Yeah this is kinda a point. People like this colleague seem to have gotten stuck in a highschool bully mindset ans never moved on. All of their jokes are about people who are different, their whole status seems to be based on their "masculinity". In my experience this is the largest portion of homo/transphobes here in the Netherlands. People who aren't violent or outright hateful, but rather just pushing outdated jokes and viewpoints and then getting annoyed by all the "woke bullshit" when they get called out.

My tactic so far is to not fully attack back, but rather staying friendly while showing my disappointment with this behaviour unless it goes too far. Most of these people are otherwise decent, and in my opinion may be swayed by someone "woke" who doesn't go "full crazy sjw" but does call them out. Making a joke about minorities is way easier of you don't know anyone well from those groups. They're not crazy Trump voters, so they may still be steered in the right direction