Few things showcase the late 1960s generation gap like Skidoo. A great place to start when commenting on this attempt made by middle aged men to connect with a thriving new youth culture is the film’s trailer. It begins with one of the most prominent faces of the era, Timothy Leary, saying, “I just saw a funny movie the other night.” Leary, by the way, has no role in the film, not even a cameo.

For those who don’t know, Timothy Leary was a former Harvard clinical psychologist who gained recognition for studying LSD and praising its effects. After being fired, Leary began appearing before mass crowds of hippies while tossing out catchphrases like “turn on, tune in, drop out.” He spent a portion of his life on the run after breaking out of a California prison during a ten year sentence for the possession of two joints. While on the run, Richard Nixon labeled him “the most dangerous man in America”, making him a boogeyman for his war on drugs.

If the goal was to attract a younger audience, you couldn’t find better bait than Timothy Leary.

The attempt to combine two different generations makes Skidoo such a bizarre relic to take in all these years later. It’s a movie from Paramount Studios where you feel the people who brought you White Christmas and The Ten Commandments are now looking at their surroundings like a foreign planet, unclear how to sell themselves to an audience they have nothing in common with. Its director, Otto Preminger, was one of the most established directors throughout the ’40s and ’50s with films like Laura and Anatomy of a Murder.

Along with a director who worked with every A-lister imaginable, this hippie/LSD themed film stars Jackie Gleason, someone who was one of the first notable faces on television while starring on The Honeymooners. Gleason also made a successful transition into film with an Academy Award nominated performance in The Hustler. The transition was surprising because at the time Hollywood was under the firm belief movie audiences would never pay to see a face they got on their television for free. Since The Hustler has been credited for creating a pool resurgence in the 1960s, that belief was proven to be incorrect.

Alongside Gleason are Groucho Marx and Mickey Rooney, two performers who were so aligned with the past they made their names on the vaudeville circuit. To be fair though, Groucho had many fans within this younger generation due to the rebellious, surreal sense of humor found in the Paramount Marx Brothers films like Duck Soup and Horse Feathers.

These established names from an older generation are part of a film where, in the trailer, Timothy Leary says, “It’s a movie that, uhh, kids will like, they turn on the older generation, get them high. Can you imagine Groucho Marx playing God?”

After Timothy Leary’s endorsement, another performer old enough to have performed on the vaudeville circuit, Sammy Davis, Jr., turns up in the trailer and says, “It is the gassiest, grooviest, swinginest, trippiest movie you’ve ever seen.” Just like Leary, Sammy Davis, Jr. has no role or cameo in Skidoo. But even without a part, Davis was the perfect spokesman for Skidoo because like everyone involved, he was an older name trying to connect with a younger generation.

Case in point, while being someone who once performed in a relatively straight-laced group like The Rat Pack, Davis was in the process of reinventing himself by hanging in the same circles as Church of Satan founder Anton LaVey. The most entertaining example of Sammy Davis, Jr. successfully inserting himself where the culture was at the time is landing Deep Throat’s Linda Lovelace in his entourage. According to Linda Lovelace in her 1980 autobiography Ordeal, after fooling around with Davis multiple times, he asked her how to deep throat, and then surprised her abusive husband, Chuck Traynor, by performing the act on him. I’ll avoid any further derailment by suggesting you refer to the Dangerous Minds article titled “Revenge Porn: That Time Linda Lovelace Taught Sammy Davis, Jr. How To Deep Throat…Her Husband.”

Hopefully that tangent gives you an idea of the culture change taking place that birthed a film like Skidoo. Unpredictable box office hits like Easy Rider and Deep Throat hadn’t happened yet, but the culture was ready and waiting. We’ve never before or since seen a decade that dramatically changed like the 1960s did. A decade that began with family friendly hits like The Music Man and The Absent-Minded Professor in 1962 soon found itself upside down in 1968 when the box office phenomenon was Rosemary’s Baby. Someone who appears in Skidoo, Frankie Avalon, cute and trendy just a few years prior, found his teen idol style feeling like it belonged in a time capsule in 1968.

Here are the more interesting tales about Skidoo pulled from sources like IMDB Trivia, where you never know what’s fact or fiction.

  • Instead of Harry Nilsson who gives Skidoo an interesting sound (with tracks like a concluding theme that names everybody who worked on the film), Otto Preminger wanted Bob Dylan to score Skidoo. Dylan saw the film and declined because he felt it was a disaster. He then said he’d reconsider on one condition: that he and his wife be left alone in Preminger’s Hollywood mansion to watch the film a second time. Preminger did as requested, and instead of reconsidering, Dylan and his wife walked around Preminger’s mansion jotting down décor choices they liked and could use in their home.
  • The boat used for God’s yacht in the film was owned by John Wayne, who starred in Preminger’s film, Harm’s Way. Nothing says generation gap like anything related to John Wayne mixing with hippie culture.
  • Otto Preminger experimented with LSD to prepare for Skidoo. Groucho Marx also experimented with LSD. It would be the subject of an article titled “My Acid Trip with Groucho” written by Paul Krassner.
  • Groucho Marx was 78 at the time, and had to be somewhat bullied into wearing his traditional mustache greasepaint by Otto Preminger. Preminger also allegedly berated Groucho on set, and Jackie Gleason was so angered by it he physically threatened Preminger.
  • Skidoo would be the final film Groucho Marx worked on, and from here on out the only time you’d see him was as a guest on The Dick Cavett Show, usually accompanied by a notorious presence during his final years: his secretary/girlfriend, Erin Fleming. Being someone who, after committing suicide, had a headstone with Groucho Marx’s infamous quote “Hello, I must be going” written on it, it won’t be surprising to hear Fleming was mentally unstable. If you love old Hollywood gossip and books, I highly recommend one written by someone who was there to witness Groucho’s years with Erin Fleming, Raised Eyebrows by Steve Stoliar.
  • Rob Reiner was an uncredited writer who gave the hippie characters more authentic lines than were used in earlier drafts. According to what’s told, Preminger fired and re-hired him daily.
  • It can’t be stressed enough how this film had many ties to an ancient Hollywood system. One example is Faye Dunaway being under contract to Otto Preminger back when directors and actresses still had this odd business arrangement. She refused to appear in Skidoo after her success in Bonnie and Clyde, something credited with kickstarting the New Hollywood era. She was sued by Preminger, and the matter was settled out of court.
  • Skidoo stars three actors who portrayed Batman ’66 villains, Frank Gorshin (Riddler), Burgress Meredith (Penguin), and Cesar Romero (Joker). Along with being a Batman ’66 fan, I’m also a Gilbert Gottfried’s Amazing Colossal Podcast fan, which means I have to mention Cesar Romero allegedly having boy toys throw orange wedges at his ass.
  • Batman ’66 fans will also recognize Skidoo being directed by one of three men who portrayed Mr. Freeze on the series.

We could talk all day about the moment in history Skidoo hails from, but some of you might be wondering how it plays. If you take its historical importance out of the equation, Skidoo would certainly be considered a bad movie. It didn’t find fans in 1968, and to this day it doesn’t have the type of cult audience something like Valley of the Dolls was rewarded with.

The film follows Jackie Gleason as Tony Banks, a former gangster called back in by a crime boss referred to as God (Groucho Marx) to sneak into a prison and kill a former employee who’s ratting on the operation, “Blue Chips” Packard (Mickey Rooney). As this gangster plot plays out, on the side you have Carol Channing housing hippies her daughter befriends. All these years later it’s one of the more fascinating messes. In one frame you’ll see someone as traditional and square as Jackie Gleason and then before you know it you’re in a bus where women are being stripped down and having their bodies painted.

I agree with Timothy Leary when he says Skidoo will get you high, because by the end of it as Carol Channing runs around on a boat dressed like a Revolutionary War patriot singing the theme, my brain drips out of my ears as I look around in confusion.

Watching Jackie Gleason in the middle of an LSD trip pinching imaginary objects and seeing a screw with Groucho Marx’s head on top of it floating around his jail cell is peak absurdity. Along with this, LSD trips involving a naked football team, and a sentient trash can musical number, Skidoo contains the type of confusion only middle aged men attempting to appeal to a generation they find frightening can offer.

If you’re someone who appreciates the history of entertainment, Skidoo is a must watch. The film’s existence is reminiscent of the environment explored in Once Upon A Time In Hollywood. Similar to what Rick Dalton feels to be true about himself, there are so many names associated with this film who had their finger on the pulse in 1962 suddenly finding themselves labeled dinosaurs by a younger generation. There’s an exciting sense of confusion to be found while watching former icons attempting to stay on top while ambitious blockbusters like The Graduate are causing an industry to question everything they knew.

In the immortal words of Sammy Davis Jr in Skidoo‘s trailer, “Anybody who don’t like that daddy don’t like chicken on Sunday.”


  • Emilio Amaro

    Outside of writing about movies, Emilio’s interests include watching Gilmore Girls, sharing gossip about Paul Lynde and admiring the work of beloved character actor Phil Fondacaro. Amaro Emilio