Quote:
If hes your friend, take him aside and cut it out.
Second, although not the "best" way the following a funny and effective way to do it:
Absurdity what ever he says.
him: hey everyone, doesn't his pants look like something a homeless man would wear!!!
*everyone laughs*
you: haha, oh man...how did ya know?!? I beat up a homeless man a few hours ago and stole his pants cause they were so sexy! (this is said is a very fun and playful way)
Another good way is to straw man him:
"Oh man, dude that was funny! I bet you cna tell another joke that will make us laugh like CRAZY! Like right now..."
Again, this has to be said in a fun and playful way so not to sound like you got offended. Basically this sets him up to an impossible standard of comedic ability, of which he wont meet.
You can use the straw man stuff in a bunch of ways, be creative.
I totally forgot about this, homie! I dig the first way you posted. He'll blurt out some stupid shit like, "This my friend Nick. He has a small penis!" "hahahahha" But Nick, you gotta respond back like, "It's not about the size, it's the motion in the ocean". BEAST!!!
We gonna drop his cock blocks this weekend. #AntiCockBlockSwag