Reese Witherspoon has come a long way since her breakout role as Elle Woods in Legally Blonde. Over the years, she’s evolved not only as an actress but also as a producer, businesswoman, and advocate for women in media.
#1. The Man in the Moon (October 1991)
Witherspoon made her movie debut as Dani Trant in The Man in the Moon.
#2. Pleasantville (October 1998)
Her role as Jennifer in Pleasantville helped further her career.
#3. Cruel Intentions and Election (Spring 1999)
She turned heads with Cruel Intentions and Election, establishing her as a rising star.
#4. Marriage to Ryan Phillippe (June 1999)
Witherspoon tied the knot with her Cruel Intentions co-star Ryan Phillippe.
#5. Birth of Daughter Ava (September 1999)
She and Phillippe welcomed their daughter, Ava.
#6. Friends Cameo (February 2000)
She guest-starred as Jill Green, Rachel Green’s sister, on two episodes of Friends.
#7. Launch of Type A Films (2000)
Witherspoon launched her production company, Type A Films.
#8. Legally Blonde (July 2001)
Her portrayal of Elle Woods in Legally Blonde turned her into a Hollywood powerhouse.
#9. Sweet Home Alabama (September 2002)
Witherspoon’s southern charm shone as Melanie Smooter in Sweet Home Alabama.
#10. Producing Legally Blonde 2 (July 2003)
Legally Blonde 2: Red, White & Blonde marked her debut as a producer.
#11. Birth of Son Deacon (October 2003)
Witherspoon and Phillippe welcomed their second child, son Deacon.
#12. Academy Award Win (March 2006)
Witherspoon won her first Academy Award for Best Actress for Walk the Line.
#13. Divorce from Ryan Phillippe (October 2006)
The couple announced their split, finalizing their divorce in 2008.
#14. Breakup with Jake Gyllenhaal (December 2009)
After three years together, Witherspoon and Jake Gyllenhaal called it quits.
#15. Hollywood Walk of Fame (December 2010)
She received her star on the Hollywood Walk of Fame.
#16. Marriage to Jim Toth (March 2011)
Witherspoon married Jim Toth in a small ceremony in Ojai, California.
#17. Birth of Son Tennessee (September 2012)
Witherspoon and Toth welcomed their son, Tennessee.
#18. Legal Troubles (April 2013)
Witherspoon was arrested in Atlanta with Toth, who was charged with a DUI. Witherspoon faced a disorderly conduct charge.
#19. Wild and Oscar Nomination (December 2014)
Witherspoon was nominated for an Oscar for her performance in Wild.
#20. Launch of Draper James (May 2015)
She launched her clothing line Draper James with a flagship store in Nashville.
#21. Founding Hello Sunshine (Fall 2016)
Witherspoon co-founded Hello Sunshine, aiming to empower women by giving them a platform to tell their stories.
#22. Sing (December 2016)
She voiced Rosita in Sing and reprised the role in Sing 2 in 2021.
#23. Big Little Lies (February 2017 to July 2019)
Big Little Lies ran for two seasons, winning multiple Emmys. Witherspoon starred as Madeline and served as an executive producer.
#24. Launching Reese’s Book Club (May 2017)
Witherspoon launched Reese’s Book Club, recommending monthly reads to her fans.
#25. Whiskey in a Teacup (September 2018)
Witherspoon penned Whiskey in a Teacup, sharing recipes and tips from her upbringing.
#26. The Morning Show (November 2019)
Witherspoon reunited with Jennifer Aniston for The Morning Show. She earned an Emmy nomination for her role.
#27. Little Fires Everywhere (March 2020)
Witherspoon and Kerry Washington co-starred in Hulu’s Little Fires Everywhere.
#28. Legally Blonde 3 Announcement (May 2020)
Witherspoon confirmed that Legally Blonde 3 was in the works with Mindy Kaling as one of the writers.
#29. Your Place or Mine (February 2023)
Witherspoon and Ashton Kutcher teamed up for the Netflix rom-com Your Place or Mine.
#30. Divorce Announcement (March 2023)
Witherspoon announced her separation from Jim Toth after 12 years of marriage. Four months later, the pair finalized their divorce.
