“The Pilgrim, Chapter 33” isn’t just a song—it’s a deeply personal anthem about life’s struggles, redemption, and the search for meaning. Kris Kristofferson, known for his raw, poetic songwriting, pours his heart into this track. It’s a tribute to those who’ve lived with intensity, stumbling through both highs and lows, often lost but always chasing something more.
At its core, this song tells the story of a person who’s made mistakes but never let them define him. He’s been knocked down, but he keeps getting up, with a sort of defiant resilience that Kristofferson captures so beautifully. It feels like a quiet salute to the dreamers and drifters, the people who don’t fit the mold but have an undeniable passion for life.
You can hear the ache in Kristofferson’s voice as he sings, and it’s hard not to get swept up in the emotion of it all. The lyrics “He’s a poet, he’s a picker, he’s a prophet, he’s a pusher” paint a vivid picture of a man who is many things at once—flawed, misunderstood, but also brilliant in his own way. There’s a universality here that strikes a chord, especially for anyone who’s ever felt like they don’t quite belong, yet keep pushing forward.
One of the most touching aspects of this song is how it reflects Kristofferson’s own journey—he’s said the song was inspired by his own experiences and those of people he’s met along the way. In a sense, “The Pilgrim, Chapter 33” feels like Kristofferson’s way of reminding us that life is messy, but that’s where its beauty lies.
This song reminds us that no matter how many times we fall, as long as we’re still moving, we’re still pilgrims on the journey.
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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.