Barbra Streisand
Streisand was one of the original divas. Before she arrives at venues (well, used to) she asks the township to sweep the venue with police dogs. She also requires all of her crew and the employees of the venue to dress "nicely" (no t-shirts or jeans). Seriously, she was that bratty.
One Direction
The now-defunct boy band that ran the circuit in the early 2010s made some fun requests in their day. On their 2015 tour, they requested that each venue be stocked with beer, KFC, a ping-pong table, and soft toilet paper. Compared to what other celebrities wanted, these guys made it easy.