Making a TV show is a long process. A creator has to pitch it to a studio who has to sell it to a network who has to tell the creator it's now a reality dating contest who has to hire a lawyer to get the rights to his show back. It takes so much hard work from so many people that when it makes it to TV and it's still categorically insane, something rare and special has happened.
When I compiled this list, step one was disqualifying everything from Japan. They only make TV shows in Japan because they're trying to get rid of a surplus of adult diapers and Japanese people, and they're not subject to our interpretation of sanity. If they were, one person in the history of the world might have said, "I bet they don't really buy used panties from vending machines over there." Also, I eliminated every show that was intentionally strange. This should save you the trouble of typing your favorite silly cartoons in the comments section, or at least it would have if you weren't already there doing that. For everyone else who has made the brave decision to relax and enjoy jokes about crazy things, you can start now.
8Man vs. Beast (2003)
At first glance, this seems far more awesome than insane. Men fighting beasts is a great idea for a show. It's by far the best way for both things to die (in your face, cancer and bear cancer), and if you're not curious about who would win between a man and a beast, that's probably because you're more curious about who would win between a man and a dick tampon. I hear you talk a lot about how you're three times stronger than us, chimpanzees, but it's just a pile of fruity gym muscles if you don't back it up. I say we meet in a steel cage and the loser leaves Hominidae.
The first problem with the show is the obvious ethical issues. You can't beat up animals, even if it's sweet. An animal can't tell us if it wants to box or not, but I'm not sure why we care. I know enough about talking kangaroos to know that the first animal who can consent to a boxing match is going to be a fucking asshole.
The second problem with the show is that the only thing most animals know how to do on cue and with any enthusiasm is fight to the death or impregnate a surprised chicken. When you take those off the table you're left with a tug-of-war or maybe a race or something. The producers tried their best to come up with events, but the main reason most animals are sandwiches is because they suck at everything. Their competitions were things like a hot dog eating contest against a bear, an obstacle course race between a Navy SEAL and an ape, and 44 dwarves vs. an elephant in an airplane pulling showdown. Incidentally, if I had a show about men fighting animals and animal rights groups and uncooperative kangaroos ruined all my good ideas, 44 dwarves pulling an airplane against an elephant is exactly how I would tell everyone to screw themselves.
The producers had completely given up by the time they put an Olympic gymnast against an orangutan in a hanging-from-a-bar motionless challenge. It was about as compelling as watching someone die in a plastic bag against a goldfish. The contest went on for several boring minutes, and in an outcome too predictable to see coming, the ape wet its pants and lost interest. Humans! Humans! Humans! Honestly, I would have felt sadder for the orangutan if I was watching it lose a pistol duel.
7Bosom Buddies (1980)
Bosom Buddies was originally going to be an ordinary comedy about two single guys, but someone said something wrong during a pitch meeting. One of the producers claimed Billy Wilder as an influence and mentioned the film Some Like it Hot which got an ABC executive to suggest that it'd be hilarious if the men in the show were dressed as women. In a perfect world, you'd expect the other ABC executives to say, "Sorry about that guy-- he suggested the same thing in our meeting with $10,000 Pyramid and the NHL." We don't live in a perfect world, so the other executives said, "Ha ha ha ha! Dresses!? And men!? Sold!"
Now the show had to find a reason for the main characters to be in drag every episode. Their characters moved into a women-only hotel by disguising themselves as women. You know your show's premise is good when rapists hear it and gasp, "Oh my god, that's genius." The show was cancelled after two seasons because the only thing more ridiculous than wearing a dress to trick your landlord is doing it for a third year. Plus, Tom Hanks and Peter Scolari's woman costumes were about as believable as two men in wigs making no effort to disguise their voices. They lived in a world where everyone was so easy to trick, there was no need for the elaborate scheme. They might as well have put a jar of mayonnaise on roller skates and shoved it into the manager's office shouting, "That's not male mayonnaise! Rent her an apartment! Actually, rarg! I'm God! Rent an apartment to Tom Hanks and Peter Scolari!"