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Reese Witherspoon Has Played One-of-a-Kind So Many Times

From ‘Election’ to ‘Big Little Lies,’ Ringer staffers debate the best Reese performances

(Getty Images/Ringer illustration)
(Getty Images/Ringer illustration)

In honor of Reese Witherspoon’s transcendent work on Big Little Lies, we at The Ringer hereby declare today Reese Day. Please join us as we pay tribute to the Patron Saint of Book Clubs, Wine Clubs, and Overachievers.

‘Legally Blonde’

Hannah Giorgis: Legally Blonde is one of the best movies ever made, don’t @ me. Reese is perfect as Elle Woods, the “dumb” sorority girl who applies to Harvard in the hopes of winning back her law-school-bound jerk of a boyfriend. The movie subverts the same sexist tropes it traffics in, and Reese shines as the “surprisingly” smart Elle, a woman whom people regularly underestimate because of her love of all things stereotypically feminine. Elle’s motivation for attending Harvard is woefully misguided at first, but it makes her easier to root for: Who hasn’t done something a little outlandish for love?

Reese imbues the character with a buoyancy and bubbliness that livens up the film and challenges the way Elle’s peers view her. It’s a role meant for Reese, one in which she effectively winks through the fourth wall without ever once breaking it. Elle’s moments of triumph, both in the courtroom and outside it, carry the film — and raise Reese’s performance to the level of iconic. The courtroom scene in which Elle ensnares a lying witness by pointing out that the timeline of the woman’s hair-perming schedule doesn’t line up with standard perm practice is a stroke of genius, and Reese’s coyly calculating Elle sells it with conviction. And her delivery drives home a point that sticks longer than the curls: It’s not just Elle’s classroom knowledge that matters. Women’s interests — whether they’re calculus or cosmetics — are worthwhile, not frivolous. Who could object to that?

‘Wild’

Lindsay Zoladz: If you had to sum up Reese Witherspoon in a single sentence, you could do worse than Elle Woods’s legendary reply when her ex-boyfriend asks her how she got into Harvard Law: “What, like it’s hard?” No matter the role, Witherspoon is can-do incarnate. When she takes on a challenge, it doesn’t feel like she’s consciously trying to upend expectations so much as it is that the difficulty involved in doing so isn’t even on her radar. At no point in her career was this more apparent than when, in 2012, she announced she’d be starring in and producing Wild, the film adaptation of Cheryl Strayed’s wrenching, candid memoir about hiking the Pacific Crest Trail alone. What, like it’s hard?

Wild was an intimate labor of love: It was the first release from Witherspoon’s production company, Pacific Standard, and she struck up a close relationship to the real Cheryl Strayed, who regularly made visits to the set. The result is one of the most complex and unapologetically adult female protagonists in an American movie of the past 10 years — a triumph in an industry built on the tradition of both stereotyping and infantilizing women. It’s a warts-and-all (or maybe more to the point, rotted-off-toenails-and-all) performance, though Witherspoon never fetishizes Cheryl’s suffering; Reese imbues even her lowest moments with a toughness, a dignity. It’s a difficult role: We spend much of Wild alone with just Cheryl and her thoughts, and a less skilled actress certainly wouldn’t be able to carry a whole movie like this. Reese makes it look easy.

‘Walk the Line’

Michael Baumann: When talking about Reese Witherspoon’s best performances, the obvious place to start is the one that won her the Academy Award for Best Actress. Her Reesetastic Majesty’s June Carter kept about seven different balls in the air at all times, mothering the film’s brilliant, impulsive, self-destructive, and drug-addled protagonist, all while juggling her own career and family. (This, by the way, is what I imagine being in a movie with Joaquin Phoenix is like.) There’s a little bit of the neurotic overachiever archetype to her performance — Reese Witherspoon as historical bridge from Holly Hunter in Broadcast News to Anna Kendrick in Up in the Air — but above all else, she’s magnetic and delightful to be around. There’s a huge hole in my TV because I leapt through the screen to yell at that mean lady in the convenience store for giving June grief over getting divorced, and I will leap through the screen to yell at anyone who has a bad word to say about Walk the Line, or Reese Witherspoon’s part in creating it.

‘Good Morning America’

Kate Knibbs: Reese Witherspoon is a brilliant actor, and she is heralded for her string of plucky blonde characters, from Election’s Tracy Flick right up to her Big Little Lies role. But in my mind, the most virtuosic Witherspoon performance came when she played a contrite brunette named “Reese Witherspoon” in a 2013 Good Morning America interview shortly after she had been arrested for disorderly conduct. “We had one too many glasses of wine,” Witherspoon laments, looking chagrined and proper in a purple sheath. When she says, “I had no idea what I was saying that night!” you almost forget what she said was “DO YOU KNOW MY NAME?” while resisting arrest. Witherspoon is so good at distancing herself from herself that you come away from this interview feeling like, Aw, shucks, who among us hasn’t gotten Expert Level Hammered and verbally abused some police officers? Just leave her alone. Has anyone ever used a huge celebrity scandal to make themselves more likable more quickly?

‘Cruel Intentions’

Andrew Gruttadaro: I have a theory that Reese Witherspoon is the reason Cruel Intentions is remembered as a perfect teen movie, rather than an astonishingly offensive film about a revenge porn peddler who catches feelings. Witherspoon’s Annette Hargrove, the chaste transfer student whose virginity is the subject of a bet between stepsiblings Sebastian and Kathryn (no, seriously, this movie is absurd), validates Cruel Intentions. Her performance is so measured and lived-in that it has an osmosis effect. She convinces you to believe in Annette, but she’s also the reason you believe in Sebastian’s emotions and motivations — a nearly impossible feat, by the way, considering Sebastian is an aggressively homophobic date rapist overplayed by Ryan Phillippe. Plus, she makes this face in a scene and it’s extremely endearing:

Watching this movie now is a roller coaster. One minute Sarah Michelle Gellar’s Kathryn and Selma Blair’s exaggeratedly dumb Cecile are making out in Central Park and I’m yelling “HOW IS THIS A MOVIE?!” to no one, and the next I’m on the edge of my seat, unexpectedly invested as Annette and Sebastian roll around 950-thread-count sheets to a Counting Crows song. That’s all because Witherspoon forces you to care, even though every part of you knows you shouldn’t. That’s an extremely heavy lift, and if Cruel Intentions isn’t Witherspoon’s best performance, then we need to reexamine how we’re defining “best.”

‘Election’

Alyssa Bereznak: Reese Witherspoon is at her best playing the role of the terrifyingly ambitious suburbanite, and no other character in her canon is quite as upbeat and determined as Tracy Flick, the high schooler running for class president in the 1999 film Election. Here was a kid who arrived at school fresh-faced with perfect curls and a fold-out table, ready to collect signatures for her nomination; who raised her hand so enthusiastically that she risked throwing out a shoulder; who was willing to play dirty, to bleed for her rightful place as the head of student government; and who — minor blip, no big deal — may have had a brief love affair with a deadbeat teacher and gotten him fired. Tracy Flick was the textbook definition of a very unlikable character who trampled over others to get her way. But thanks to her unrelenting toothy grin and unflattering sweater vests, you rooted for her anyway. Election was the start of Witherspoon’s long, successful career as an actress who made you fall in love with her no matter how twisted or selfish her character was. Without the foundational Flick, we may have never been blessed with Big Little Lies’ Madeline Mackenzie — or, for that matter, that character’s excellent production of Avenue Q.

‘Inherent Vice’

Sam Schube: Inherent Vice, Paul Thomas Anderson’s adaptation of Thomas Pynchon’s weed-hazy novel, is all about paranoia: whether it’s justified, and what it might be like to have yours confirmed. In this sea of stoned, confused, and occasionally criminal characters floats Reese Witherspoon’s Deputy District Attorney Penny Kimball, a buoy of competence. (In a Pynchon property, even her name is a tell: Penny Kimball sounds forthright. Or at least more forthright than Sauncho Smilax, Esq.) Inherent Vice is a movie where people burst through doors without much of an idea of what’s on the other side. Penny, though? She sees Doc Sportello (Joaquin Phoenix) coming from a mile away:

Conspiracies are real, the movie tells us. But Reese knows that the proper way to respond to news that terrifying is to tell your sometimes-boyfriend that you two can spend the night together and pick up a pizza on the way home. In a film populated by weirdos, stoners, freaks, hippies, and fascists, she is a goddamn rock.

‘American Psycho’

Allison P. Davis: Even though Reese Witherspoon has the heart-shaped face and glossy blonde hair of an ingenue, you know she never could have played the part of American Psycho’s Jean. Jean, Patrick Bateman’s secretary and the closest thing the movie has to a true ingenue, is sweet, accommodating, and a little too lovesick and puppy-eyed to ever realize that the handsome, rich banker is a murderous sociopath. (For what it’s worth, Chloë Sevigny isn’t really ingenue material either; she’s just more convincingly oblivious.) Witherspoon can’t play sweet unless it’s a little bit sour, she can’t play naive unless it’s a lot bit cunning, and I don’t think she can play accommodating ever, which is why when she plays her version of ingenue, it results in the best sort of Reese performance — focused, manipulative, shrewd, and WASPy as all get out.

While I wish she could have just played the female version of Bateman, her turn as Bateman’s fiancée, Evelyn Williams, is as close as we can get. As Evelyn, Witherspoon played the perfect measured New York society girl — pearls, polo shirts, and the rest. Her character definitely was a killer on the tennis court, definitely had a cotillion, and definitely blew someone else’s date on the tennis court at said cotillion. She’s determined to marry the right sort of man — she recognizes he’s probably truly awful, but it doesn’t matter because it’s part of her plan. Take her best scene in the movie: She’s in a perfect ice-blue jacquard skirt suit, a headband, and pearls. She’s snappily demanding Bateman commit to a wedding while at lunch at a high-class ’80s (i.e., aesthetically revolting) hot spot. He tries to break up with her. She refuses. “My friends are your friends and your friends are my friends,” she says pragmatically. “That won’t work.” And when he finally makes her realize he’s serious, she doesn’t go quietly, and she doesn’t endure the heartbreak weepily and gently. Instead she gets hers — in this case by doing the worst thing a WASP can do to another WASP. She makes a scene.

Yes, the path of every ingenue, even a Witherspoon ingenue, is the same: They just want love. The difference between her and the garden-variety version is that if you stray from the path, she will mess you up with a sweet smile.

‘Saturday Night Live’

Rob Harvilla: Reese Witherspoon is an American hero for hosting the single Saturday Night Live episode where the person hosting mattered the least: September 29, 2001, the first show after 9–11. It’s famous now for its somber-yet-triumphant cold open — Rudolph Giuliani flanked by members of the New York Police, Fire, and Port Authority Departments as Paul Simon played “The Boxer” — and basically nothing else. From that intro, it was almost preferable that nothing remarkable happen: a slow, cheerful, anonymous immersion back into our old cultural routines. You needed a headliner willing to be a bit player, a straight man, an anonymous celebrity therapist willing to let everyone else talk.

Reese was happy to oblige. She did a D+ Anne Heche impression on Celebrity Jeopardy!; she sang, “I feel an increased flow of mucus in my fish genitalia” in a clamshell bikini opposite Will Ferrell in a pornographic Little Mermaid goof. She almost swore in her monologue just to cheer everyone up, but decided against it. Nothing she did mattered in the slightest, but the fact of her being there was vitally important. The show had to go on, and it needed a very famous and totally selfless person to revolve around, to wrap us in a bear hug but not jostle us in the slightest, not yet. You likely don’t remember anything she did, and she likely knew that would be the case even at the time. But don’t ever forget that she did it anyway.

‘Fear’

Katie Baker: I am lucky to have many blessings: a nice landlord; a mostly cute toddler; coworkers who share my sick fascination with Jeremy Renner. But the thing I am most thankful for is that I was born in 1983 — positioning me as a newly teenaged middle schooler at the exact moment the seminal film Fear was released. I’m not sure how many times we watched the VHS of this movie during sleepovers in my friend Julia’s basement, but I do know that I learned so, so much in the process: about the downward spiral of an abusive relationship; about Bush; about Pacific Northwest real estate; about optimal carnival fingerbanging; and about the extremely specific way Alyssa Milano spoke the lines “some old coot in San Francisco with a potbelly and a lotta dough.” I also learned about how much I wanted to be Nicole Walker, as played by Reese Witherspoon.

For us, then, Fear was weirdly aspirational for a film in which a dog gets decapitated and a bare hand gets power-drilled. And it was my first exposure to Queen Reese, a couple of years before the back-to-back-to-back PleasantvilleCruel IntentionsElection trio made her a true household name. I loved her so much. Nicole was in high school, first of all, and we all admired her crop tops and ability to lie to her father so she could go make out with a probable felon. We may have been cruelly shackled by the nuns chaperoning our own middle school dances, but Nicole was out there living the dream at a rad Seattle rave while getting hit on by a guy playing pool in a tight black shirt. We may have obsessed over prepubescent boys, but grown men played by Marky Mark (described in an L.A. Times review as looking “like a paroled sex offender, one who did not ask to be castrated before his release”) obsessed over Nicole (described in an Entertainment Weekly review as having “the look of an erotic star child”).

That last phrase is somehow creepier than anything in the movie, but it is also correct. When I revisited Fear a few years back — no longer younger than the virginal protagonist and no longer lying on a duvet-strewn floor in a New Jersey McMansion — I was borderline shocked. Reese was 19 when Fear was filmed, but onscreen she is just a tiny baby victimized by a grown monster and played by a captivating actress. It was much harder to watch. I was no longer jealous of Nicole’s life, and I could finally understand why her dad was so freaking intense.

‘Pleasantville’

K. Austin Collins: Let it be known that it was Reese Witherspoon who single-handedly brought color to the black-and-white town of Pleasantville. That isn’t quite how I’d remembered Pleasantville, Gary Ross’s 1998 movie about a modern pair of teenage siblings, played by Witherspoon and Tobey Maguire, who get trapped in the socially restrictive world of a Leave It to Beaver–esque TV show. I’d remembered Reese getting laid by a boy named Skip while parked on Lover’s Lane. And I’d recalled that in the world of Pleasantville, where the worst thing that ever happened was a cat getting stuck on a high branch, forays into sex were a novel thing, so much so that orgasms made this family-friendly, monotone ’50s universe burst, literally, into vibrant color.

But, like, Reese did that. That’s the part I hadn’t quite remembered: just how singularly her “bad girl” character’s natural desire to sleep with the hottest boy in a fictional ’50s town would flip the world of Pleasantville on its axis. For Reese’s Jen, being stuck in Pleasantville means going from tight tanks and cigarette breaks in her modern high school parking lot to a world where girls wear sweater sets and poodle skirts as if by law. She’s chaos in a world of order: She crash-lands in this town, leaving modernity — sex, color, words like “cool” — in her wake.

As far as Pleasantville is concerned, Jen is rock ’n’ roll. Of course, then, she’s a prime role for Reese, who, though always a larger-than-life force, rarely gets to embody one so literally. It’s a perfect role, too, for summing up every quality represented by Reese’s signature ’90s characters: the vain, popular, dark, easily underestimated girl, on one hand, and the honest-to-goodness, bubbly, lively, good girl on the other. Reese’s best roles through the early aughts always struck some balance between the two (Tracy Flick is bubbly but dark; Elle Woods is vain but incredibly good), but only Pleasantville makes a point of peeling them apart.

‘Big Little Lies’

Alison Herman: Big Little Lies was made for Reese Witherspoon, by Reese Witherspoon. Reese optioned the Liane Moriarty novel on which the show is based. Reese has an executive producer credit on the final product. Reese brought on Jean-Marc Vallée, who’d previously directed her to an Academy Award nomination in Wild. With Big Little Lies, Witherspoon custom-built her own stage. Is it any surprise she’s doing the best work of her career on it?

The resemblance of Madeline Martha Mackenzie — say that five times fast — to past Witherspoon roles has been widely noted. The type-A neuroticism, the manic performance of a certain kind of femininity, the comedy of that performance’s inevitable slippage: Madeline carries all of them with her at all times, packaged neatly into her Longchamp. She’s a walking greatest-hits collection, Reese giving her all with Reese as her muse.

Witherspoon is just 41, so her career is far from its crescendo (especially since, as Big Little Lies proves, she’s one of few women in Hollywood with the muscle to get a showcase like this made). Still, Big Little Lies feels like the culmination of something. This is a performer with such a shrewd knowledge of her own strengths that she’s engineered the perfect vessel for them. How can she go back to a Tracy Flick or Elle Woods from here? The only thing Reese Witherspoon can do after epitomizing Reese Witherspoon is become something else entirely.