When a young person leaves college, she is subjected to a unique conflagration of pressures and expectations regarding her place in the adult world. Secondary education inculcates a sense of the world as an inherent meritocracy, rich with wealth and opportunities for those few, select souls who are willing to trade sweat and sleep for the ability to contribute meaningfully to the project of Western Civilization. This is a lie. The point of contemporary liberal arts education is to produce graduates who reinforce the value systems inherent in liberal arts education. It is a closed system, having little or no awareness of the extraordinary gaps which exist between students' ideas about the nature of the work that they think they desire, and the modern realities of industry. The net result is that one privileged subclass of the awakening generation, those able to survive the financial and temporal burdens of higher education, is destined to face a unique kind of heartbreak in its third decade of life. For most of its members, the work that they find themselves doing (assuming they find work at all) will neither align with their expectations, nor resemble the work they have been doing to qualify themselves for a degree, nor produce any of the expected feelings of belonging and contribution that had been held out as the carrot at the end of their education. Just prior to the 2008 worldwide financial meltdown, two films were released which examined many of these themes through the eyes of intelligent young women whose shock and dismay in the face of modernity's revealed horrors echoes not only many of our own early adult disillusionments, but also captured in metaphor the brewing resentments which would underpin the class and gender wars that would subsequently characterize Western culture in the 21st century. The Devil Wears Prada was released in 2006 to a box office reception of $326 million against a $35 million budget. Regardless of what the film was intended to be about, we think of this as "the Meryl Streep dragon lady movie," and for good reason. The role of Miranda Priestly is exquisitely written, and Streep's performance is about 300% more nuanced and smoldering than any other actor would have had the guts to attempt. But the performance in what is essentially a large supporting role is such a tour-de-force that it eclipses the story trying to be told about Ann Hathaway's journey from the ego-bolstering confines of a liberal arts career path, through the cold water bath of the actual job market, and out the other side into a Hollywood-improbable clear-eyed view of her place in the world. Andy (Hathaway) wants to be a journalist but shockingly finds she cannot find a way to be paid to write immediately after college. Through a kata of rationalization-jitsu, of which all twentysomethings are masters, she decides that a year spent as an executive assistant to the editor-in-chief of a fashion magazine will buy her just enough experience to at least find the first rung of the career ladder she wants to climb. The initial conflict comes when Andy is ambushed by the cultural norms and requirements of this new bizarre workplace. Both Andy and her unshaven boyfriend (Adrian Grenier) verbally espouse the liberal arts iconoclastic party line, seeing the world of fashion as an amoral drain on the world's artistic resources, an industry belonging to the shallow, the privileged, and the intellectually inferior. The main conflict arises from Andy's growing realization about the hidden complexities of not just the fashion industry but the very nature of adult work itself. It is not incumbent upon any job to conform to some Richard Scarry simplistic ideal, and to leave your college's job fair expecting this is both a prescription for heartache as well as one of the great tragic inevitabilities of the modern age. No, the "purpose" of work (if such an "intentional" word can be used for such a thing) is to provide the worker with a path to self-expression and realization through the societal use of (sometimes arbitrary and artificial) obstacles and constraints. Andy's mistake, and her tweed-monster of a father's mistake, is in hyperfocusing on any given avenue of achievement, chosen without the benefit of experience nor any associated humility, as the "solution" to some grand riddle handed down from the Sphinx of the Middle Class Lifestyle. The emotional torment experienced by Andy is not because "misfortune" has cast her into the path of some malevolent boss-zilla, but rather because as she rises to the challenge of her job, she actually feels satisfaction, which flies in the face of everything that she has been taught about how the only way to be happy is to follow your bliss, lean into the brass ring, and eat and pray and love. She finds it impossible to do any of these things, and still somehow is surviving and thriving. The Nanny Diaries, starring Black Widow, Captain America, and the Truman Show lady, which made $48 million on a $20 million budget. At the time of its release, the Dow Jones Industrial Average still stood in the mid-13,000s, and we were thirteen months away from the September Crash, the steep downward curve laying ahead of us unseen. A film about the difference between rich people and poor people was ripe and timely; we just didn't know it yet. Scarlett Johansson plays a befuddledly intelligent college graduate who despite being friends with Alicia Keys has no discernible direction, drive, or talent, until someone improbably mishears her name "Annie" as "a nanny," which somehow leads immediately to a highly paid live-in childcare position in Manhattan. The story is narrated by Annie herself, told in the form of an anthropological field diary, presented as a case study in the behaviors and patterns of this bizarre civilization called "the wealthy." This framing device, an older and wiser Annie looking back on the lunacy of her first job out of college with a scientist's objective eye, foreshadows Annie's eventual disillusionment with the value systems with which she left college. It turns out that wealth neither ensures a life of ease nor corrupts absolutely, but rather interacts with its holder according to a complex matrix of character and circumstance to produce an empirical result that is still open to interpretation. What appears to be success or failure in career and family often in fact contains a spectrum of positive and negative forces, which in any given moment may seem to resolve into a certain moral "shape," before new waves of forces and evidence require the observer to readjust her priorities and start again. Annie sought only to start the process of adulting and this mysteriously-bestowed career seemed as good a place as any to figure out what she wanted out of life. But like Andy in Devil, she discovers that even the sentiment "wanting something out of life" is misguided in its simplistic implications about the relationship between the person and the world. Annie is slightly closer to the truth than Andy because she has been given the gift of self-agnosticism; she has less of an internal infrastructure of hopes and dreams to clear out before she is able to find her stride. The trade-off is that she spends more time trapped inside a state of fundamental suffering. But in the end, we hear in the cool, sardonic tones of her narration that this tumultuous journey has enabled her to find a perspective at a healthy remove from both her former post-college innocence and the masochistic existential confusion of the Upper East Side elite. She leverages the tools and language of academia to demonstrate the essential absurdity of the rarified worlds of the One Percent as well as the moral cockiness of those who enter their world already having made up their minds about them. The brave screenwriting choice for both of these films would have been to have their heroines choose to remain attached to their bizarre adopted social spheres, finding new morally acceptable avenues for happiness, accomplishment, and self-expression despite the cultural gaps they started out with. But sadly in both of these cases, the ultimate resolution is for them to escape back to a world closer to the ones in which they started out, albeit with a greater understanding and deeper humility about the complexities of class, success, and the world in general. Surrendering like this - to the safer, more realistic character arc - robs us of some of the profundity of the message being promoted, but still it rings clear: confusion is a perfectly natural reaction to the experience of having ivory-tower assumptions tested by the moral grime of actual human beings and the compromises that we all have to make in order to survive, both financially and ideologically. These films are not typical "message" films; they remain (mostly) dedicated throughout to colorful storytelling and characters that are easy to peg and identify with. The lessons that they teach do not resolve into focus until you rub them against each other, side by side, Flickchart style, seeing how their similarities and contrasts weave a new ontological structure between them, a structure with subtler yet more profound hypotheses about the human experience. As Andy and Annie both learned, the most meaningful lessons come from the strategic application of context to one's former assumptions. Whatever you take away from these movies after a single viewing takes on new meaning when you use each of them as context for each other, each reflecting back new facets and nuances not noticed before. Because life, at any age, is confusing, and we need all the help we can get.