Marilyn Manson
Manson historically just did everything to shock people. He never asked for too much, but he always wanted gummy worms, Doritos, a Manwich, microwave popcorn, and 2% milk. All of this was performative, and he usually left most of the food he requested behind.
Madonna
Madonna had, quite possibly, the most wholesomely insane request of all time. She requested a 200-person entourage to escort her into her show. Additionally, she wanted her dressing room to exactly resemble her own personal home. Yeah, that's pretty silly.