In an interview with The Hollywood Reporter for its 2019 Women in Entertainment issue, the Oscar winner recalled the challenges she endured to get the lead role which would skyrocket her into superstardom.
According to Witherspoon, her memorable performance in "Election" two years prior put her at risk of being typecast.
"They thought I was a shrew," she said. "My manager finally called and said, 'You've got to go meet with the studio head because he will not approve you. He thinks you really are your character from 'Election' and that you're repellent.' And then I was told to dress sexy."
If that weren't enough, Witherspoon was caring for her daughter Ava Phillippe, who was just a baby at the time.
"And you're 23, you have a baby at home, you need the money and you're being told that by people who know what they're doing," she recalled. "It's funny to think of all the things we were told to do back then because now you're thinking, 'Oh God, if somebody told my daughter to do that, she'd be like, I really hope you're joking.' "
Not unlike Elle Woods herself, Witherspoon preserved. Amid the audition process, Witherspoon met with executives in character, even putting on a Southern California accent.
"I remember a room full of men who were asking me questions about being a coed and being in a sorority," she said. "Even though I had dropped out of [Stanford University] four years earlier and I have never been inside a sorority house."
Luckily, the hard work paid off. Not only did Witherspoon get the role in the now-iconic comedy, but the film made $142 worldwide. The "Legally Blonde" sequel also found success two years later and brought in a whopping $125 million.
Her career hasn't slowed since. In addition to her acting career -- with accolades for "Big Little Lies" and "The Morning Show" -- she also has a production company and clothing line. She's also still set to co-produce and star in "Legally Blonde 3," which is slated for a 2020 release.