I think you're right that the stand-up routine was supposed to be interesting. It was supposed to be cutting-edge. And, because Sorkin is being more patronizing than his usual self in this show, above the audience's heads. Did the show hire any actual comedy writers? They should.

By the way, I have done stand-up. In 5th grade. For my school's talent show. I stole Gabe Kaplan jokes and wore bright suspenders, like Mork. I killed 'em.