Hill certainly does more than he did in Moneyball which begins right with his creation of Donnie. He plays the part with a somewhat course voice in attempt to play a certain kind of businessman of the period. It almost seems like he is trying to play the part as perhaps Joe Pesci would have if the film had been made exactly when it occurred. Now I could see Joe Pesci in this part easily and he probably would have been absolutely brilliant. Well Jonah Hill is no Joe Pesci, and Jonah Hill attempting to be Joe Pesci does not come anything close to Joe Pesci, that does not mean he is bad though. Hill wears the accent well enough and he does get into his character, and does become part of tapestry of debauchery as he should.
Donnie Azoff basically seems to be the worst of the worst among their group of men who decide to try about everything they can with the money they have. The story of Donnie is mainly being as disgusting as possible without a bit of shame in it. Whether it is using prostitutes, taking loads of drugs, or eating the fish of a poor guy of a guy who wasn't focused enough, he does it without blinking an eye, well unless of course the drugs make it hard to keep one's eye open. Hill again does well enough in these scenes as he does throw himself into them with a great energy, and properly conveys just how much joy Donnie gets from his own antics. Hill's portrayal of these antics though are just not ever nearly as memorable as Leonard DiCaprio's portrayal, although the reason for that is for another time.
There is a little bit more to old Donnie than just when he ingests into his body though. There are scenes of Azoff actually doing the job of trying to make money. Hill is pretty good at being the obnoxious hustler, and does the purposefully overdone salesman speak correctly. He's of course very annoying, but I will grant him that is the point of his character. There is a little more though when Donnie comes down a little from the various substances he is abusing, and stops abusing other people. The businessman in a rather precarious position is well handled as he tones down Donnie in the right way. This bringing the appropriate nuance within the near "monster" of a strange sort that we see in the general comedic portrayal.
There are a few questions that need to be answered in regard to this performance. Does it make it less egregious that Jonah Hill has more Oscar nominations than Toshiro Mifune, Donald Sutherland, Richard Attenborough (in acting), Guy Pearce, Ewan McGregor, and Brendan Gleeson combined? The answer is no. Is he the best supporting actor in the film? No once again, certainly not over Matthew McConaughey's brilliant almost one scene wonder or Jean Dujardin or Kyle Chandler. Is he consistently overshadowed by Leonardo DiCaprio's performance and Martin Scorsese's direction? The answer is yes. Could someone else have been better in the role? Yes. Is it a more than decent performance with good enough moments? I would say yes to that too.