In February 1968, American rock band The Monkees were at something of a crossroads. The television series of the same name that had launched their careers was ending (the last episode was due for broadcast on 25 March 1968) and, still riled by repeated claims (still made today by music lovers more interested in specious notions of “authenticity” than in a good tune) that they were nothing more than a manufactured band (again, a ludicrous argument – to one degree or another all bands are manufactured), they were looking for something new to do. The idea of rock bands making films was nothing new though few of them had made much of an impact in the film world. The Beatles had scored huge hits with A Hard Day’s Night (1964) and Help! (1965) of course, but they were exceptional and marvellous though they were, The Monkees were no Beatles.

To help them come up with a film that they hoped would open up a new audience for them (originally pointedly titled Changes, briefly became Untitled before settling on the zeitgeist friendly Head), the band decamped to Ojai in California for the weekend with Jack Nicholson, director Bob Rafelson (who had co-created the TV show with producer Bert Schneider) and, by all accounts, copious amounts of marijuana where the basic points of a plot were hammered out in, presumably, a bit of a daze. Rafelson later claimed that Nicholson took the tape recordings made from the drugged-up, stream-of-consciousness ramblings and, under the influence of LSD, hammered into what passed for a screenplay.

There’s no story here so there’s little point looking for one. It’s merely a kaleidoscopic collection of scenes and vignettes that probably made sense to Nicholson when he pieced it altogether. It starts – as it ends – with The Monkees (Micky Dolenz, Michael Nesmith, Peter Tork and Davy Jones) jumping from the Gerald Desmond Bridge in Long Beach, California during its dedication ceremony and proceeds through a formless but very entertaining stream of movies spoofs (it sends up the conventions of war films westerns, musicals and spy thrillers among others). The band are seen performing live, each member of the band gets a chance to exorcise their angst as they find themselves, trapped, thwarted and frustrated at every turn, until Tork introduces them to a swami he believes to have “the Answer” (a swipe at The Beatles and their time with Maharishi Mahesh Yogi, perhaps?). It all comes to… ahem… a head when they meet a giant Victor Mature and run riot on a studio backlot…

Somewhere in this bewildering but brilliant jumble of images, ideas and songs are some no doubt serious points about all sorts of things (the Vietnam war for example), but mainly it seems to have been about The Monkees themselves and their dissatisfaction with the way their careers were going – fame “was slowly burning a hole through the centre of our brains” Dolenz told The Guardian in 2011 on the eve of one of their reunion tours. It feels like the band themselves were pressing the self-destruct button on their clean-cut television image in search of a counterculture audience which, at best, was apathetic towards them and at worst loathed them for being too mainstream. Tork had other thoughts on the reason why the film was made, musing in the same Guardian interview that “there’s some weight behind the idea that Bob and Bert wanted to wreck the Monkees, to stop it cold in its tracks. I’ve never known for sure. Bert and Bob might have thought out loud: ‘Let’s kill the Monkees!’ Or they may have not thought so out loud but at some unconscious level, they were sick of the Monkees and wanted to do something else.”

Whatever the reason, the film was a mixed bag for the band but has aged rather well. Certainly the trippiness is none-more-1968, but there’s certainly something wonderfully appealing about its wilful weirdness. The songs certainly help, with the excellent Porpoise Song taking home top honours but the self-satirising Ditty Diego (War Chant) (written by Rafelson and Nicholson), Nesmith’s blues-flavoured Circle Sky and Tork’s Long Title: Do I Have to Do This All Over Again? are all excellent tunes that give lie to the claim that The Monkees were a spent force after the TV show ended. The new music alienated some of the band’s established fan base (who were getting older and mainly moving on anyway) but the accompanying soundtrack album, with contributions from Carole King and Harry Nilsson, is one of their best, featuring some of the most mature and interesting songs in their entire catalogue.

But those fans who loved the band for their frothy, knockabout TV personas (anyone who says they didn’t is probably lying…) would have been nonplussed by what they got in Head. There had been times when their small screen adventures had hinted at the wider youth culture revolution brewing on the West Coast but this was a full on “happening”, a psychedelic extravaganza tinged with more politics and self-loathing than most of those fans would have wanted – in a spoof of westerns, Dolenz is hit by a volley of fake arrows and, frustrated, complains to the director, also named Bob, “these fake arrows, and this junk, and the fake trees – Bob, I’m through, it all stinks man!”. It’s a mess, there’s no doubt about that, but it’s a fascinating one all the same and one suspects that a lot of the sentiments expressed in the film were as heartfelt as they are baffling.

None of it makes a jot of sense and may not be any more coherent even under the influence, but it’s still strangely exhilarating. It’s best not to worry too much about what any of it means and instead just take the advice of another 60s beat combo sensation – “switch off your mind, relax and float downstream” (Tork can be heard nonchalantly whistling Strawberry Fields Forever at one point). Not that enough people took that advice in 1968. The film tanked at the box office. It’s been suggested that Schneider and Rafelson chose the title Head because they planned to sell their next film, the already in pre-production Easy Rider (1969), with the tagline “from the guys who gave you Head,” an idea dropped like the proverbial hot potato after the film’s poor box office, bringing in just $16,111 against a budget of $790,000. It was a film which, at the time, simply had no audience. “Most of our fans couldn’t get in because there was an age restriction and the intelligentsia wouldn’t go to see it anyway because they hated the Monkees,” Dolenz told The Guardian.

But over time the film’s stock has risen and today it enjoys a much-deserved cult reputation. The cyclical nature of the plot (The Monkees end up jumping off that bridge again) and the couplet from Ditty Diego (War Chant) “So make your choice and we’ll rejoice, in never being free” suggest that the band were more scared of being forced to repeat the same things over and over for the rest of what careers they may have had and were determined to do whatever it took to break out of the rut, even if it seemed an impossible task. It was a brave effort, but it was the wrong move at the wrong time. It wasn’t helped by a bizarre marketing campaign which inexplicably made no reference to the film featuring The Monkees at all.

It wasn’t the end of The Monkees, though it was the end of their best years together. Tensions had been running high between band members throughout production – Nesmith walked out on the first day in a dispute over pay – and for Tork, who was unhappy throughout filming, it was all too much. After a tour of the Far East in December 1968 and the completion of a television special, 33⅓ Revolutions Per Monkee (1969), he left the band. Nesmith called it a day in 1970 and the band’s golden years came to an end. There were reunions and new recordings from 1987 onwards but it was never quite the same. Head would remain their only big screen outing (though Nesmith was a pioneer of the music video as we know it today, created the much-admired longform video Elephant Parts in 1981 and helped to produce Alex Cox’s cult hit Repo Man (1984)) but today it stands as a flawed but still irresistible monument to a band that may have been put together by television executives but who eventually managed to prove their worth as serious musicians. And they had some killer tunes to boot.