About The Song
Kristofferson writes with such emotional insight that you have to believe that he saw a lot of himself in the character as well. As he told CMT in a 2007 interview, “Well, there were a lot of people that the pilgrim stood for or that I felt fit into that category, and most of them were people who were serious about songwriting, but an awful lot of us just looked like we were out of work.”
Like all great songwriters, Kristofferson knows just how important those first lines are, so he delivers an opening couplet here that combines telling details with a searing simile to let us know exactly what this Pilgrim is all about: “See him wasted on the sidewalk in his jacket and his jeans/ Wearin’ yesterday’s misfortunes like a smile.” With the scene so effectively set, he can go about telling the rest of the story, how this outlaw has seen better days but forges on nonetheless “searchin’ for a shrine he’s never found.”
One of the hallmarks of Kristofferson’s best songs is his ability to make his poetics seem effortless and plainspoken, while his scratchy, deep voice adds an extra patina of integrity to seal the deal. What makes “The Pilgrim” so effective is his ability to both romanticize the character’s rebellious stance without skimping on the damage that he’s done to himself: “Runnin’ from his devils, Lord, and reachin’ for the stars/ And losin’ all he’s loved along the way.”
Kristofferson suggests that the character ultimately doesn’t regret his decisions, especially in the final verse when he sings, “The goin’ up was worth the comin’ down.” In the chorus, Kristofferson demonstrates just how much of a “walkin’ contradiction, partly truth and partly fiction” this guy is, using the timbre of his vocal to vacillate between the better angels and the pesky demons that accompany The Pilgrim at every step while he’s “Takin’ every wrong direction on his lonely way back home.”
The title of the song seems a play on the Christian allegory The Pilgrim’s Progress, Kristofferson’s implication being that this guy measures progress in a much different way than the pious. Why he decided that this particular snapshot was “Chapter 33,” well there’s some mystery for you. As for the identity of “The Pilgrim,” it matters not, because Kristofferson’s portrait of him is resonant enough that we know his triumph and heartbreak by song’s end, even if we don’t know his name.
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.