There’s really only one interesting question when it comes to Oprah Winfrey, whose record of accomplishment is so extraordinary and whose past is so morally unblemished that even Kitty Kelley, perhaps our nation’s most resourceful scandal-mongering biographer, was forced to admit to the Washington Post, a few months into researching her biography of Winfrey, that the book is shaping up to be about “hope and promise and courage—I think those are virtues that Oprah believes in strongly and encourages her audiences to believe in.”

The Oprah Question is this: Can her narcissism—the profoundly self-glorifying way in which she conducts her life—undermine, taint or compromise the undeniably huge amounts of good that she does in order to further glorify and justify herself?

I take as a given two things about Oprah. The first is that she’s done a lot of good. She’s given away oodles of money, brought needed attention to various issues and causes (e.g. AIDS, sexual abuse of children, the plight of Katrina victims), made a lot of viewers feel understood and sympathized with, made American culture more accepting of black women, and helped Gayle King pay her mortgage every month.

The second is that there’s something missing at the core of her— that it’s true, as George Orwell wrote in his essay on Gandhi, that “Saints should always be judged guilty until they are proved innocent”?—and that the absence of an authentic and stable self inflects, or perhaps infects, almost everything she does in her life. It’s why we have Dr. Phil (who actually I don’t mind that much, but still). It’s why she’s become an advocate for The Secret, that self-help book that promises people the same bogus utopian paradigm that every other self-help book in the history of self-help-ed-ness has sold people. It’s evident in the obsessive control she exerts over her company, her image, and her privacy. And it’s evident in the way that, through selective and edited disclosure, she transforms even her weaknesses and potential vulnerabilities into further examples of her rectitude (e.g. her weight fluctuations, which should be evidence of a deep insecurity about her looks but have instead become a way that, y’know, she’s just like you and me).

The problematicity of Oprah was perhaps most painfully unavoidable in the recent speech she gave at the ribbon-cutting ceremony at that school for the Oprah Winfrey Leadership Academy for Girls that she envisioned, funded and, I’m pretty sure, put up the drywall for. She said:

I wanted to give this opportunity to girls who had a light so bright that not even poverty could dim that light. ?I was a poor girl who grew up with my grandmother, like so many of these girls, with no water and electricity.

This is Winfrey at her purest. Doing good, doing it brilliantly and thoroughly (we have no doubt that the Oprah Winfrey School for Wonderful, Amazing Girls Who Remind Me of Me will be well-maintained and managed). And doing it all, we’re forced to conclude, in order to remind the world, once again, that she’s a good person, a person worth caring about, a person deserving of success and love and admiration. Out of such qualities is both greatness and despair built, as Lee Siegel reminds us in his fascinating, if disturbingly narcissistic in its own right, essay on the Oprah Question.

The name Oprah gave to her production company–her business–is Harpo Productions, which is "Oprah" spelled backward. That is exactly right. Winfreyism is the expression of an immensely reassuring and inspiring message that has, without doubt, helped millions of people carry on with their lives. And it is also an empty, cynical, icily selfish outlook on life that undercuts its own positive energy at every turn. On her way to Auschwitz, sitting in her hotel room in Krakow, thinking about the masses of people who were murdered in the death camp, Oprah wrote in O, "I have never felt more human." Her empathy and moral growth seem to require human sacrifice. Yet watching Oprah does fill you with hope. It also plunges you into despair. She has become something like America itself.

The Oprah Question is not, as it often presents itself, whether we can tolerate Dr. Phil and The Secret and James Frey crying on television for the sake of the many people Winfrey’s helped. We can. The Question is whether there’s a genuine psycho-political analogue to the pop psychological power-of-positive-thinking, if-you-feel-it-it-must-be-true theories which Winfrey has so persuasively sold to the American masses. The Question is: Can a society, like a person, only truly progress if its icons and guiding philosophies are psychologically healthy? Can someone like Winfrey truly make us better when she herself is so obviously dysfunctional? Must health and goodness be the wellspring of social progress, or can history, with all the tricksyness at its disposal, make lemonade out narcissistic lemons?

Tough call.