As R.E.M. were completing work on their eighth studio album, Automatic for the People, in the late spring of 1992, the quartet’s members grew concerned about the final track listing. For the most part, this was a batch of dark songs about difficult subjects. Perhaps a bit of levity, in the form of the buoyant “The Sidewinder Sleeps Tonite,” would be welcome in the running order.

“We included this song on Automatic in order to break the prevailing mood of the album,” guitarist Peter Buck wrote in the liner notes for In Time: The Best of R.E.M. 1988-2003. “Given that the record dealt with mortality, the passage of time, suicide and family, we felt that a light spot was needed. In retrospect, the consensus amongst the band is that this might be a little too lightweight.”

Like the majority of the songs on this album, “Sidewinder” first came to life in rehearsal/demo sessions conducted by the instrumentalists in the band: Buck, bassist/keyboardist Mike Mills and drummer Bill Berry. Following a couple months of promotion for 1991’s Out of Time, the trio holed up in R.E.M.’s hometown of Athens, Ga., and began working on what they had planned to be a big rock record. But the tracks that most intrigued them – and singer Michael Stipe – turned out to be the quieter, acoustic-driven ones, and the melancholy music that would symbolize Automatic for the People started to coalesce.

But amid some of the softer, slower, minor-key stuff was an upbeat boogie, created the same day that the men came up with the music for “Man on the Moon.” Both were melody-forward, but the former seemed to recall R.E.M.’s sunniest moments, such as “Shiny Happy People” and “Stand.” It only became bolder with John Paul Jones’ string arrangement, added after the bulk of the album sessions in Atlanta.

“The other guys gave me this new song that is so beyond ‘Stand’ that it makes ‘Stand’ sound like a dirge,” Stipe told Melody Maker in 1992, perhaps referring to what would become “The Sidewinder Sleeps Tonite.” “I mentioned it and they all started laughing. But it sounds like that song ‘The Sound of Philadelphia’ by MFSB. It’s really out there.”

R.E.M’s singer went “really out there” in penning the lyrics to “Sidewinder,” writing lines that list food (“A can of beans or black-eyed peas / Nescafe and ice”) or could be snippets of overheard conversation (“Uou can’t lay a patch by computer design / It’s just a lot of stupid, stupid signs”) or obsess over the tiny details (“There are scratches around the coin slot”).

But that’s not to say that this song isn’t sub-sub-sub-substantial. “Sidewinder” seems to be offering glimpses of a transient lifestyle with the hallmarks of a roadside motel – instant food, strange characters and pay phones. Although Stipe wrote the lyrics, the details may have mirrored aspects of guitarist Buck’s life, seeing as his first marriage was in trouble during the Automatic era.

“I didn’t even have a house,” he revealed in the documentary R.E.M. by MTV. “I was driving around listening to cassettes and staying in $19-a-night motels.”

The “Sidewinder” mentioned in the song's title is a snake, perhaps a metaphor for the drifting narrator, or maybe it refers to the public phone that is so central to the lyrics. Some old-timey telephones were called sidewinders, because of the coil of cord that wound on the side of the machine.

It’s also possible that in the chorus (where Stipe squeezes nine syllables into the space of four, “callmewhenyoutrytowakeherup”), the “her” that he’s singing about could refer to the phone. If cars, boats and spaceships can be “shes,” why can’t a pay phone be a “her”?

Despite wearing a lighter pallor, “Sidewinder” still ties into one of Automatic’s main themes: youth, or rather, memories of youth. You can hear Stipe laugh as he sings, following the namecheck of Dr. Seuss (because he’s incapable of saying the children’s author’s name as Dr. Zeus). He goes on to sing about the Cat in the Hat and cartoons, in a lyric of which the singer is particular fond.

“Sidewinder” “holds on of my favorite lines ever, in ‘their world has flat backgrounds and little need to sleep but to dream’,” he wrote in the liner notes to Part Lies, Part Heart, Part Truth, Part Garbage 1982-2011. “Cartoon characters never just get sleepy, they always have to have a dream of some floaty kind.”

In the recording stage, the song’s working title was “Wake Her Up,” before it was changed to “The Sidewinder Sleeps Tonite” – a reference to the old Tokens’ doo-wop hit “The Lion Sleeps Tonight.” Stipe even cops that song’s “eee-dee-dee-dee” intro in the R.E.M. song’s opening moments. The guys had a genuine love for the song, which they had been covering since R.E.M.’s earliest shows, and decided to clear their nod to the pop classic with its songwriters.

“We actually paid them for that,” Buck revealed in 1992. “We didn’t want some guy, down the road, going, ‘You owe me two million dollars.’ So we called them up and said, ‘We’re calling it “The Sidewinder Sleeps Tonite” and the singer kind of paraphrases the line.’ In any court of law, we couldn’t have been nailed. Because the song doesn’t have anything to do with it. But you don’t want someone to feel that you’re stealing from them.”

R.E.M. also promised to cover “The Lion Sleeps Tonight,” allowing Stipe to squeal with joy on the B-side of the “Sidewinder” single, thus ensuring the songwriters some royalties. Which is what happened when the band put out the song as Automatic’s third single in the winter of 1993, a few months after the album’s release. It kind of flopped in the U.S. ("Sidewinder" fared well on rock radio, but didn’t match the reaction to “Drive” or “Man on the Moon”), but went to No. 17 in the U.K.

Although “The Sidewinder Sleeps Tonite” has featured on multiple best-of compilations – including 2003’s In Time and 2011’s career-spanning Part Lies, Part Heart, Part Truth, Part Garbage – R.E.M. never played the song in concert. It is one of only two tracks from Automatic for the People to never make it into a concert (the other being “New Orleans Instrumental No. 1”).

“That’s a song that to this day I’m not really sure what it’s about, but it’s a lot of fun,” Mills told Stereogum in 2007. “We never do it live, but it’s a good record. It’s just one of those songs that never seemed like it need to be done live. We might’ve messed around with it at sound check a couple of times, but it never felt like something we should really try.”

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