I think that one is a bit risky. For one thing, they casually roast themselves pretty frequently. For two, they've got quite a lot of baggage that they might not enjoy other people opening back up. And nothing ruins a fun roast like somebody taking it too far and making it too real.
Having the comment about things going over your head, proceeding over your head is good stuff. On purpose? Doubt it. Benefit? Ill give it to him this time. #rambleriscringe