33. Kylie Jenner as Madonna (2019)
Kylie Jenner channelled her inner Madonna for Halloween 2019. The reality star recreated the singer’s outfit from the 2003 MTV Video Music Awards by donning a figure-hugging black outfit and pulling her blonde hair back into a low bun. The MTV Video Music Awards took place in 2003, but she nailed it.
She did this in an attempt to imitate the appearance of the singer. Anastasia Karanikolaou, her companion and friend, was also dressed up as Britney Spears while they were together. Anastasia was also dressed up as Britney Spears. They recreated the infamous kiss that took place between Madonna and Britney during the Video Music Awards and posted it on their Instagram Stories account.