"Apples and Oranges" was supposed to keep Pink Floyd's commercial momentum going. Instead, it was the death knell for Syd Barrett's tenure in the band.

Their No. 6 U.K. smash debut The Piper at the Gates of Dawn had followed a pair of stand-alone U.K. hit singles, "Arnold Layne" and "See Emily Play." Suddenly, Pink Floyd's label was thinking about the group's career in commercial terms. The Christmas shopping season was ahead, preceded by their initial shows in the U.S.

This put additional strain on the already-faltering Barrett, as did the song's lengthy gestation period.

"Apples and Oranges" took inspiration from everyday life: Barrett wrote the rare Pink Floyd love song after noticing an attractive shopper while walking across Barnes Common. But the band's attempt to complete work on the track became a four-day slog. Pink Floyd's final session reportedly went on for more than 13 hours.

By the time it was over, they'd created a shambolic curio from the psychedelic era, filled with plenty of musical distractions but sometimes making very little sense. In this way, Barrett's disintegrating private life was becoming increasingly echoed in his work.

He gamely tried to talk up the single. "It's a happy song, and it's got a touch of Christmas," Barrett told the U.K. industry magazine Top Pops and Music Now. "It's about a girl I saw just walking around town." But "Apples and Oranges" sank without a trace after it arrived in the U.K. on Nov. 17, 1967; it was never even released in the U.S.

The problem was in making "another attempt to create a hit," Nick Mason admitted in Inside Out: A Personal History of Pink Floyd. "This was another of Syd's whimsical compositions – and it would have made a great album track, but it was probably not really suitable for the job. However, under pressure, we tried to turn it into a hit, with [producer] Norman Smith's help, adding overdubbed choruses and echoes."

Roger Waters took more direct aim at Smith. "A group decision, we definitely set out 'Apples and Oranges' as a single," Waters lamented in Saucerful of Secrets: The Pink Floyd Odyssey. "We all thought it was a really good song, but the recording didn't come up as well. 'Apples and Oranges' was destroyed by the production. It was a fucking good song."

Watch Pink Floyd's 'Apples and Oranges' Video

In reality, there was only so much any producer could have done with "Apples and Oranges" or with Barrett, for that matter. Playing an out-of-tune guitar, Barrett pushes the song faster and faster before leading everyone through an utterly aimless middle eight. Everyone seems to be reaching for the fizzy wit of the Beatles' contemporaneous Sgt. Pepper’s Lonely Hearts Club Band – especially when they exclaim, "We thought you might like to know!" – but there's no discernible hook to ground things.

"It's possible there was a certain amount of U.S. pressure to release it to tie in with our tour," Mason said in Inside Out. "This was a case of trusting the advice we were given, and learning that sometimes – if not always – it was best to stick with our own instincts and make our own decisions."

Melody Maker caught up with a typically nonchalant Barrett, not long after the single stiffed. "Couldn't care less," he blithely replied. "All we can do is make records which we like. If the kids don't, then they won't buy it."

He'd lobbied instead for Pink Floyd's next single to be "Jugband Blues," the product of another disorganized session in which members of the local Salvation Army band had been told to "play whatever they want." It was becoming frightfully clear how close Barrett was to the edge.

They set off on the ill-judged U.S. tour anyway, with scheduled stops on American Bandstand and the Pat Boone Show where Pink Floyd was to lip-sync to "Apples and Oranges." Their appearance with Dick Clark was odd but not disastrous. Barrett either refused or forgot to mouth some of the words. Boone's studio audience, however, would see a much different scene unfold.

"We were taping the show, and he would do the run-through and Syd would stand with his Telecaster with silver bits all over it and mime happily," Waters said in 2011's Pink Floyd: The Early Years. But when the cameras turned on for an official take, a dazed-looking Barrett wouldn't participate at all. "He knew perfectly well what was going on," Waters argued. "He was just being crazy. They did four or five takes like that. Eventually, I mimed it."

They got through the taping, but this kind of deception simply wouldn't work onstage. When Barrett spent an entire concert at the Fillmore West de-tuning his guitar, the U.S. tour was promptly cut short. Pink Floyd's label then refused to release the follow-up single, "Vegetable Man," and David Gilmour joined the band not long after. They hustled out a video for "Apples and Oranges," filmed without Barrett. Waters again lip-synced the words amid brief glimpses of Gilmour, who didn't play on the single.

Barrett never recorded anything else of substance with Pink Floyd. (They ended up putting "Jugband Blues" on Gilmour's debut album with the band, 1968's A Saucerful of Secrets.) Instead, Barrett departed with a final enigmatic muttering as the stereo mix of "Apples and Oranges" fades out: "I'll explain it all to you sometime, one day."

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