This is a perfect example of the dividing line between sharing Matt's sense of humor and finding him insufferable. For me it just gets more and more funny the more he repeats the line as it shifts from being a silly demonstration of repping a corner to becoming a full on commitment to absurdity. At the same time I can understand people who watch Matt's character in The Dirties and even NTBTS and just feel the way Owen feels throughout this film, "oh my God enough already." Matt himself shows excellent awareness of this fact by providing a straight man proxy (Owen, Jay, etc) for his character to orbit around but also tether itself to when it's time to reel things in.