Sondheim's sense of “in it but not of it” is not just a gay vantagepoint in 20th Century art, but a Jewish vantagepoint also. American Ashkenazi Jews of the mid-20th Century, the children or grandchildren of immigrants, were also involved in a struggle to assimilate into a culture that wasn’t theirs. And they often had a dramatic influence on that culture, creating much of what we imagine as American! But still, maybe because of that authorship, having a burdensome awareness of the artificiality of American culture. The arbitrariness of naturalness. So we see in his writing that deep Jewish longing to let go and belong, even while questioning the authenticity of the thing we want to belong to.