Before “Legally Blonde”: Take a Look Back at Reese Witherspoon's First 15 Films

From 'The Man in the Moon' to 'Cruel Intentions,' Witherspoon has had major star power since she was a teen

Twenty-three years ago, Legally Blonde officially propelled Reese Witherspoon into Hollywood’s A-list, making her one of the biggest stars of her generation.

Since then, she’s become a major force in the entertainment business, both onscreen in films like Wild and Walk the Line (for which she won an Academy Award), and behind the scenes as a producer on films like Gone Girl and HBO’s hit series Big Little Lies.

But long before she donned a pink suit to bend-and-snap as Elle Woods, Witherspoon was a promising young actress with an impressive roster of film roles under her belt. Here, take a look back at her earliest movies — and find out where you can watch them!

'The Man in the Moon'

Reese Witherspoon made her film debut while still a teenager in 1991’s The Man in the Moon. She starred as Dani, a 14-year-old tomboy competing with her older sister (Emily Warfield) for the affections of their cute neighbor (Jason London) in this 1950s-set coming of age drama.

The Man in the Moon is currently streaming for free on Tubi.

'A Far Off Place'

In 1993, Reese Witherspoon starred with Ethan Embry as American teens who escape into Africa’s Kalahari Desert after their parents are murdered by ivory poachers in Disney’s A Far Off Place.

The film isn’t currently available to stream.

'Jack the Bear'

Jack the Bear revolves around the relationship between a widowed father (Danny DeVito) and his two sons. Reese Witherspoon had a supporting role in the 1993 film as the girlfriend of older son Jack (Robert J. Steinmiller Jr.).

Jack the Bear isn’t currently available to stream.

'S.F.W.'

Reese Witherspoon starred opposite Stephen Dorff in 1994’s black comedy S.F.W., about a disaffected teen who becomes a media sensation after surviving a kidnapping.

The film is currently streaming for free on Pluto.

'Freeway'

This twisted ’90s take on Little Red Riding Hood featured a tour de force performance from Reese Witherspoon as a wild teen runaway trying to get to her grandma’s house while evading a serial killer (Kiefer Sutherland) along the way.

Freeway is streaming now for free on Tubi, Pluto, Freevee and other platforms.

'Fear'

Reese Witherspoon played a teen caught up in a toxic relationship with a boy (Mark Wahlberg) who turns out to be violently possessive in 1996’s Fear.

The cult classic is currently streaming on Netflix.

'Twilight'

Reese Witherspoon played another teen runaway in Twilight. The 1998 thriller boasts an impressive cast, including Paul Newman, Susan Sarandon, Gene Hackman, Stockard Channing, Giancarlo Esposito and Liev Schreiber.

It’s currently available to rent on Amazon Prime Video.

'Overnight Delivery'

Long before films like Sweet Home Alabama, Just Like Heaven and Home Again, Reese Witherspoon starred opposite Paul Rudd in her very first romantic comedy. Overnight Delivery finds her playing a stripper who goes on a cross-country trip to help Rudd’s character intercept a break-up letter.

The film is currently free to stream on Tubi.

'Pleasantville'

As a popular teen transported into the world of a 1950s sitcom along with her twin brother (Tobey Maguire), Reese Witherspoon helped bring 1998’s Pleasantville to vivid, colorful life.

The film is currently available to rent on most streaming platforms.

'Cruel Intentions'

Well into her early 20s, Reese Witherspoon continued to play high schoolers, including in 1999’s Cruel Intentions. The modern take on Dangerous Liaisons set in an elite Manhattan prep school was something of a precursor to Gossip Girl, and found the star playing a virtuous teen who is pursued by bad boy Sebastian Valmont (future husband Ryan Phillippe).

Cruel Intentions is currently streaming for free on Freevee.

'Election'

Reese Witherspoon’s role as driven high school student Tracy Flick in 1999’s Election is probably one of her most iconic, becoming in recent years a stand-in for unfairly maligned ambitious women everywhere. The film earned the actress her first Golden Globe Nomination, and 2022 it was announced that a sequel, based on author Tom Perrotta’s novel Tracy Flick Can’t Win, was in development with Witherspoon slated to reprise her role.

Election is currently streaming on Max.

'Best Laid Plans'

In this twisty crime drama, Reese Witherspoon plays a young woman attempting to extort money out of a one-night stand (Josh Brolin). Let’s just say it doesn’t go according to plan.

Best Laid Plans is currently available to rent on most streaming platforms.

'Little Nicky'

Reese Witherspoon donned a pair of pink wings to play Holly, the angelic mother of Adam Sandler’s titular reluctant devil-spawn in 2000’s Little Nicky.

The outrageous comedy is currently streaming for free on Tubi.

'American Psycho'

Based on author Brett Easton Ellis’s controversial bestseller, 2000’s American Psycho features Reese Witherspoon playing Manhattan socialite Evelyn, who has no idea her fiancé (Christian Bale) is a crazed serial killer.

The film is currently streaming on Peacock.

'The Trumpet of the Swan'

The same year that Legally Blonde premiered, Reese Witherspoon voiced Serena, a beautiful swan who inspires her admirer Louie (Dee Bradley Baker) to take up the trumpet in this 2001 animated adaptation of E.B. White's The Trumpet of the Swan.

The film is currently streaming for free on Tubi.

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