Is it just me or do all these characters strive to be completely unlikable?
The show will make much more sense if you tier off the characters
Will McAvoy - The conception of how Aaron Sorkin sees himself now. Powerful, rich and successful and desirable to women and one of only a very few people to have the guts to "tell" the "truth"
Jim Harper - What Aaron Sorkin sees of himself when he was starting, before he became Will McAvoy.
Mac - What will happen to any woman who either hurt or spurned or did something wrong to Sorkin, in his eyes. That they will be a total mess, only completely infatuated with his memory, desperately wants him back and her whole life revolve around his approval/displeasure
Maggie - What a woman was and on the edge of what she could be, before she becomes a "Mac" to a "Sorkin" That she's some kind of nostalgia for the kind of idealism and certain innocence that Sorkin misses in his current exes. When Mac tells Jim that he should work for ACN, she points out Maggie and say, "She was me before I ended up as me now" Not sure how Sorkin could lay it out any plainer than that.
Don - What you get if you don't end up with Sorkin or cheat on Sorkin or leave Sorkin for someone else, you get a jerk and you get to see all his jerkish behavior and see him repeat the pattern over and over, no one of substance but someone who knows how to dig into a woman's weaknesses to keep them.
Every other character, esp the minorities, exist to have those five in the center of their world, all the time.
In real life, Aaron Sorkin, when he wasn't hoovering cocaine like an aardvark knocking over a kids ant farm, he was completely whipped by singer Kristin Chenoweth. He probably put her on the West Wing, where her lack of acting skill continued to shine through, and his arguments with her view of Christianity and politics and her subsequently leaving him just left him a broken shell of himself. In Studio 60, so much of the show was devoted to personal digs at Chenoweth through the characters, plus the odd pairing of sketch comedy and shoving politics in people's faces, that it killed the entire thing. At least with West Wing and Newsroom, there is an actual storyline context for Sorkin to shove his politics in your face.
Here's the problem with Sorkin
Pre busted for coke Sorkin along with pre Chenoweth Sorkin didn't try to create perfect people. He created people with perfect "intentions" who tried to do the right thing and sometimes they failed and sometimes they won, but ultimately they tried to do the right thing. The West Wing characters made a lot of mistakes, but they were honest mistakes and they were very human people and he had actors who could show a lot of that human quality ( esp Bradley Whitford)
Angry at the world Sorkin with a criminal record and with Chenoweth sucking off some other guy era Sorkin simply created "perfect" people in his own archetype. A young him and an older him. And all he cares about is his view and grinding an axe against any chick who he thinks wronged him. It's also why Jim and Will have women all over the show all over them. Esp egregious was Lisa Lambert complaining that Jim won't think she's "smart enough for him"
With West Wing, even if you didn't share Sorkin's politics, you could engage with the characters. They were three dimensional and very human and while they all spoke "Sorkinese", they all have a distinctive voice because he had a great producer, John Wells and one of the best TV directors in TV history, Thomas Schlamme. With Newsroom, if you don't share Sorkins politics, then the show runs pretty hollow, because the show is designed to prop up Sorkins views and belittles anyone who has a contrary view. He's also without Wells and Schlamme, and lost their talent in fleshing out true three dimensional characters. If Sorkin wrote West Wing like he does Newsroom, all Republicans would be hairy trolls who eat babies and set cities in fire using classic books as kindling while raping women.
I don't think Sorkin is a misogynist, however his seething wrath with Chenoweth is a little tired. You could even see a lot of it seeping to the surface with The Social Netwoork and Moneyball. (Scenes with Eisenberg and Rooney Mara and scenes with Pitt and his ex wife)
What Sorkin does have in his favor is a hit show in West Wing under his belt that carries with him a cult following, he works in a town where being a one sided liberal with anger issues and almost heavy handed condescension is totally ok and he writes a hell of a pilot episode. He knows exactly how to write one big scene per pilot that encapsulates what a lot of people feel and want to say, but don't or can't put into words. The problem is those big scenes are generally moderately toned while the rest of his shows tend to bleed antagonizing liberal all the rest of the way through.
Oh, and for those of you whom seem to care. The actress who plays Lisa Lambert, she used to be a cocktail waitress in a club in Southern California at one point. If you look hard and deep enough, you might find pictures of her as such.