Where: George Michael's "Freedom" music video

When: 1990

This is the music video of all music videos, at least in terms of model cameos. Naomi Campbell, Linda Evangelista, Christy Turlington, Cindy Crawford, and Tathana Patitz all make an appearance in the video for one of George Michael's hits—that lucky guy! The only model missing from this pack is 90s supermodel Kate Moss. Still, the visuals achieves some sort of holy grail status.