In 2001, Legally Blonde—a romantic comedy about a ditzy L.A. fashion-merchandising major who follows her ex-boyfriend to Harvard Law—opened at No. 1, grossed nearly $142 million, and planted its star, Reese Witherspoon, squarely on Hollywood’s A-list and in the echelons of the $20 million paycheck.
Six years later, following her 2006 Oscar win for Walk the Line, Witherspoon topped Hollywood Reporter’s highest-paid-actresses list. Then, well... Remember Just Like Heaven? How Do You Know? This Means War? Didn’t think so.
On a flight in 2011, her career mired in a rom-com rut, Witherspoon read an advance copy of Wild, Cheryl Strayed’s soon-to-be-published memoir about her trek along the Pacific Crest Trail. The actress was into the story and, perhaps more so, into the public-perception shift. (A video of her disorderly conduct arrest in 2013 went viral and helped her shake the squeaky-clean image too.) After that flight, Witherspoon started the production company Pacific Standard, optioned Wild, and in 2015 got her second Oscar nomination for her role in the film adaptation. And while Witherspoon began to make better movies for herself, she also established her bona fides as having one of the best eyes in Hollywood.
She bought the rights to Gone Girl before it was published. It became both a best seller and an Oscar-nominated hit. (She even had the good sense to let the lesser-known Rosamund Pike play the lead.) She scooped up Liane Moriarty’s best seller Big Little Lies, which became a limited series earlier this year on HBO. (Again, she gave the juiciest part to Nicole Kidman.) On deck: Moriarty’s Truly Madly Guilty and Jessica Knoll’s Luckiest Girl Alive. (Witherspoon’s Instagram posts on what she reads immediately affect Amazon rankings.)
Sure, Witherspoon is still capable of the occasional misstep—why, oh why Hot Pursuit with Sofía Vergara?—and she still doesn’t get everything she wants. (She lost out to Steven Spielberg on Lynsey Addario’s war-photographer memoir, It’s What I Do, which will star Jennifer Lawrence.) But her most surprising role yet may be that of mogul. She has compared her career trajectory with that of her Legally Blonde character. “Like Elle Woods,” she says, “I do not like to be underestimated.”