Kristen Stewart
Jenny Lewis featured tons of famous leading ladies in her 2014 video "Just One of the Guys." Kristen Stewart dresses up as a dude alongside Anne Hathaway and Brie Larson. The shoot looked like a ton of fun.
Shia LaBeouf
Shia LaBeouf plays a version of Sia in her video for "Elastic Heart" opposite Maddie Ziegler. However, Sia faced some backlash considering Ziegler and LaBeouf have a major age difference. She apologized to viewers who were upset by the video and explained the two were meant to play versions of herself.