Roleplaying has always been weird. I cannot refute this simple fact, nor come up with an apology for it on why it isn't weird.
For the case of fanfiction, I think it has to be written very well in order for it to not be 'cringe.' As well if you want to do a funny fanfiction, you have to read and imitate postmodern comedy works as this is now considered the epitome of comedy.
Drawing funny works is very simple to do also, and yet, when someone does a very detailed funny fanart, it often gets criticized as tryhard, or so.