Madonna is a musician and pop-culture icon who Gilbert references throughout the early chapters of the text. Gilbert particularly examines her work in comparison to the ways early-aughts culture represented female desire and sexuality in the media. In Chapter 1, Gilbert asserts that Madonna’s “Justify My Love” song and accompanying music video “set the tone for the coming decade: audacious, wildly sexual, a little bit trollish” (2). This work disrupted previous representations of female fantasy and desire in an unprecedentedly brazen manner. The song and video came out in 1990, near the height of the AIDS epidemic, and was a reaction to the concurrent anti-sex campaigns and schools of thought.

Gilbert holds that Madonna’s work challenged the male gaze, suggesting that women did not need to perform and create work according to men’s desires or for male pleasure. Gilbert identifies Madonna as one of the most pro-sex figures of her time and calls her work groundbreaking on many counts. She traces a connection between Madonna’s music and performances and the uptick in pornographic representations of women in 2000s culture. While her book Sex was shocking for its time, Gilbert retrospectively questions how much of the book’s influence was in fact due to “Madonna’s extraordinary level of fame at the time” (42). Madonna’s work did disrupt some cultural stereotypes of women but also reinforced postfeminist notions of exhibitionism and licensed “more and more sexual provocation in conventional media” (42).

Terry Richardson is a fashion photographer whose work and influence Gilbert explores most notably in Chapters 2 and 6. Richardson’s work appeared on the cultural stage in 2004 when “the Deitch Projects gallery in downtown New York debuted a splashy exhibition of [his] new work […] accompanied by the publication of a book, both titled Terryworld” (27). Until these public presentations, Richardson was known for his intentionally tacky photographic aesthetic. His photographs of celebrities were shot in the same way he photographed laypeople—giving the famous and the anonymous “the same high-flash, semisurprised, not-quite-human aura” (27). Richardson’s Terryworld exhibition won him new attention because this work featured images of Kate Moss, Pharrell Williams, and Dennis Hopper. The Terryworld publication was a coffee-table book, which encapsulated the era’s porno chic aesthetic. The photos were gregarious and bold, but also flattened their subjects.

Gilbert heavily references Richardson’s work within the context of her discussion of pornography and early-aughts culture. She holds that Richardson was of notable influence to this trend, normalizing pornographic imagery in the fashion world and advertising at large. Gilbert presents Richardson as a brash character whose public demeanor mirrored the unabashed, unaffected nature of his work. More than simply normalizing sex in fashion and the media, Richardson implied that every person has violent sexual fantasies and brutal sexual tendencies. His commentary on Abu Ghraib is reflective of this stance. Gilbert presents Richardson’s cultural influence as essential to how women were taught to see themselves and other women throughout the aughts.

Lena Dunham is a comedian, writer, and actress. Gilbert examines her work throughout Chapter 8 to develop her theme of Feminism’s Push for Diverse and Authentic Representations of Women. Gilbert asserts that the release of Dunham’s 2010 film Tiny Furniture launched an onslaught of similar autofictional work by women. In Tiny Furniture, Dunham used her own post-college experience to challenge postfeminist notions of womanhood and femininity. In the film, the protagonist Aura—played by Dunham herself—is “a recent Oberlin grad returning to her mother’s austere Tribeca loft after her boyfriend breaks up with her”; no job, money, or prospects, Aura is struggling to launch her creative career from a single YouTube video where “she strips to her underwear and grooms herself in a campus fountain” (201). Elements of the Tiny Furniture narrative were directly drawn from Dunham’s life, but the film uses experimentation to imply that “there is no happy ending […] Only an enlightened realism” (205).

Dunham is best known for her television series Girls, which expounds upon similar themes to Tiny Furniture. Beginning in 2012, the show focuses on the protagonist Hannah’s experiences with art and sex. The show also traces the lives of Hannah’s three best friends, navigating their early twenties in New York City. Gilbert argues that although the show can be seen as exhibitionist, it does not try to sell its viewers any products or lifestyles the way most postfeminist work would. The show is at once antisocial, rebellious, and gritty, and has received notable criticism since it originally aired. Gilbert offers detailed renderings of scenes and subplots from the show, using these descriptions as throughways to her wider cultural commentary.

Dunham has received much public criticism for her work and for her unabashed self-presentation within it. Gilbert argues that public reaction to Dunham’s naked body reveals the narrow lens through which women have historically been seen. Women who look like Dunham typically aren’t allowed such visibility, particularly when voluntarily exposing themselves.

Gilbert also compares Dunham’s work to that of the Canadian author Sheila Heti, to explore how women artists in the late aughts were working to disrupt the shaming culture of the years preceding. Gilbert intentionally resists criticizing Dunham on the page, so as not to participate in the divisive culture that has sought to push Dunham to the margins of her field.