Reese Witherspoon (Photo by Ron Galella/Ron Galella Collection via Getty Images)/Reese Witherspoon attends the 28th Annual Screen Actors Guild Awards at Barker Hangar on February 27, 2022 in Santa Monica, California. (Photo by Axelle/Bauer-Griffin/FilmMagic)

Reese Witherspoon Then & Now: Her Life in Photos


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I think we can all agree when I say that Reese Witherspoon is one of the greatest actors of all time. I mean, that woman never sleeps! There is always something up her sleeve, coming up with things left and right. Hey, I'm not complaining. I love that woman, she oozes talent! It is so rewarding to see a woman be so successful, but at the same time so humble and hardworking.

Witherspoon was born on March 22, 1976, in New Orleans, Louisiana. The actress was raised Episcopalian and has numerously repeated that she is proud to be part of a Southern upbringing. At the early age of 7, she was selected to be a model for a florist television ad, which reportedly sparked her passion for acting.

The Man in the Moon

CIRCA 1991: Actress Reese Witherspoon and actor Jason London in a scene from the movie "The Man in the Moon", circa 1991.

Photo by Michael Ochs Archives/Getty Images

In 1991, Whitherspoon's life changed immensely, opening the door to the world of acting. The actress attended an open casting for The Man in the Moon and was cast as the lead role of Dani Trant. The actress actually spoke about her time on set, sharing with her Instagram followers that it was a "Magical experience."

She stated, "It was the summer before the start of freshman year of high school and we shot all summer, and it was the most magical experience." She continued, "I had to kiss a boy onscreen for the first time, and I was 14 years old and I was so embarrassed. I remember really distinctly Arnold Schwarzenegger was at the premiere."

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Despite her success with Man on the Moon, In 1998 Whitherspoon actually decided to take a break from her acting career. Putting acting aside, the A Wrinkle in Time actress went to Stanford to study English literature. After her exit from college, the actress began booking several movie roles, including the 1998 drama Pleasantville, starring opposite Toby Maguire.

Cruel Intentions

Reese Witherspoon and Ryan Phillipe at a luncheon

Evan Agostini/Getty Images)

In comes Cruel Intentions, which drastically changed the actor's life! Starring alongside Ryan Phillippe, Selma Blair and Sarah Michelle Gellar, the movie was officially released in March 1999. Critics praised the actress for her portrayal of Annette Hargrove. Around the same time, Whitherspoon and Phillippe were dating. They were married three months after the release of the film.

They welcomed their daughter Ava Phillippe, when Witherspoon was only 23. Speaking with the Hollywood Reporter, she stated, "I had to grow up really fast, and figure out what woman I wanted to be for my daughter.'' The couple also shares their now 18-year-old son, Deacon Reese Phillippe.

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The couple announced their separation on October 30, 2006. The actress filed for divorce, citing irreconcilable differences.

Legally Blonde

384593 09: Actress Reese Witherspoon acts in a scene from Metro-Goldwyn Mayer Pictures'' comedy "Legally Blonde.",(Photo by Tracy Bennett/MGM Pictures)

In 2001, Whistherspoon's life changed drastically after being cast as Elle Woods in one of Hollywood's biggest films, Legally Blonde. The film was so successful that it made $141 million worldwide on an $18 million budget, officially making Witherspoon an A list star. The film also stars Luke Wilson, Selma Blair, Victor Garber, Jennifer Coolidge and Mathew Davis.

The movie was nominated for a Golden Globe Award for Best Motion Picture: Musical or Comedy, and Witherspoon received a Golden Globe nomination for Best Actress Motion Picture Musical or Comedy. The success of the film quickly led to several other Legally Blonde films including a 2003 sequel, Legally Blonde 2: Red, White & Blonde and the 2009 film, Legally Blondes.

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It doesn't end there, the film actually has a musical of its own, Legally Blonde: The Musical, which premiered in San Francisco and opened on Broadway in New York City on April 29, 2007. In May 2020, the actress surprised her fans by saying that Dan Goor and Mindy Kaling were actually writing the third film. The movie, Legally Blonde 3, is planned for release in May 2022.

Sweet Home Alabama

Josh Lucas (center) and Reese Witherspoon during Reese Witherspoon and Josh Lucas filming "Sweet Home Alabama" in New York City at Soho in New York City, New York, United States.

Photo by Bill Davila/FilmMagic

In between the Legally Blonde films, the actress also found success a year later in 2002 with the romantic comedy, Sweet Home Alabama. The actress charmed the audience, staring opposite Josh Lucas, Patrick Dempsey, Mary Kay Place, Fred Ward, Candice Bergen and Jean Smart.

Throughout the years, Witherspoon has been vocal about her desire to do a sequel if the opportunity ever came up. In 2016, she stated, "We are not making a sequel that I know of, but if Disney wants to make a sequel, they can just call me. I would happily make 'Sweet Home Alabama 2.'" If I'm being biased, this is by far my favorite film Witherspoon has made.

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Walk the Line

BEVERLY HILLS, CA - JANUARY 16: Actress Reese Witherspoon and actor Joaquin Phoenix with their awards for Best Actress and Best Actor, Musical or Comedy for "Walk The Line" pose backstage during 63rd Annual Golden Globe Awards at the Beverly Hilton on January 16, 2006 in Beverly Hills, California. (Photo by Kevin Winter/Getty Images)

In 2005, the actress decided to step into another venture, showcasing her southern roots after being cast as country icon June Carter in Johnny Cash's biopic Walk the Line. The movie was a huge success, earning $22.3 million in its opening weekend and grossing $186 million becoming the highest-grossing music biopic.

Both she and Joaquin Phoenix received praise from critics, who noted that the actress put all her passion into the film. The performance was so powerful that she received an Oscar nomination for Best Actress, which was her first Academy Award win.

About playing Carter, Whitehspoon told Live About, "Well, the thing I really like about this film is I think she's a multi-faceted woman." She continued, "I don't think that she is just sort of a supportive wife. I think she goes through a lot of indecision through the process of ultimately committing to him, and I think that's more realistic for a woman."

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Water for Elephants

LOS ANGELES, CA - JANUARY 04: Jim Toth (L) and Reese Witherspoon attend a game between the Detroit Pistons and the Los Angeles Lakers at Staples Center on January 4, 2011 in Los Angeles, California. (Photo by Noel Vasquez/Getty Images)

In 2006, the actress went to star as Annie in Penelope, and later starred in the films Rendition, Four Christmases alongside Vince Vaughn, Monsters vs Aliens, How Do You Know and Water For Elephants in 2011.

Fast forward a few years, the actress began to date Jim Toth, announcing their engagement in December and marrying on March 11 in Ojai, California. The couple welcomed their son, Tennessee James Toth on September 27, 2012.

Draper James

 Reba McEntire, Reese Witherspoon, and Kacey Musgraves attend the Draper James Nashville store opening on October 28, 2015 in Nashville, Tennessee.

John Shearer/Getty Images for Draper James)

In 2015, Whitherspoon ventured out of acting, by launching her very own clothing line, Draper James. The company is said to be a nod to the actress' Southern upbringing, aiming to enhance the actress' southern roots and her own personal style. Fun fact, the name is actually a tribute to Witherspoon's grandparents, Dorothea Draper and William James Witherspoon. The company has been featured in several magazines including Vanity Fair, Coveteur, Oprah magazine, and PEOPLE.

In 2017, it was voted "Best Shop in Tennessee" by Southern Living. The line features clothes, home decor and accessories that reflect Southern living.

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Hello Sunshine

Reese Witherspoon attends the AT&T and Hello Sunshine launch celebration of "Shine On With Reese" and "Master The Mess" at NeueHouse Hollywood on August 6, 2018 in Los Angeles, California.

mma McIntyre/Getty Images for AT&T

Expanding her artistic career, in 2016 the actress decided to step into the business side, creating her own media company. Founded by Witherspoon and Strand Equity Founder Seth Rodsky, the duo created Hello Sunshine in 2016. In July of 2018, it was announced that the company was going to have its own branded cable and satellite TV channel, Hello Sunshine Channel, which focused on women.

Witherspoon has repeatedly stated that she invested in the company in order to create projects that she was very passionate about. Usually, she chooses books that are featured in her book club, Reese's Book Club x Hello Sunshine. Every month the actress announces a new book on her Instagram, aiming to bring women's stories to light. The book club is extremely successful, with over 500,00 followers on Instagram and over 70,000 on Facebook.

Hello Sunshine has produced several films and TV projects including Wild, Gone Girl, Hot Pursuit, Big Little Lies, The Morning Show, Truth Be Told, Little Fires Everywhere and more.

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Big Little Lies

 (L-R) Actors Laura Dern, Nicole Kidman, Shailene Woodley, Zoe Kravitz, and Reese Witherspoon attend the premiere of HBO's "Big Little Lies" at TCL Chinese Theatre on February 7, 2017 in Hollywood, California.

Steve Granitz/WireImage

Taking a break from the big screen, Witherspoon's next project involved several A-list celebrities, including Nicole Kidman. As the two discussed the project, they agreed that it was better off as a TV show, rather than a movie.

"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," she told Entertainment Weekly.

The first season starred Witherspoon, Kidman, Shailene Woodley, Zoe Kravitz and Laura Dern as the main characters. Other cast members include Adam Scott, Alexander Skarsgard, Jeffrey Nordling and James Tupper. For the second season, Meryl Streep joined the cast.

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It's safe to say their call was the correct one; the show, which aired on HBO, won critical acclaim and earned 16 Primetime Emmy Award Nominations, winning 8 in total, including Outstanding Limited Series. For their acting, Skarsgard, Dern and Kidman won Emmy awards and Golden Globe Awards. Skarsgard and Kidman also won Screen Actor Guild Awards for their performances.

The Morning Show

Jennifer Aniston and Reese Witherspoon attend the Apple TV+'s "The Morning Show" World Premiere at David Geffen Hall on October 28, 2019 in New York City.

Photo by Theo Wargo/Getty Images

In 2015, the actress partnered again with Jennifer Aniston, who was her sister on Friends, for The Morning Show. The series was one of the first to launch on Apple TV +'streaming service. Both actresses starred and served as producers, earning a whopping $2 million per episode each.

The first season also co-starred Steve Carell, Billy Crudup, Mark Duplass, Gugu Mbatha-Raw, Nestor Carbonell, Karen Pittman, Bel Powley, Desa nTerry, Jack Davenport, Greta Lee, Ruairi O'Connor and Julianna Marguiles. Both actresses received a Golden Globe award for Best Actress in Television Series - Drama. Carell, Aniston, Duplass and Leder received Primetime Emmy Awards Nominations, with Crudup winning Outstanding Supporting Actor in a Drama Series. Aniston received a Screen Actors Guild Award, with Carell and Crudup receiving nominations.

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The second season for the show premiered in September 2021, and it was announced it was renewed for a third season in January 2022.

Little Fires Everywhere

L-R) Liz Tigelaar, Reese Witherspoon, and Kerry Washington of "Little Fires Everywhere" speak during the Hulu segment of the 2020 Winter TCA Press Tour at The Langham Huntington, Pasadena on January 17, 2020 in Pasadena, California.

Amy Sussman/Getty Images)

Following the success of Gone Girl and Big Little Lies, the Sing actress won rights to Celeste Ng's Little Fires Everywhere. She starred and produced the series, alongside Scandal star Kerry Washington. The series, which also stars Joshua Jackson and Rosemarie DeWitt, premiered on Hulu in March 2020, consisting of eight episodes.

The series was praised by several critics, with Rotten Tomatoes giving it an approval rate of 78 percent. Hulu stated that within the first 60 days, the show was the most-watched drama ever on the streaming service. The show received a Primetime Emmy Award nomination for Outstanding Limited series, with Washington receiving a nomination for Outstanding Lead Actress in a Limited Series or Movie, and Lynn Shelton reviving a nomination for Outstanding Directing for a Limited Series, Movie or Dramatic Special. Washington also received a Screen Actors Guild Awards nomination for Outstanding Performance by a Female Actor in Television Movie or Limited Series.

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Producing Where the Crawdads Sing + New Dolly Parton Film

 Reese Witherspoon (L) and Dolly Parton attend MusiCares Person of the Year honoring Dolly Parton at Los Angeles Convention Center on February 8, 2019 in Los Angeles, California.

Photo by Kevin Mazur/Getty Images for The Recording Academy

Among Witherspoon's many current projects are producing the onscreen adaptation of the novel Where the Crawdads Sing and the film adaptation of Run, Rose, Run, Dolly Parton's novel with James Patterson. Even better? Parton herself will star in Run, Rose, Run.

Growing up in Nashville, I've loved Dolly since the moment I heard her magical voice and saw her luminous personality shine onstage," Witherspoon said in a press statement. "Beyond her magnetic presence as an artist and performer, she is one of the greatest songwriters and storytellers of our time. Her impact knows no bounds - as a musician, actor, writer, businesswoman, activist and all around incredible human being - Dolly Parton is not only an icon to me, but a true inspiration to women and girls everywhere. My admiration for her grew to even greater heights when reading Run, Rose, Run, a gripping and heartbreaking book I couldn't put down. I couldn't feel more honored to be working alongside her and James to bring this remarkable story to the screen."

 

READ MORE: 5 Celebrities Who Are Huge Country Music Fans

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