I was highly amused when I found out his starting president was a Conservative named Steve Butt. Cue ass jokes and puns...
The random name generator can make some...interesting names. Fortunately they don't have any in-game impact, or having a Founder named Karl Buttman, or, worse, Dick Toogood (seriously) would make the game impossible to win.
I got Lacey Duvall as my starting lawyer girlfriend. I can't only hope it's that Lacey Duvall...
A good deal of the "enlightenment" quotes are hilarious, but "-Hostage- demands that -Interrogator- stop looking like Hitler." (gotten by giving the target hallucinogens and wearing an imposing outfit while they're still afraid of you) takes the cake.
When you take over the radio/cable news radio station to make your own program, there is a chance to make such a good show that the security was listening to/watching it instead of doing their job and waiting you at the exit. Doubles as a Awesome Moment.
You can intimidate Conservatives into backing away by yelling your slogan. Which can be anything from "We are the Liberal Angels of Death!" to "...", to "We need a slogan!".
Alex shouts the Liberal battlecry! Alex:We need a slogan! Police Officer gets out of there! Security Guard has a family!
If you have enough charisma, you can talk your way out of any encounter. Including the ones with guard dogs.