For example, he's got a great extended bit that he does on gay villains in movies that reveals how homophobia can be a lot more insidious and subtle then most straight folks realize.
The idea that gay people have, in the past, been presented almost exclusively as villains in the media was an eye opener for me. Yet that lesson is presented in a super funny way. I appreciate that whatever his agenda might be, James always leads with funny instead of seeming preachy. And though he's amazing at doing impressions and characters, he uses those skills to take people on a ride to challenging places instead of just using them to get cheap laughs.
Also, it's fascinating to watch how he talks about being gay. He does it in a straight-forward, honest, non-stereotypical way. He makes it seem like not a big deal and just another part of his act. It's just another subject to examine. It's like when Barack talks about race in that it feels like a step forward in the conversation.
Even the way he drop it in as a "no big deal" part of his act (usually about 10-20 minutes in) feels pretty radical compared to how many gay comics out themselves right from the start (or never come out). I imagine it's a bit of a tightrope walk and he deserves credit for pulling it off in a smart, funny way.
Related: A while back, I mentioned this...
There's a new crop of gay male comics coming up. Guys who talk about being gay but don't rely on the usual stereotypes about homosexuality to get laughs (e.g. Brent Sullivan, Gabe Liedman, etc.). There's a great feature article waiting to happen about that. Get on it New York Magazine.
Blackbook Magazine got on it with Will the Gay Comedians Please Stand Up?