Michael J. Fox in Back to the Future Part II (1989)
This list can’t be all serious like I mentioned before. So, here’s an example of a rather comical cross-gender role. And I gotta admit, I completely forgot that Michael J. Fox played a woman in this sequel of the 80s cult classic. In the sequel, Fox plays a number of characters, including Marty McFly, Marty Jr. and, Marlene McFly (Marty McFly’s daughter).
Source: brightside.me
And let’s all admit that he played a pretty good-looking daughter, too. The movie came out in 1989, which was only two years before he was diagnosed with Parkinson’s in 1991. Fox kept it a secret from the public until 1998. Then, as you know, he became an advocate for finding a cure. He founded the Michael J. Fox Foundation in 2000.