I don't have a lot of T-Shirts anymore, but my favourite is probably one from a youth club in eastern Germany with Boss "MyName" (but the wrong spelling) on the back, and the logo of my late father's long bankrupt company as a sponsor on the front.
It's funny, but more in a nostalgic way.
It sounds like you don't necessarily like the idea of using a container (I tend to use podman, but most guides are for docker, so that'd probably be easier for you). From my experience, containerising things actually makes things a lot easier, especially in the long run, and getting started is a lot easier than it seems. You can probably find a ready-made guide to set up a plex or jellyfin container on Debian.