dreamers, drifters, lovers, and fighters. It’s a salute to all the misfits, to those who don’t quite fit into neat boxes, who live life on their own terms.
The story behind the song makes it even more compelling. Kristofferson penned it as a tribute to his close friend and fellow songwriter, Johnny Cash, and to the countless others who straddled the line between greatness and ruin. It’s said that Kristofferson saw a bit of himself in every word he wrote. The “pilgrim” in the title is more than just a character—it’s a composite of Kris himself and the men he admired, men who walked the tightrope between their virtues and vices, battling the best and worst parts of themselves.
Lyrically, the song is packed with lines that cut deep, leaving you pondering long after the last note fades. Phrases like, “He’s a poet, he’s a picker, he’s a prophet, he’s a pusher,” are so vivid they almost jump off the page. It’s a whirlwind of contradictions, just like the person it’s describing. There’s a sense of melancholy woven into each verse, but there’s also a sense of admiration—a respect for those who dare to live authentically, no matter how messy or misunderstood their lives may seem.
Musically, “The Pilgrim, Chapter 33” is straightforward yet soulful. It has a folk-country feel that’s all about the storytelling, with a soft strum of acoustic guitar guiding the way. There’s nothing overly flashy about it, but that’s what makes it hit even harder. The simplicity lets the words take center stage, allowing every nuanced emotion to shine through.
Listening to “The Pilgrim, Chapter 33” feels like reading a weathered, dog-eared book filled with lines that tell the story of a thousand lifetimes. It’s about the unglamorous side of life, about grit and grace, pain and perseverance. In the end, it’s a celebration of the human spirit—the good, the bad, and everything in between. It’s a song that sticks with you, like a friend’s wisdom whispered in your ear when you need it the most.
Video
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.