The Stunning Transformation Of Reese Witherspoon

Reese Witherspoon has worn many hats during her extensive Hollywood career. As an Oscar-winning actress, her films have no-doubt brought in serious worldwide revenue. As a media mogul, her production company has created numerous female-led projects that have delivered both critical acclaim and financial success, including HBO's hit television series Big Little Lies (in which she also starred) and the big-screen thriller Gone Girl (in which she didn't).

Along the way, she's married, divorced, and remarried, all while raising children, maintaining a busy acting career, and running an empire — and appearing to have loads of fun while doing it all.

Yet Witherspoon's journey to stardom has not been an easy one. In a 2019 Instagram post she reflected on the inherent rejection faced by actors, opining that it "teaches you perseverance and how to get tough" and that "you also learn ... not every path is right for you." Find out how a plucky Southern girl went on to find the path that was right for her as she conquered Hollywood and changed the rules of its game. Read on to explore the stunning transformation of Reese Witherspoon.

Reese Witherspoon was born in New Orleans, but she spent the first few years of her life in Germany. According to Veterans Advantage, Witherspoon's father was a doctor serving as a lieutenant colonel in the U.S. Army Reserves, which required he move his family to Wiesbaden, Germany shortly after his daughter was born. Germany clearly made an impression on young Witherspoon; in 2015, she responded to a fan's Twitter question about whether she'd like to go there by responding, "We lived in Germany for 4 years! We loved it!"

When the family returned stateside, they settled in Nashville, Tenn., and Music City became her home. Nashville, she wrote in an essay for Good Housekeeping, remains the one place in the world "where I'm the happiest."

Admitting that she "fought" to shed her distinctive Southern accent when she was younger, Witherspoon revealed that she ultimately grew to appreciate everything about her childhood — "from the lessons I learned about treating people fairly to the way I was taught to tend a garden and bake a casserole."

Reese Witherspoon's interest in acting began when she was a youngster, as she revealed in an Instagram video. As she explained, her acting aspirations were "kinda weird because both my mom and my dad were in the medical industry." Yet there was no stopping her from following her dream, leading her to book her first professional acting job when she was just 7 in a local TV commercial for a florist.

Meanwhile, she was still attending school and doing all the normal things kids do, including cheerleading. In a flashback photo of of her young self cheerleading that she shared on Instagram, Witherspoon referenced her "days as a proud General." As she admitted in an interview with Cinema.com, "The only time I really fit in at school was when I was a cheerleader..."

Cheerleading remained a passion. She made that abundantly clear when she proclaimed herself to be a huge fan of the Netflix docuseries Cheer, following the exploits of the competitive cheerleading team at Navarro College in Texas. In fact, Witherspoon took to Twitter to praise Cheer as a "great show," admitting that watching the emotional finale made the one-time tween cheerleader "cry big baby tears."

Reese Witherspoon's acting ambitions did not wane as she grew older. Through a twist of fate, she wound up starring in her first movie at age 14. It all began, she told Jane, when she went to a casting call after seeing a newspaper ad seeking extras for a movie. "A month later, they sent me the script — they wanted me for a major part," she revealed. "I was in shock."

That "major part" was the lead role in The Man on the Moon, a coming-of-age story about a Southern teenage girl in the late 1950s. "It was the summer before the start of freshman year of high school and we shot all summer," recalled Witherspoon of filming, sharing the story in an Instagram video. "And it was the most magical experience." 

That summer spent filming the movie brought Witherspoon a lot of firsts, including her first movie kiss. "I had to kiss a boy onscreen for the first time," she shared, "and I was 14 years old and I was so embarrassed." She also got to attend her first movie premiere. "I remember really distinctly Arnold Schwarzenegger was at the premiere," she recalled.

As Reese Witherspoon's IMDb page indicates, The Man in the Moon catapulted teenage Reese Witherspoon into bigger and better projects. Just as her fledgling acting career was heating up, however, she hit the pause button when she was accepted into Stanford. According to Today, Witherspoon studied English literature, but she dropped out after her first year when she was offered a role in 1998's Twilight. "I had to make a choice between Psych 101 and starring in a film opposite Paul Newman, Gene Hackman, Susan Sarandon, and James Garner," she told Cinema.com. "My parents didn't quite understand my decision, but to me it was a no-brainer."

Witherspoon returned to her alma mater in 2017, when she participated in Stanford's View From the Top speaker series. While on campus, Witherspoon paid a visit to her old dorm room and delivered a surprise to its current occupant, documenting the experience on Instagram. "Surprise!" she wrote in the caption of the photo she shared, posing with the room's new resident. "While re-visiting @Stanford, I popped by my old dorm room... and met its newest tenant, Caitlyn! She was so nice; she even welcomed me in!"

After her exit from Stanford, Reese Witherspoon headed to Hollywood and began booking movie roles. The film that really put her on Tinseltown's radar was the 1998 dramedy Pleasantville, in which she starred opposite fellow up-and-comer Tobey Maguire as modern-day teenage siblings who find themselves transported into an unbearably wholesome black-and-white 1950s TV sitcom.

Her next film, however, would be life-changing. In Cruel Intentions, Witherspoon played a naive virgin who doesn't realize the handsome boy seducing her (Ryan Phillippe) is doing it to win a bet.

While filming Cruel Intentions, Witherspoon had been getting serious with co-star Phillippe, whom she originally met at her 21st birthday party (via Jane). Their relationship moved very quickly. The movie was released in March 1999, and the couple got married three months later. The newlyweds soon welcomed daughter Ava. "I got married when I was 23 and I had two kids by the time I was 27," Witherspoon told U.K. talk show Lorraine. "I had to grow up really fast, and figure out what woman I wanted to be for my daughter," she told The Hollywood Reporter.

In 2001, Reese Witherspoon was cast in arguably the most defining role of her career when she portrayed fashionista law student Elle Woods in 2001's Legally Blonde. The film was a huge hit, raking in $141 million worldwide while propelling Witherspoon to a whole new level of stardom. The film's success also provided validation for its star. "I've heard it all," she admitted in an interview with Cinema.com. "I've been told that I'm not sexy enough, not pretty enough, not smart enough, and even that I'm not tall enough to get a specific role." 

However, by no means was Witherspoon seen as a lock for Legally Blonde. According to a 2019 profile in The Hollywood Reporter, she was initially lukewarm about the movie, concerned that the character was too similar to the protagonist in the then-recently released Clueless. Meanwhile, added Witherspoon, there was opposition to her casting at the highest level. "My manager finally called and said, 'You've got to go meet with the studio head because he will not approve you. He thinks you really are your character from Election and that you're repellent,'" she said. "And then I was told to dress sexy."

The box office success of Legally Blonde and its 2003 sequel presumably opened doors for Reese Witherspoon, allowing her to branch out to more challenging roles. Her Nashville upbringing certainly didn't hurt when she was cast as country music icon June Carter in the 2005 Johnny Cash biopic Walk the Line. The role required four months of singing lessons, which she described to MTV News as "the most challenging, horrifying experience of my life." 

Both the film and her performance were praised by critics, with Rolling Stone calling the actress "hotter than a pepper sprout," while The Hollywood Reporter lauded her "knockout performance as a woman who must temper her passion with an unwillingness to witness her man's self-destruction." Witherspoon received an Oscar nomination in the best actress category, ultimately winning her first Academy Award. In her acceptance speech, she joked that she was finally able "to realize my lifelong dream of being a country music singer."

Witherspoon looked back at that moment in a 2018 Instagram post, stating, "It meant the world to me to be recognized by my peers. Overwhelmed, excited and truly humbled, I will never forget that moment."

In late 2006, People reported Reese Witherspoon and Ryan Phillippe announced they'd "decided to formally separate," and they ultimately divorced. Speaking with U.K. chat show Lorraine, Witherspoon admitted they married too young. While adamant she "would never change anything," she did advise her daughter to wait before heading to the altar, noting that it's not until age 25 that "you start to know yourself a little bit better." 

A few years after her divorce, Witherspoon met talent agent Jim Toth at a party. "It happened out of the blue," Witherspoon told Elle. "This really drunk guy was hitting on me, making such an idiot of himself, yelling at me." That, she said, was when Toth swooped in, rescuing her. "Jim came over and said,`Please excuse my friend. He's just broken up with someone.' Jim was a really good friend, pulling him out of that situation," Witherspoon shared. "That's just kind of who he is, a really good person."

The pair began dating, and Toth popped the question in 2010. In 2011, reported Hello!, the two were married in a ceremony at Witherspoon's California ranch. Numerous celebrities were in attendance, including Toth's clients Matthew McConaughey and Scarlett Johansson.

During the late 2000s, Reese Witherspoon's career stalled, and a few of Witherspoon's movies totally bombed during that time. "I was just kind of floundering career-wise, 'cause I wasn't making things I was passionate about," she told 60 Minutes. "I was just kind of working, you know. And it was really clear that audiences weren't responding to anything I was putting out there." 

She decided to take matters into her own hands by founding her own production company, Type A Films, which evolved into media company Hello Sunshine. The goal: to develop projects she was passionate about. "I'm at a point in my life, it's like, I can make 20 more movies," she added. "But I want to make 20 more movies that matter to me."

Witherspoon sought material, as reported by The Hollywood Reporter, by reading books. Her first two book-to-movie adaptations were homeruns: Gone Girl and Wild. While she planned on starring in both, Gone Girl director David Fincher bluntly told her, "It's just not you," instead casting Rosamund Pike. Any hurt feelings were surely muted by the Oscar nomination she earned for Wild and Gone Girl's $369 million worldwide gross.

In 2015, Reese Witherspoon branched out beyond the world of filmmaking into the domain of fashion, launching own clothing line Draper James. According to Forbes, she secured $17 million in investment for the brand, which celebrates her Southern heritage and is named after her grandparents, Dorothea Draper and William James Witherspoon. At the time of the company's launch, she described Draper James to the Los Angeles Times as reflecting "traditions and things that touch your heart."

Witherspoon elaborated on the philosophy behind her brand in an interview with Glamour. "You can be strong, you can be a feminist, you can be an incredibly hardworking woman — and still like pretty!" she explained. According to Witherspoon, Draper James "has a sense of humor," noting, "Fashion is too serious sometimes. ... My mother and my girlfriends and I are telling jokes and laughing all day long. That's what we try to capture in the clothes." 

Draper James proved to be an out-of-the-box hit with consumers. According to Women's Wear Daily, Draper James sold out of multiple items on the day of its launch.

After the dual successes of Gone Girl and Wild, Reese Witherspoon zeroed in her next project, an adaptation of bestseller Big Little Lies. She enlisted fellow Oscar winner Nicole Kidman to co-star, yet, as they discussed the project, Kidman felt the story would have to be too compressed to work as a movie. Witherspoon told Entertainment Weekly, "...We just really felt like we wanted to tell the story of five women, not two, and there just wouldn't be enough time within a film format to get that deep level of storytelling."

Instead of a movie, Big Little Lies became an HBO series that won critical acclaim and eight Emmys, including wins for Kidman and co-star Laura Dern and another for best limited series. As Witherspoon told the Wall Street Journal, it wasn't until the success of Big Little Lies — her third consecutive smash — that male-dominated Hollywood begrudgingly admitted her success was no fluke. "I wasn't being offered opportunities to grow my company until I got that third hit," she explained, pointing out the glaring double standard. "A guy has one hit at Sundance, and he gets Jurassic World." 

The success of Big Little Lies was a game-changer for Reese Witherspoon. Hollywood studios, she discovered, were becoming increasingly reluctant to make the kind of female-driven movies she wanted to make. As she recalled to The Hollywood Reporter, a studio exec once told her they were already making a movie "with a woman at the center of it, but we're not going to make two this year." Concurrently, Netflix and other streaming services were battling for subscribers, dangling huge paychecks to A-list talent while offering more creative control than a movie studio would.

Witherspoon realized television would provide a better platform for the stories she wanted to tell, and she'd noticed a change in the way women were consuming content. "Women weren't going to movies," she told Fast Company. "They were streaming shows. They were on Instagram and Facebook. Digital was winning. The only way was to go where women are, instead of expecting them to come to us in theaters."

It all dovetailed with her goal of creating more — and better — roles for actresses. "We women are too talented to be fighting over roles like this," she told the Wall Street Journal.

Reese Witherspoon had always been a voracious reader. She once told Cinema.com, "I was the classic nerd who was reading books all the time..." Her lifelong love of books gifted her with a keen knack for finding novels with compelling stories and characters that would translate to the screen. She took that love one step further in 2015 when she launched Reese's Book Club on Instagram, as reported by Vox, with her media brand Hello Sunshine picking it up on a more formal basis in 2017. 

The book club was a direct extension of her search for great female-focused material to bring to the screen. When she launched her company, she told IndieWire, her hunt for projects led her to start "reading voraciously" during "a time of great artistic curiosity for me." She added, "I just started reading and reading and reading."

While Witherspoon's fans no doubt enjoy delving into her book picks, Reese's Book Club has become a serious influencer in the publishing world and can drive sales substantially. As Bookscan executive director Kristen McLean told Vox, when Witherspoon picks a book to recommend for the book club, it's "the equivalent of winning the lottery for these authors."

As Reese Witherspoon told Entertainment Weekly, prior to Big Little Lies, the extent of her television experience was "being Jennifer Aniston's sister on Friends and a Lifetime movie when I was 15." In 2019, Witherspoon reunited with her former sitcom sister for The Morning Show, a big-ticket series to launch the new Apple TV+ streaming service. Focusing on a fictional network television morning show, the series starred Witherspoon and Aniston, who also served producers, and the two raked in a reported $2 million per episode apiece.

Reviews were tepid. Exec producer Mimi Leder responded by claiming those who gave the show bad reviews were "Apple haters" who hoped for Apple to "fail," as reported by Recode.

According to The Hollywood Reporter, when Witherspoon, Aniston, and the producers faced real live critics at the Television Critics Association press tour in January 2020, they were asked about that "backlash from much of the creative team." Witherspoon responded, "Look, we make product and then it is up to you guys. You have to decide how you feel about it. That's how it works." She continued, "I have no problem hearing very real opinions about material. It actually helps us make it better and work harder about parts that don't make sense."

Following the success of book-to-screen adaptations of Gone Girl for the big screen and Big Little Lies for HBO, Reese Witherspoon optioned the rights to Celeste Ng's 2017 novel Little Fires Everywhere. Once again, Witherspoon was both star and producer of a female-led project, co-starring with former Scandal star Kerry Washington (also a producer). The series was so sought-after, reported CNN, that it sparked a "bidding war" that was ultimately won by streaming service Hulu.

While the role of producer isn't as attention-grabbing as being in front of the camera, Witherspoon has come to relish being able to exercise creative control over her projects. "Choices used to be made for me a lot," she explained in an interview with Variety, noting, "There just wasn't a spectrum of storytelling for women that was reflective of the world that we walked through." She added, "I had no idea the world would open up for us."

Ahead of the series' premiere, Witherspoon issued a statement (via CNN) expressing her confidence that Little Fires Everywhere would "spur a long-overdue dialogue around race, class, and what it means to be a mother."