After starring in the 1996 films Freeway and Fear, her breakthrough came in 1999 with a supporting role in Cruel Intentions, and for her portrayal of Tracy Flick in the black comedy Election.

[27] In 1996, Witherspoon starred in two major films: the thriller Fear alongside Mark Wahlberg,[28][29] as Nicole Walker, a teenager who starts dating a man with obsessive tendencies, and the black-comedy thriller Freeway, alongside Kiefer Sutherland and Brooke Shields, in which she played Vanessa Lutz;[30] a poor girl living in Los Angeles who encounters a serial killer on the way to her grandmother's home in Stockton.

[15] The film received positive reviews from critics; San Francisco Chronicle's Mick LaSalle wrote, "Witherspoon, who does a Texas accent, is dazzling, utterly believable in one extreme situation after the other.

[23] A year later, Witherspoon co-starred with Alessandro Nivola in the drama thriller Best Laid Plans; she played Lissa, a woman who schemes with her lover Nick to escape a small dead-end town.

[6] Also in 1999, she co-starred with Sarah Michelle Gellar and Ryan Phillippe in the drama Cruel Intentions, a modern version of the 18th-century French novel Les Liaisons Dangereuses.

The critic for San Francisco Chronicle praised her performance as Annette Hargrove: "Witherspoon is especially good in the least flashy role, and even when called upon to make a series of cute devilish faces, she pulls it off.

[44] Meanwhile, the Seattle Post-Intelligencer concluded, "Witherspoon is a talented comedian who can perk up a scene just by marching in full of pep and drive and she powers this modest little comedy almost single-handedly.

The Miami Herald called it "a romantic comedy so rote, dull and predictable",[51] and the press opined that Witherspoon was the only reason the film attracted such a large audience.

USA Today considered the movie "plodding, unfunny and almost cringe-worthy", but also wrote "Reese Witherspoon still does a fine job portraying the fair-haired lovable brainiac, but her top-notch comic timing is wasted on the humorless dialogue.

"[62] The Charlotte Observer called her work "an excellent performance that's soft around the edges", and the Los Angeles Times concluded that Becky is "a role Reese Witherspoon was born to play".

Her character, Elizabeth Masterson, is an ambitious young doctor who is involved in a car accident on her way to a blind date and is left in a coma; her spirit returns to her old apartment where she later finds true love.

Reflecting on this period of time in a December 2014 interview, Witherspoon attributed it to the split from her first husband in October 2006 and their subsequent divorce, stating that she spent "a few years just trying to feel better.

In the first, she was cast in James L. Brooks' How Do You Know,[91][92][93] in which she played a former national softball player who struggles to choose between a baseball-star boyfriend (Owen Wilson) and a business executive being investigated for white-collar crime (Paul Rudd).

Directed by McG and released by 20th Century Fox, This Means War, saw Witherspoon's character at the center of a battle between best friends (played by Chris Pine and Tom Hardy), who are both in love with her.

[104][105][106] The film was panned by critics, with a 25% approval rating on Rotten Tomatoes,[107] and fared poorly at the box office, taking fifth place on its opening weekend with sales of $17.6 million.

[109] In September 2011, a year after beginning work on This Means War, she filmed a small role in Jeff Nichols's coming-of-age drama Mud in Arkansas, playing Juniper, the former girlfriend of a fugitive (Matthew McConaughey), who enlists two local boys to help him evade capture and rekindle his romance with her.

[115][116] Witherspoon next starred in Devil's Knot, which was directed by Atom Egoyan, and based on the true crime book of the same name, examining the controversial case of the West Memphis Three.

In an interview subsequent to her casting in the film, Egoyan noted that although the role requires "an emotionally loaded journey," he "met with Reese, and... talked at length about the project, and she's eager to take on the challenge.

[136] Witherspoon appeared in Philippe Falardeau's drama The Good Lie, based on a true story about an employment counselor assigned to help four young Sudanese refugees, known as Lost Boys of Sudan, who win a lottery for relocation to the U.S.[137][138] It was released on October 3, 2014.

[141][142] In May 2014, Witherspoon began production in Louisiana on Hot Pursuit, a comedy in which she plays a police officer trying to protect a drug lord's widow (Sofía Vergara).

[145] That same year, Witherspoon began filming her first television project since 1993's Return To Lonesome Dove, the seven-part miniseries adaptation of the Liane Moriarty bestseller, Big Little Lies.

[159][160] Witherspoon also serves as an executive producer for the Apple TV+ series Truth Be Told starring Octavia Spencer which premiered in December 2019; it was renewed for a second season in March 2020.

[161][162][163] In 2020, Witherspoon produced and starred in the Hulu drama miniseries Little Fires Everywhere opposite Kerry Washington, the televised adaptation of Celeste Ng's 2017 novel of the same name.

"[7] In March 2012, Witherspoon merged Type A Films with Bruna Papandrea's "Make Movies" banner to form a new production company called Pacific Standard.

[172] Pacific Standard has since become a subsidiary of Hello Sunshine, a firm co-owned by Witherspoon and Otter Media, focused on telling female-oriented stories through film, television and digital channels.

Witherspoon stated that she was "excited to work as a creative partner alongside the Elizabeth Arden team, producing content that celebrates the spirit of the brand, highlighting female-centric stories that illustrate women's true life experiences which unite us all".

[181] Explaining her motives for joining the foundation, she said, "As a woman and a mother I care deeply about the well being of other women and children throughout the world and through the years, I have always looked for opportunities to make a difference.

[213] That year, she was awarded, by the committee's unanimous vote, the American Cinematheque for being "a perfect example of an actress flourishing in today's world" and "an active and successful movie producer who is moving her career forward both behind and in front of the camera".

"[245] Witherspoon has cited Jodie Foster, Meryl Streep, Holly Hunter, Susan Sarandon, Frances McDormand, Debra Winger, Diane Ladd, Julia Roberts, Nicole Kidman, Jennifer Aniston, Goldie Hawn, Sally Field, Sigourney Weaver, Lucille Ball, Carole Lombard, Judy Holliday, Gena Rowlands, Tom Hanks, Jack Nicholson, and Michael Keaton as influences on her acting career and work.

[247][250][251][252] Witherspoon's most acclaimed and highest-grossing films, according to the review aggregate website Rotten Tomatoes, include Election (1999), Legally Blonde (2001), Walk the Line (2005), Monsters vs. Aliens (2009), Mud (2013), Wild (2014), and Sing (2016).