I just updated to the newest Ubuntu LTS, which puts pip into system managed mode so you can’t easily install packages outside of a virtual environment anymore.

If you (or anyone who stumbles upon this comment in the future) run into this problem, the new recommended way to install yt-dlp through pip and keep it in your path and up to date is via pipx (sudo apt install pipx). The syntax is a bit gnarly for pre-releases, so I figured I’d post an update:

To install the nightly: pipx install --pip-args '\--pre' yt-dlp

To update the nightly: pipx upgrade --pip-args '\--pre' yt-dlp

I alias the update command and run it before every download session.