Sounds like you want to stay in the comedy-action-horror triangle, maybe with a little bit of room for a thriller. I wouldn't overthink it.
If everyone liked Rear Window try Under the Silver Lake. Male loneliness + Hollywood exploitation + Billionaire conspiracy. The movie itself has hidden messages and codes in it. Nothing subtly communist though. More like 70s paranoia but for today.
The Blob (1988) is supposed to be a nice inversion of the original, and counter to cold war sentiments of the time. I can't vouch because I have yet to watch it.
Enemy of the State, classic 90s Will Smith and Gene Hackman being an unofficial older version of his character in The Conversation. It has a faster pace and a bit more action than The Conversation. It got a jump on the post-9/11 surveillance state stuff.
None of these are particularly communist. However they might incept your friends with the idea that the government and elites are corrupt and dangerous.
His people spent all morning going on the Sunday news shows, telling everyone this isn't a war and everything is complete. Then he just drops "You know what? Why shouldn't we coup Iran?"