Yes, there's definitely a "line" in comedy. It's all in how you construct the joke and how you address the subject. Jim Jefferies has done a pretty good job, albeit lower key, of transitioning his comedy and showcasing how the line moves.
This is one of my favorite Burr pieces, but it certainly wouldn't pass muster today simply because he used the F-word. Forget that the subject is toxic masculinity and engrained homophobia.
As for Rogan, I believe he should be more responsible with his discourse and how he handles his guests given his reach and influence, but ultimately it is up to the consumer to digest his content critically.