Why am I still thinking about this? Because that nagging sense of having been dissed by proxy by Huey Lewis's Billy Flynn portrayal in Chicago didn't go away, and in thinking about it I decided it was probably somewhat connected to the anger issue I noted before. The comment I made earlier, "detracts from the command Flynn would naturally have as a lawyer," is at the crux of it. Basically, I think Huey slightly misinterprets Flynn (assuming he wasn't explicitly instructed to play him exactly this way), portraying him too much as just being in it for the money, when in reality the money's just a byproduct; Flynn's really in it for the esteem he gets as a lawyer.
In one scene, for instance, we see Roxy's husband Amos encounter Flynn and try to stall for time because he only has raised $2000 of the $5000 Flynn requires for his fee. Amos is a meek pushover of a guy, an impotent combination of naivety and spinelessness. He's no match for someone debonair and sophisticated like Flynn, and the play really drives home that contrast with many of the musical numbers (compare Flynn's "All I Care About is Love," where he sings about loving the attention he gets, and Amos's "Mr. Cellophane," which laments how no one ever even notices him). So when this confrontation happens, we know that Flynn is going to end up with what he wants: the case itself and the attention it brings, on his terms. There's no way Amos could stand up to Flynn to arrange for things to be any other way.
When Amos doesn't have all the money like he's supposed to, Huey's Flynn really lets him have it, practically threatening to drop the case right then and there. In my current state as an aspiring almost-lawyer this scene bothered me because it makes Flynn seem like a petty mobster, a bully, practically shaking down his clients for exorbitant sums in order to continue representation. Lawyers may be criticized for many things, but overt extortion is generally not one of them (though naturally there are exceptions). (And lawyers may withdraw if their clients cannot pay, but usually not so unilaterally as to prejudice the client.) Lawyers may, of course, be thought of as smug and smarmy (qualities Billy Flynn has in spades) and heavily resented for it, but that's because lawyers are regarded as authorities, and people resent feeling dependent on them. A lawyer who plays up the inherent power their authority gets them is more likely to be seen as slick and oily, but exploiting that position of power is not the same as engaging in outright wrongful behavior. The problem with Huey's Flynn is that he has him doing the latter and not so much the former. Which not only made me squirm, but also seems contrary to the way the role is scripted.
Billy Flynn clearly loves the attention he gets from his authority. He sings about it. He speaks about it. It's his motivating force. So when Huey has him get actually angry with Amos, he's abdicating the natural authority of his character. Which is particularly jarring in this context, as Amos is the kind of guy who would show deference to a telephone pole. That exchange between him and Flynn should really be about Flynn toying with him like a cat toys with a mouse. It should be false-anger that Flynn projects, enough to remind Amos who's boss, but not in a way that communicates animus. Huey could probably play the argument sarcastically, comedically, maybe even winking at the audience as he lets Amos walk off dejectedly before reeling him back. We all know that Amos will take him seriously and do what he wants, so there's no need for Flynn to actually be serious in the argument. But the way Huey plays him, he is, and as a result his Flynn almost seems desperate, pretty much relenting at the end of the scene in order to keep the case. Which doesn't make sense, because someone like Flynn would have been in control of the whole situation, and certainly no insignificant spec like Amos should have been able to wrest it from him.
Especially because there's a later point in the play where Flynn is engaged in a genuine power struggle, when Roxy challenges him. Unlike Amos she is not an insignificant spec, and it seems like the two argument scenes are designed to stand out in contrast with each other (diminishing Amos's character earlier helps promote the strength of Roxy's later). When Roxy doesn't abide by his instructions, when she asserts herself as being more important than he is, that's genuine anger that comes out of Billy Flynn, because she's truly questioning his role as an authority and weakening his control of the situation. For someone like Flynn who does what he does for the near reverence he receives as a result, to have her undermine his position would be genuinely threatening. So when he argues with her, that should be real anger, defensive anger, because he has a lot to protect with it. (Meanwhile if he were only in it for the money, there would be little reason to argue at all since he'll get paid no matter what happens at trial.)
Anyway, if this all seems like a bit too much attention to be giving to one play, well, it is. Except in as much that I often think about how people interact and relate to me differently as I go through this Great Change and incrementally become more and more a lawyer. I do see differences in the esteem people treat me with. I see also that it's my choice to decide how to respond to it, and the different consequences those choices have. So it's something I'm attuned to reflecting upon, and when I saw the play I couldn't help but do.