Done kindly, this sort of thing isn't just funny but an insulator against actual silencing. (I can't speak to how the Stalin photo was meant, but it sure could be funny.)

If someone is outraged by your support for social programs and calls you a Stalinist, it's way harder to feel threatened when you're looking at a framed photo of Stalin your boss gave to you. Similarly libertarianism/Somalia or whatever other over-the-top pairing applies. It's part of why I tend to defend this sort of humor as not inherently wrong - when it's well-meant it helps ensure that people don't feel threatened or ostracized. The sting has been taken out of the attack, so there's more room to get along.