Ore, Twintail ni Narimasu., Binan Koukou Chikyuu Bouei-bu LOVE! Recommendations
Parodies of magical girl anime. OreTwi focuses on the power of twin-tails and using that to fight against giant creatures out to steal people's various attributes, be they of twin-tails, girlyboys, or glasses. And while most of the group is female, the main fighter is a guy who turns into a girl when he puts on his Tail Gear. Binan Koukou, on the other hand, is basically a magical boy anime that does nothing but make ridiculous fun of the entire magical girl genre, from the cute animal mascot to the monsters of the week to the transformation scenes - they're still guys, but dressed
Both of these anime are parodies of the magical girl genre. Binan is a magical boy show whereas Ore Twintails has a male MC that transforms into a magical girl. They both have..."creative" enemies that are generated for comedic appeal rather than intimidation. These two definitely fall under the "ridiculous and random" category of anime.