The Pilgrim: Chapter 33 (Hang In, Hopper) Lyrics

See him wasted on the sidewalk in his jacket and his jeans,
Wearing yesterday's misfortunes like a smile.
Once he had a future full of money, love, and dreams,
Which he spent like they was going out of style,
And he keeps right on a'changing for the better or the worse,
Searching for a shrine he's never found,
Never knowing if believing is a blessing or a curse,
Or if the going up was worth the coming 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 walking contradiction, partly truth and partly fiction,
Taking every 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.
Running from his devils, Lord, and reaching for the stars,
And losing all he's loved along the way.
But if this world keeps right on turning for the better or the worse,
And all he ever gets is older and around,
From the rocking of the cradle to the rolling of the hearse,
The going 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 walking contradiction, partly truth and partly fiction,
Taking every wrong direction on his lonely way back home.
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Cover art for The Pilgrim: Chapter 33 (Hang In, Hopper) lyrics by Kris Kristofferson

You're partly right. In one(?) version of this song, Kristofferson starts out by saying, to the background of his guitar, that he "started writing this song about Chris Gantry, ended up writing about ...(?) and Johnny Cash..." then goes on to mention several other country/folk singers of the time such as Ramblin' Jack Elliot. This song is about so much more than anyone in particular. A lot of what you said was right, but I see it as Kristofferson personifying the whole genre of music in this song. I also love the imagery of "wearing yesterday's misfortunes like a smile". It's so resonate to anyone who's been known to hit the booze hard (and often subsequently the sidewalk). This was one of the songs that made me fully appreciate the poet in Kristofferson. I mean, one can dissect this like a poem with its binary opposites, use of repetition, alliteration..... but I won't, I promise. Frankly, I'm a bit disappointed with the lack of enthusiasm for this song. Oh well.

Cover art for The Pilgrim: Chapter 33 (Hang In, Hopper) lyrics by Kris Kristofferson

Kris wrote this song about Johnny Cash, his good friend and fellow Highwayman. It talks about Johnny's contradictory stance as being full of the gospel while also being indulgent, doing drugs, and having an obvious dark side to him. I don't think this was meant to be like a diss, because Kris and Johnny were friends and it's not too harsh. But it's definitely about Mr. Cash.

@KickerOfElves Kris has said on a number of occasions that the line "He's a walking contradiction, partly truth and partly fiction" was written about Cash.

Cover art for The Pilgrim: Chapter 33 (Hang In, Hopper) lyrics by Kris Kristofferson

Other names Kris mentions are Dennis Hopper, Norman Norbert, Funky Donnie Frit?, Billy ?Swan?, Bobby Newerht, Jerry Jeff Walker, and Paul Seable.
I think Willie Nelson does the definitive version of this song on Willie Sings Kristofferson, a great and under-appreciated album, btw.

@Runnin

Funky Donnie Fritts and Billy Swan have been with Kris from his early days in Nashville. Billy wrote the huge 1960s Clyde McPhatter hit "Lover Please" when he was still in High School and had a huge 2nd hit that he sang himself, "I Can Help", about a dozen years later.

Donnie and Kris who have been together forever and were drunk when they first cut "Me and Bobbi McGee" to tape after they left a bar {Tally Ho Tavern? Yes, the Tally Ho was a real place.} and went to a studio that one...

Cover art for The Pilgrim: Chapter 33 (Hang In, Hopper) lyrics by Kris Kristofferson

This song is about the musician lifestyle. Norman Norbert, Donnie Frits, Billy Swann all played in Kris's 1970s band. Paul Siebel was a Dylanesque singer/songwriter who quit music after his third album, his best known song is "Louise" covered by Bonnie Raitt.

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