A casual observer of American popular culture in the past 10 days would find it awash in contradictions, more specifically, mired in mixed messages about what we want and expect from successful women.

During the season premiere of Saturday Night Live, a skit [1] about Senator Hillary Clinton and GOP vice presidential candidate Sarah Palin skewered the public impressions of both women as it ostensibly took on the matter of sexism in the campaign. Palin (played by the awesome Tina Fey) was lampooned as a flighty, dim-witted former beauty pageant contestant who’s called a MILF and who mock-pleaded with folks to stop PhotoShopping her face onto bikini-clad images. Clinton (spot-on work by Amy Poehler) was satirized for being a more masculine, violently ambitious woman who some people called a “harpy,” who possessed a hot temper and was derided for supposedly having kankles.

Given that the skit was said by many pundits to ring true regarding the media’s perception of Palin and Clinton, what message did it send? If you’re a woman who’s perceived as too tough, too smart and too masculine, you’ll scare people? And if you’re sexy yet lipsticky-tough you’ll go farther?

The following night, I watched a new episode of Mad Men [2], a 1960s period program that centers on one surficially idyllic American family as it tackles issues of class, race, gender and casual substance abuse. The episode focused on two unmarried women who work at the Sterling Cooper advertising agency: Peggy Olson (Elisabeth Moss) in her 20s and Joan Holloway (Christina Hendricks) in her 30s.

In the first season, Olson gave birth to a baby she didn’t realize she was carrying but kept it quiet and gave the baby away on the same day she was promoted from secretary to become the only female copywriter at the firm. Olson dresses in very prim and proper clothing which sets her apart from her male peers who are dapper in their suits, drink copiously in their offices and take clients out to strip clubs. Two older professional women, both of whom exude sex appeal, advised her that in order to get ahead in business she needed to “act like a woman” not like a man which included wearing more appealing attire. While Olson rebuffed that advice and tried to be treated as an equal based on her talent, she continued to be left on the outside looking in.

Holloway, meanwhile has been portrayed as the vixen-like office manager who oversees the secretarial staff and openly uses her voluptuous sexuality (accentuated by her form fitting clothing) as a career advancement tool. However now that she’s engaged to be married, her sexual allure seems to have lost its power. She was recently undermined by a principal in the firm, with whom she used to have an affair (he “unfired” a younger, attractive secretary Holloway terminated), then, after contributing valuable insight and top-notch work on a project involving client ad placement, Holloway was surprised to be unceremoniously replaced by a (higher paid) man without even being considered for a new post instead of being sent back to oversee the steno pool.

Though Mad Men is set in the 1960s, the message delivered was that it didn’t matter how a woman looked or conducted herself in the workplace because she would be counted out regardless, unless she was her own boss, like the female head of an affluent department store last season.

With this storyline in mind, the October issue of Marie Claire [3] arrived in the mail and included an article entitled, “I am the boss of me,” featuring women entrepreneurs including: The very casually dressed president of an urban garden company, a high-heeled owner of a bowling alley, the fashionable maker of exotic candy, a flirty looking creator of a rolling alarm clock and a classic business-attired owner of a fashion boutique. Also in the same issue was a list of jobs for which a Marie Claire writer said the glass ceiling needed to be broken: A female best director Oscar winner, a woman UN secretary-general and a female astronaut who walks on the moon.

I read Marie Claire amidst the countless articles and opinion pieces recently devoted to Palin, especially a column in Reason Magazine by Cathy Young [4] who wrote, “How inspirational . . . to see that the ‘mommy track’ can be a road to the White House. Palin is a mother of five who resumed an intensive work schedule days after giving birth, and whose husband seems to be a full partner.”

As Marie Claire was praising women entrepreneurs and Cathy Young was praising working mom Palin, the premiere episode of NBC’s Lipstick Jungle [5], which airs this week (you can see it online now at the NBC web site [6]) portrayed Brooke Shields’ working mom movie studio exec as having to cut back her hours at work (even though her husband had been an at-home parent but started working more) in order to be available for her teenaged daughter who’d been getting into some trouble. Shields’ mother, played by Mary Tyler Moore, chastised her daughter for gambling with her career, saying: “You cannot be so cavalier. There are dozens and dozens of young people who would be thrilled to put in a 60-hour week.” Later, Shields’ character said to her mother, “I love my job as much as you loved yours, but it’s not the same for me . . . I want to do things differently.” And as you watch the premiere, there’s undeniably heavy foreshadowing that Shields will inevitably pay some kind of price for taking a mommy track.

What to make of all of this? The SNL skit about women pols who are perceived as either tough and masculine or sexy and flighty? The Mad Men story arc that says no matter how a woman was perceived in the 60s she’d never been as respected as men in the workplace, unless she happened to own the workplace? The Marie Claire piece praising contemporary women who actually do own their own businesses? The mommy track as a road to either the vice presidency . . . or to the movie business’ off-ramp? These are more than just a few mixed pop culture messages to absorb in a little more than a week. Perhaps, when taken together, they simply reflect our country’s confusion about what we want and what we expect our successful women to be.