Will we ever get tired of Clueless? Ugh, as if! Acclaimed pop culture journalist Jen Chaney celebrates the twentieth anniversary of the classic film’s release in the first book of its kind, weaving together original interviews with writer and director Amy Heckerling; key cast members, including Alicia Silverstone (Cher), Paul Rudd (Josh), Stacey Dash (Dionne), Donald Faison (Murray), Elisa Donovan (Amber), Wallace Shawn (Mr. Hall), Twink Caplan (Ms. Geist and associate producer); and other crucial Clueless players like costume designer Mona May, casting director Marcia Ross, director of photography Bill Pope, former Paramount chairwoman Sherry Lansing, and many more. Cast and crew also pay heartfelt tribute to the late Brittany Murphy, who lit up the screen as Cher’s protégée, Tai. Chaney explores the influence of Jane Austen’s Emma as the unlikely framework for Heckerling’s script, the rigorous casting process (including the future stars who didn’t make the cut), the functional yet fashion-forward wardrobe, the unique slang that drew from the past and coined new phrases for the future, the sun-drenched soundtrack that set the tone, and—above all—the massive amount of work, creativity, and craft that went into making Clueless look so effortlessly bright and glossy. As If! illuminates why plaid skirts and knee socks will never go out of style, and why Clueless remains one of the most beloved comedies of all time.