On MacOS 10.15.7 with Plexamp 3.3.1 my media keys no longer work at all. Plexamp is the only media app open (and I’ve even tested closing everything else too) so I don’t think something else stole the keys. I’ve tried quitting and reopening, still nothing. Even if I click in the app (say mouse click on pause), I cannot continue by hitting pause/play. I have tried both with my USB keyboard as well as the touchbar. Any ideas?
Go into the plexamp preferences and check if there are any keybindings defined at all.
Big Sur here. My keyboard media keys are all working, as long as Plexamp was the last media player I interacted with. Play/Pause, Prev, Next.
You tested closing everything else? Chrome likes stealing media controls.
FWIW I don’t have any Global Keyboard Shortcuts defined within Plexamp.

That’s the default. You need to define them first.
This was done to steer clear of conflicting global shortcuts of other apps, which have been reported by some users.
Right.
Without anything defined in Plexamp, the dedicated keyboard Prev, Play/Pause, and Next buttons are working fine for me.
The dedicated keys are kinda special. macOS automatically sends them to whichever program used media last. You can’t type them or redefine them, usually.
If I define other Global Keyboard Shortcuts within Plexamp, those also work. That’s actually nice, because they always control Plexamp, instead of how macOS controls which app gets the media keys at any time.
My guess is that - as @soehlert was hinting - something else on his system has hijacked the media keys. It’s super common.
Edit:
@soehlert - when you press Play/Pause, does Music.app open? That ordinarily launches if nothing else is registered to use the media keys. Try rebooting.
Then check in System Preferences -> Security & Privacy -> Privacy -> Accessibility. Is Plexamp listed there, and does it have a checkbox? Back in Mojave this was necessary. I’m not sure if Catalina still needed it.
Yes I literally only had Plexamp open. Nothing else to steal my keys. I even quit Plexamp last and reopened it as the only app open and still nothing.
I checked the accessibility thing and it was still on. I have prevented my Music.app from ever responding to the media keys so no it does not open that.
I’m not entirely sure why this just fixed it, but I went into Global Shortcuts and tried to set the previous/next/play|pause shortcuts as the media keys on my keyboard. It didn’t accept the shortcuts, but now the media keys work? That kinda makes me think Plexamp was accepting the keys but doing the wrong thing with them. Either way it’s fixed now.
Yay!
What do you mean - how have you done that?
You have to disable SIP, make some changes (move the app, remove the app, chmod -x it, or something along those lines), then reenable SIP. Now iTunes can’t open at all.
Ahahahah that’s certainly a nuclear option!
(Media keys are mapped by default.)
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