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  • Acclaimed Flop: It was badly received upon release, partially because nobody expected The Monkees to star in such a Mind Screw of a film, but is now a respected work. Not only have people have come to appreciate its weirdness, but the subsequent fame of Bob Rafelson and Jack Nicholson certainly helped. And of course, the Monkees have been Vindicated by History.
  • Acting for Two: June Fairchild is one of the belly dancers in the "Can You Dig It?" segment and also the bikini-clad woman who threatens to jump from the building.
  • Box Office Bomb: Budget, $750,000. Box office, unknown but almost certainly under $100,000 note . The combination of a "TV rock band" considered past its prime, plus the bizarre Mind Screw of a film that director Bob Rafelson and co-writer Jack Nicholson put together led to Columbia Pictures burying the movie. It played in a handful of big city theaters at the end of 1968, went on the Drive-In Theater circuit after that, and was forgotten afterwards, but became a Cult Classic in The '80s when The Monkees experienced a resurgence in popularity.
  • Creator Backlash: Of a minor sort. Peter Tork stated his main complaint with the film is the ending and message "seemed to indicate you can't get out of the box."
  • Creator Couple: Lady Pleasure, who kisses all of The Monkees, was played by Mimi Machu (under her Stage Name of I.J. Jefferson), who was the girlfriend of screenwriter Jack Nicholson at the time.
  • Creator Killer: The film was the beginning of the end for The Monkees. It's been speculated by some (including the band) that Bob Rafelson and Bert Schneider made the film purely to Torch the Franchise and Run.
  • Deleted Scene: The shooting script had a lengthy Jidaigeki parody scene where the Monkees battle a Samurai warlord named Godzilla (sometimes misreported as them actually battling the Godzilla). It was slated to be shot on-location in Japan, but never got filmed for budgetary reasons. See more here and here.
  • Dueling Works: To a certain extent with Magical Mystery Tour, both being plotless surreal musical comedies starring a popular rock band. Head's initial screenplay draft (back when it was still called Changes) was submitted in mid-December of 1967, just before MMT debuted. Davy Jones actually saw the original broadcast of MMT while visiting his family in England for Christmas.
  • Fake Nationality: The Swami is presumably supposed to be from India, but he's played by Abraham Sofaer, who was born and raised in British-controlled Burma in a family of Iraqi Jewish descent.
  • He Also Did:
    • Not only did Nicholson write the screenplay (during the brief pre-Easy Rider period when he was trying to transition away from acting to writing and directing), he also assembled the soundtrack album.
    • That chiming electric guitar part on "As We Go Along"? Played by Neil Young.
  • Keep Circulating the Tapes/Vindicated by Cable: After its brief run in theaters Head was almost impossible to see. For a long time a couple late night airings on CBS in The '70s were the only exposure it got in the US. Around the time of the 1986 Monkees comeback it was released on VHS and had a run in specialty movie theaters. Numerous airings on TBS and TNT in The '90s finally gave it a wide audience.
  • Missing Trailer Scene: This trailer, titled "NY Action", consisted entirely of shots that didn't make it to the finished product, including glimpses of offcuts and clapperboards.
  • Reality Subtext: The "box", shown in several scenes, was inspired by the lounge area built for The Monkees during the filming of their television show. Between takes, they grew bored and wandered around the studio, often getting lost, so Screen Gems brass added a special room next to the soundstage. They would spend time there studying their scripts, composing, and playing music, and smoking (which they were forbidden to do on the set). Colored lights were added to the room to page whomever was needed on the set.
  • Stillborn Franchise: Had the film been a hit, it would have received a follow-up, if not a direct sequel, which would have used the tag line "From the producers who gave you Head."
  • What Could Have Been:
    • The part of Lord High 'n' Low was written for Bruce Dern. In fact, the character was originally called Dernsie. However, having a classic Large Ham like Timothy Carey in the role probably fit the film's oddball tone better.
    • Michael Nesmith was slated to write the score at one point.
    • Michael was also originally supposed to do the song-and-dance number, with his song "Magnolia Simms" (from The Birds, The Bees and The Monkees) actually mentioned by name in the first draft of the script for the scene. Then Michael later recommended Harry Nilsson's "Daddy's Song" for the scene to Bob Rafelson, and even recorded a vocal for it, but Rafelson ultimately decided to make the scene a Davy showcase (while keeping the song).
  • Working Title: It was originally going to be called Changes, but right after filming began they found out there was another movie with that title already in production. After that it was variously called Untitled, Movee Untitled, and DASturb, with Head being chosen almost at the last minute. Changes eventually became the title of the last Monkees album before their 1970 breakup (after being reduced to a Davy-Micky duo).
  • Writing by the Seat of Your Pants:
    • The initial stage of the film's script was just The Monkees, Jack Nicholson and Bob Rafelson spending a weekend at a resort in Ojai, California, getting stoned and spouting ideas into a tape recorder. Nicholson then shaped all the ramblings into a surprisingly-organized screenplay, though a bunch of changes happened during filming, including whole sequences that got dropped.
    • Ken Thorne (who'd scored Help!) was brought in very late in post-production to write the score.
  • You Look Familiar: Several performers who appeared in the TV series have roles here. Vito Scotti (the Italian officer who surrenders his tank to Micky in the desert) played Dr. Marcovich in the episode "The Case of the Missing Monkee". William Bagdad (the black sheik in the desert scene) played another Middle Eastern character in "Everywhere a Sheik, Sheik". June Fairchild (the woman who threatens to jump off the building) was the girl who asked Mr. Schneider about teenagers necking in "The Chaperone".

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