New Orleans native Reese Witherspoon is one of the hardest-working people in Hollywood. This Oscar-winning actor, producer, and advocate has created an impressive career for herself while also forging new paths for female actors. Witherspoon helms Hello Sunshine productions, which seeks to establish more viable roles for women in the film and television industries.

While Witherspoon’s acting credits include many rom-coms, she often returns to the dark and compelling roles that defined the early days of her acting career. This list gathers 5 dynamic performances from the 1990s Reese Witherspoon, as well as 5 more from modern times.

Then: S.F.W. (1994)

This black comedy, which also stars Stephen Dorff and Jake Busey, provides a scathing critique of the celebrity-obsessed media that began ruling the airwaves in the 1990s. Dorff plays Cliff, one of many held hostage by a group of terrorists who take over a convenience store. The incident, which lasts a month, is recorded by the terrorists, who demand it be broadcast on national TV.

Witherspoon plays Cliff’s girlfriend, Wendy, who, along with her beau, becomes famous on the talk show circuit, selling stories about the hostage situation. While S.F.W. didn’t receive the hype and attention of films with similar themes like Natural Born Killers, it still exposes the unique brand of 1990s nihilism shared by many young people.

Now: Walk The Line (2005)

Witherspoon won an Oscar for her portrayal of June Carter in this fascinating biopic about the courtship between Carter and her future husband, country legend Johnny Cash. Joaquin Phoenix plays Cash, and both actors received critical acclaim for their performances.

Carter and Cash met in the early days of the latter’s career. She was a member of the famous Carter family, and their union gave Cash the support he needed to excel until drugs and alcohol got in the way. Both Phoenix and Witherspoon did their own singing in the movie.

Then: Freeway (1996)

This gritty and violent black comedy is inspired by the classic tale of “Little Red Riding Hood.” Witherspoon plays a poor teenager living in Los Angeles named Vanessa. Vanessa’s mother is a drug addict, and her stepfather is abusive. When they are arrested for various indiscretions, Vanessa decides to skip town in her case worker’s car in search of her long-lost grandmother.

Eventually, she crosses paths with a man named Bob, played by Keifer Sutherland, who claims to be a youth counselor. Vanessa soon realizes Bob is a serial killer who has been maiming women up and down Interstate 5, and she is forced to fight for her life yet again. Witherspoon gives a fierce and absorbing performance as a young woman who has all the cards stacked against her in life.

Now: Mud (2012)

This Jeff Nichols gem follows a pair of young friends who discover a man hiding out in a small island on the Mississippi River. Matthew McConaughey plays the title character Mud, who is on the run from bounty hunters after he killed a man in Texas.

Witherspoon plays his true love, Juniper, who is also implicated in the murder. She’s hiding out in a hotel on the outskirts of town, waiting for Mud to make a move so they can escape together. Mud is a beautiful portrait of the roughness that comes with living along the Mississippi Delta, a Southern gothic tale for modern times.

Then: Overnight Delivery (1998)

While technically a rom-com, Overnight Delivery is one of those 1990s flicks that manages to provide a fresh perspective on the genre. Witherspoon stars alongside Paul Rudd. The latter’s character, Wyatt, hears from a friend that his girlfriend is cheating on him. Heartbroken, Wyatt gets drunk at a strip club and becomes acquainted with a dancer, Ivy, played by Witherspoon. She manages to give Ivy an edge that saves the character from stereotypes often associated with sex workers.

Wyatt decides to send his girlfriend, who attends college thousands of miles away in Memphis, an overnight package that includes a scathing letter and a polaroid of him with Ivy. When he wakes up the next morning to find out the rumor about his girlfriend might not be true, he goes on a crazy cross-country adventure with Ivy to retrieve the package before it arrives in Memphis.

Now: Wild (2014)

One of the first films produced by Witherspoon’s Hello Sunshine company, Wild also helped revive Witherspoon’s career. After struggling to find interesting, challenging roles, Witherspoon decided to take matters into her own hands. It paid off. Wild was critically acclaimed and landed Witherspoon an Oscar nomination.

Based on the memoir by Cheryl Strayed, Wild focuses on the woman’s decision to work through her inner demons by embarking on a 1,000 plus mile hike along the strenuous Pacific Crest Trail. As she ventures deeper and deeper into the wilderness, she is forced to face all of her traumas head-on.

Then: Pleasantville (1998)

A smart satire about the false mid-century American ideals marketed in 1950s television, Pleasantville stars Witherspoon and Tobey Macguire as two teens living in the 1990s who magically find themselves transposed into the world of an iconic, old television series.

While Macguire’s character loves the simplicity and evenness of life in Pleasantville, Witherspoon begins to undermine the status quo, which causes the facade to fall apart. Desires surface, parts of the city of start to bloom in color, and the town’s residents begin to challenge each other in new and exciting ways.

Now: Big Little Lies (2017 - 2019)

Witherspoon acts and serves as executive producer in this ensemble HBO drama based on a novel by Liane Moriarty. Big Little Lies focuses on a group of women living in Monterey, California, who becomes involved in a murder investigation.

Nicole Kidman, Shailene Woodley, Laura Dern, and Zoë Kravitz star alongside Witherspoon. The series digs into toxic masculinity, abusive partners, and intergenerational trauma while maintaining a soap opera-esque tone. Alexander Skarsgard, Adam Scott, and Meryl Streep also have supporting roles.

Then: Election (1999)

Election is a dark and hilarious comedy about high school directed by Alexander Payne. Witherspoon’s most famous role from the 1990s may be Tracy Flick, an overachieving student at an Omaha, Nebraska high school who decides to run for student body president.

Her popular social studies teacher, Mr. McAllister, played by Matthew Broderick, finds Tracy’s demeanor and habits annoying, and he decides to undermine her election, believing another student should rise to the top. Witherspoon’s portrayal of a young and goal-oriented woman whose life is frustrated by the older men around her is engrossing, and she plays on Tracy’s idiosyncrasies in a way only a skilled actor could.

Now: The Morning Show (2019 - )

One of Witherspoon’s latest ventures, The Morning Show is another ensemble drama that debuted on Apple TV+ in 2019. She stars alongside Jennifer Aniston, Steve Carrell, and Billy Crudup in this series about the minds and faces involved in the making of a popular Manhattan news show.

Witherspoon plays a field reporter named Bradley Jackson who engages in a rivalry with Aniston’s character Alex Levy, one of the show’s daily anchors. The show shines a light on sexual misconduct scandals and the brutal, cut-throat nature of even the fluffiest news shows.