Some interesting facts about this song that I just learned:
Kristofferson was influenced by Fellini's La Strada.
The impetus for the song was a writing assignment given to Kristofferson by his new song publisher, Fred Foster, when Kris said he was having a dry spell. Foster told him to write something with an "On the Road" concept about me and Bobby McKee, a secretary at the publishing company.
At the time, Kris was flying oil workers out to rigs in the Gulf of Mexico via helicopter during the week, then flying back to Nashville on the weekends to work on his musical career. The song basically came while he was flying around Baton Rouge and New Orleans.
From the new book, Outlaw: Waylon, Willie, Kris and the Renegades of Nashville. Tanks to Paul Wiener for letting me know about it.
February 1959. Buddy Holly and the Crickets are touring with Ritchie Valens and the Big Bopper. Holly hires a four-seat airplane to take his band to Fargo, North Dakota. The Big Bopper has a cold, so one of the Crickets, Waylon Jennings, offers him his seat on the plane. A few minutes later, Holly, Valens and the Big Bopper would be dead, the plane crashing in snow shortly after take-off.
In 1965, after struggling a few years with grief and guilt, Jennings headed to Nashville, where he eventually made it as a country singer. But he grew increasingly frustrated with the stuffy attitudes and limited artistic freedom in Music City USA. Along with another rebellious Texan named Willie Nelson, he rejected the "rhinestone suits and new shiny cars" of the slick Nashville scene and began experimenting with a new sound.
By the early 1970s, Jennings and Nelson had started blending a rock and roll sensibility with the country tradition of Hank Williams, Bob Wills and Johnny Cash. It was an edgier form of country, musically stripped down and lyrically more complex, and it became known as "progressive country" or the Outlaw movement. One of the influences on the new sound was Johnny Cash's own friendship and musical exploration with Bob Dylan in the late 1960s. Dylan wrote "Wanted Man" for Cash, who included it on his 1969 live album, At San Quentin. (Real outlaw music.) And, of course, Dylan himself was greatly inspired by Hank Williams. So, it shouldn't have been a surprise when Dylan went country. Or when country went Dylan.
Or when one of Buddy Holly's Crickets dug back into his rock and roll roots to lament what Nashville had become.
Here's Waylon in 1975, singing what became a kind of anthem for the outlaw country movement: "Are You Sure Hank Done It This Way?"
Lord, it's the same old tune, fiddle and guitar Where do we take it from here? Rhinestone suits and new shiny cars It's been the same way for years We need to change
Somebody told me when I came to Nashville Son, you finally got it made Old Hank made it here; we’re all sure that you will But I don't think Hank done it this way I don't think Hank done it this way
Ten years on the road, making one night stands Speeding my young life away Tell me one more time just so I'll understand Are you sure Hank done it this way? Did Ol' Hank really do it this way?
Lord, I've seen the world with a five piece band Looking at the back side of me Singing my songs and one of his now and then But I don't think Hank done 'em this a'way I don't think Hank done 'em this a'way
