Was bumping Without Me a minute ago and the thought of "Eminem will never make a Guess Who's Back type of single again" make me somehow sad. Ok, the man is almost 42, but I think he could still pull it off a funny single without seeming forced.
Look at MMLP2. The 'tongue-in-cheekness' is there on Brainless, Asshole (just two examples). So I think that with a catchy beat (Dre, Eminem, anyone), Em could make a funny single without seeming weird. I wouldn't look at him like "Oh, man, he is too old for this shit, because, like I said, look at MMLP, look at Calm Down, look at Twerk Dat Pop That. He could easily do a guess who's back type of single perfectly.
Thread was made because of that line in Guts Over Fear too.