Middle finger is fine to have if you need it. Jonny said PG 13 rules and gave movies as an example. I think you can make 1 video each but i don't know if you can submit 2 videos. you could probably post both on youtube (if you have a channel) or as a devlog on itch, but submissions probably have only one video submission spot.
Viewing post in questions on what is allowed
I don't know enough about the jam submission to answer that, but I think if you ask this question on the discord page you will probably get a better answer. I can say that if you are submitting 2 games, then yes 2 videos should be fine, but with just one game the game jam submission only has room for one url, so you cannot upload 2 videos in one submission.