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.