An entertainer going into politics isn't inherently bad if they want to say or do something serious, but transitioning back just shows that politics is another branch of entertainment.

I have sorta felt this way about comedian pundits for a while but movie star -> politician -> movie star does feel more strange, not sure why, maybe because there’s more history of comedians doing political stuff.

Eh...I mean maybe, but what else is he supposed to do? He can't be President, there's only so far up the cursus honorum he can go, and he also does plenty of elder statesman political talking. He served as an elected official and then went back to his old job while still engaging with public life.