Given enough time, a piece of crap can fossilize and then be polished and put upon the mantel with grace. "Skidoo" is a piece of crap that through the passage of time has become a fascinating cultural artifact. It's not QUITE ready to be put on the mantel but at least I can watch it without need of a suicide hotline.
The story, well the conceit, is that an ex gangster is brought back into the game by his boss to knock off his old friend who's in jail. So they smuggle him in and start to plan the hit. Meanwhile, his wife and daughter try to find out what has happened to him and deal with an army of hippies. Back at the jail the gangster accidentally takes acid and learns about peace and love. Not wanting to hit his friend he instead plans an escape. Everyone meets at the head mobster's yacht and everything ends happily.
Now that's a rather odd story but in true "Mad Libs" style, its when you pencil in the players that it becomes the incredible freak show that it is. Our hero gangster is none other than Jackie Gleason. His wife is Carol Channing. His boss is Groucho Marx, GROUCHO MARX. The person he's suppose to hit is Mickey Freekin' Rhooney. Is your mind blown yet? It's directed by Otto Preminger, the guy who also played Mr. Freeze in the Adam West Batman show.
Yeah. Now add hippies and musical numbers and LSD trips. Add Channing in "Mod" clothing and you'll either be puking or having nightmare for weeks. It's just an incredibly bad film, and I do believe the people behind it all were doing a little too much LSD themselves. There are just many points in the film where there is a set up and then.... NOTHING. It's like they forgot about it. Trust me, this is worth a watch, but for your own mental health do not see it under the influence of anything greater than popcorn!