Although it is impotence that initially drives Portnoy to Doctor Spielvogel, his underlying complaint is not overtly sexual in nature: he contends that the very fact of his Jewishness is responsible for the degradation and shame that has cripples him emotionally and even manifests physically.

Outside of this more personal context, however, is the broader concern with the oppressed state of the Jewish people, particularly in America. While he harshly tears down what he sees as the Jewish tendency toward self-hatred and isolationism, he simultaneously acts as a proud Jewish man. His attitude towards gentiles is similarly conflicted: while often idealizes them internally, he shuns them outwardly. In short, this conflicted attitude towards his Judaism pesters Alex so much that it becomes the overarching theme in his sense of despair. Indeed, Judaism proves to be a theme more important his issues with his mother or his sense of guilt.

The oppressive weight of his Jewish heritage bears down on Alex and is the source of his constant sense of feeling stifled and lacking freedom. This notion of freedom applies to both his ability to act as he pleases and also includes a freedom from resentment, and the feeling that he could be different, less inhibited, if only he had been raised in a different cultural context—namely, in the home of calm, non-melodramatic gentiles. Those gentiles that embody this idealized way of life he imagines all gentiles to lead is typified by the families of the Pumpkin and the Pilgrim. He laments to Spielvogel, “this is my life, my only life, and I’m living in the middle of a Jewish joke! I am the son in the Jewish joke—only it ain’t no joke! Please, who crippled us like this? Who made us so morbid and hysterical and weak?" (36). The implication of this desperate rhetorical question Alex asks about being Jewish refers not only to his own life and how being Jewish has an effect on his behavior (and emotional health, for that matter) but how this applies in a much larger cultural sense. For instance, when Alex talks about the “Jewish joke" and asks who brought about the crippling effects, the “us" he refers to is an entire race of people, perhaps even outside of the context of attempts at American assimilation. He sees the entire Jewish state of being as one entangled in a tragic and depressing cycle of self-loathing and the fact that he is unable, in his mind at least, to escape it is a source of unending frustration to him. What Alex terms the “ridiculous disproportion of guilt" (273) that makes him want to scream, he is not simply talking about the guilt produced by his relationship with his mother or over his deviant or excessive sexual desires, this guilt is broad and applies to a culture rather than simply himself as an individual.

Through a series of rhetorical questions, Portnoy positions his reader as a Jewish man. His questions are addressed to a wider audience than simply Spielvogel; they are being addressed to an entire generation of assimilated Jewish males that might have been a contemporary of Alex’s, at least in theory. When he asks what is it “with these Jewish parents" and declares that he knows he is “not in this boat alone" he is posing this complex question to an invisible audience of Jewish men like himself and seems to assume they do exist and are agreeing, if not sympathizing with him. In this question regarding Jewish parents, he addresses not simply his doctor, but an entire subset of young Jewish men when he continues with the question, using the “we are" in the context of this large cultural and ethnic group “moaning and groaning with such pity for ourselves, the sad watery-eyed sons of Jewish parents, sick to the gills from rolling through these heavy seas of guilt—I can match you, you bastard, humiliation for humiliation" (118). Moments such as these are prevalent in the text and cause the reader to almost forgot for a moment that the character of Alex is speaking to one person, especially since he invokes so many complex, loaded questions that are not only rhetorical in nature, but are best answered the invisible but omnipresent audience of Jewish men suffering the same issues as a result of cultural, ethnic, and familial traditions and values.

As a teenager, Portnoy begins to question not only what he sees as the limiting scope of religious dogma and the negativity he feels it perpetuates, but the cultural and social implications of being Jewish, Alex is consumed with anger of the sense of repression his family, and the greater “family" of other Jewish people around him encourages and perpetuates. His father is chronically constipated and his mother is the single most castrating female figure in the text as she alternates between smothering him with love and its expression as burdensome guilt disguised as concern and degrading chastisement and this is not only a distinctly claustrophobic and tense environment at home, it also reflect the tension in the cultural and religious community Alex resides in. In response to this build-up of internal pressure, Alex tells his father that he “would rather be a Communist in Russia than a Jew in synagogue any day" and again, this is, in part, because the community of Jewish people Alex lives within is stifling and, in his mind, perpetuating the same negativity that he seeks so desperately to absolve himself of. In continuing this statement to his father, Alex goes on to say that they should not cry for him, since he has turned his back “on the sage of his people, weep for your own pathetic selves, why don’t you, sucking and sucking on that sour grape of a religion! Jew Jew Jew Jew.. It’s coming out of my ears already, the saga of the suffering Jews" (76). Again, the dominant theme in his frustrations that are distinctly cultural and community-related in nature are that of an inescapable sense of entrapment in a sad history with little possibility of breaking the cycle. Alex sees self-pity as one of the most deplorable aspects of the faith community, yet interestingly, he is one of the most experienced characters expressing constant self-pity.

The broader cultural criticisms about being a Jewish male that are expressed through the character of Portnoy typify the struggle between becoming a fully assimilated American man while still clinging to many of the aspects of his Jewish heritage and culture. These wider criticisms of the “plight of the Jewish male" he expresses are further complicated by paradoxes between his simultaneous desire to both become a gentile and to push away such a notion. Because of his upbringing and the guilt that still plagues him as an adult, Alex is unable to completely feel at ease when he is not in the presence of what he comfortable with culturally (i.e. being around gentile women) and bemoans his Jewish status. On the other hand, there times when he takes great pride in his status as Jewish man, if not only out of a communal sense of distress and defeat. One of the times he is proud to be Jewish in an “us versus them" kind of way is exemplified by his association with high school football. At one point, he victoriously states, “We were Jews—and we were superior! ….The outrage and disgust inspired in my parents by the gentiles, was beginning to make some sense: the goyim pretended to be something special, while we were actually their moral superiors. And what made us superior was precisely the hared and the disrespect they lavished so willingly upon us! (56). In other words, by being untied in defeat, comfort is garnered, which allows Alex to feel, for once, a sense of appreciation for a heritage he so openly claims to despise.

Portnoy blames a string of failed romances on the very fact of his being Jewish and creates situations in which he can at once experience life as a gentile (something he desires and is repulsed by, to radical extremes) through his interactions with women. Despite this, once he is bored with the mannerisms of gentile women, such as the Pumpkin and Pilgrim in particular, he simply takes the escape route of saying there are too many cultural differences for the relationship to move. The love and hate struggle with his status as a “Jewish boy" culminates in his tumultuous relationship with the Monkey, who at once feeds his need to experience the kind of abandon he feels gentile men are raised to partake in and is intensely jealous of, while at the same time enables him to persist in the negative cycle of self-loathing. Through his relationships with gentile women, his most intense struggles with being a Jewish male rise to the surface, and this makes him a volatile partner. He is wildly moody and prone to aggressive acts of self-hatred in the name of shedding inhibitions and being free, even though such actions only create more misery and confusion for him than happiness. These paradoxes form part of who he is and imply the inescapability of culture and heritage for him personally and in a representative sense, all of Jewish males in his situation.

Portnoy, while expressing the occasional sense of pride in being a Jewish man, is a conflicted individual because of the dual cultures he attempts to internalize. While on the one hand, his mother’s presence nearly crippled with him guilt and shame, this is a sensation he is oddly comfortable with and even if it repulses him, he is unable to find a suitable replacement in gentile women. Through his relationships with gentile women, his most buried instincts to find cultural assimilation in their arms is both a frustrated and doomed effort. His impotence serves as a physical manifestation of this frustration which ultimately, is the result of being raised as a Jewish boy in a household with particularly cemented Jewish norms.

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