I'm assuming could be a visual/display problem in that embedded video playback/player plugin, etc. requires UI to properly function and headless mode puts it in a weird state. Video is different from static images and animated GIFs in the technology used to render the content.
Would be interesting to see if headless Firefox has the same issue or not. Alternatively, you could also try running the test in a headless setup that's not docker based. Could be docker related as well.
If you've narrowed it down to Chrome (docker or not), perhaps you could then bring this up with the Chrome/ChromeDriver team as it wouldn't be Selenium specific.