3. Anna Scott in Notting Hill (1999) 

Like Julianne Potter, Anna Scott’s character asks audiences to look past the misgivings of her actions and identify with the more relatable aspects of her being. The problem is, that Scott is a rich and famous actress who, at several points throughout the story, struggles to return the affection, decency, and sympathy shown by her love interest, William Thacker (played by Hugh Grant). The role required Julia Roberts to display charm, vulnerability, regret, frustration, love, arrogance, fear, confusion, joy, and anger throughout the 2-hour film. 

The inner complexity that Scott has to contend with often renders her misunderstood. With a cast of loveable characters, an argument can be made that Anna is the least likable. William maintains his good nature throughout the movie and receives unyielding support from his quirky and loving friends. At the end of the day, Scott is, “Just a girl, standing in front of a boy, asking him to love her.”

Notting Hill was another instance in which Julia Roberts had to share the screen with a talented and memorable cast. Her castmates, Hugh Grant, Emma Chambers, and Rhys Ifans, were all nominated by the Blockbuster Entertainment Awards for their respective roles. Roberts was nominated for Best Performance by an Actress in a Motion Picture – Comedy at the Golden Globes, losing to Janet McTeer for her portrayal in Tumbleweeds – a performance that has been all but lost to history.            

2. Erin Brockovich in Erin Brockovich (2000) 

Despite the immense talent of Roberts, she has only won one of her four Academy Award nominations. Her single win was for her remarkable and timeless performance in Erin Brockovich. The role would also see her win Favorite Actress – Drama (Blockbuster Entertainment Awards), Best Performance by an Actress in a Leading Role (BAFTA Awards), Actress of the Year (London Critics Circle Film Awards), Best Actress (Los Angeles Film Critics Association Awards), and Best Female Performance (MTV Movie + TV Awards). 

Aside from Julia’s success, the movie itself would be nominated for Best Picture at the Academy Awards, ultimately losing out to Gladiator (2000). Director Steven Soderbergh won Best Director for the production at the Critics Choice Awards. The film would also help spur the successful and long-standing relationship between Roberts and Soderbergh. Their collaborations extend to a total of five films, including Ocean’s Twelve (2004) and Ocean’s Thirteen (2007).

Erin Brockovich tells the true story of an unemployed single mother becoming a legal assistant who uses her deceptive intelligence and empathetic nature to help take down the California Utility giant Pacific Gas and Electric (PG&E). The company was proven to be responsible for water contamination that led to some form of illness for 634 plaintiffs involved in the historic case. Although the movie wasn’t Robert’s first time undertaking a dramatic role, her portrayal of Brockovich’s story proved the power and extent of her range as an actress. To this day, the role stands out as Julia’s most challenging – requiring grit, emotion, sympathy, and an impressive air.            

1. Vivian Ward in Pretty Woman (1990)

Although the character of Vivian Ward was well within Roberts’ comfort zone, what she was able to do with the iconic role is nothing short of astonishing. Ward is a Hollywood prostitute who takes on a new client, Edward Lewis (played by Richard Gere), who ends up falling for her. Despite Edward being a wealthy and successful businessman, he can’t help but be drawn to Vivian’s carefree, fun, and authentic nature. Of course, Roberts does a masterful job of bringing such a character to life and an argument could be made that the movie comes nowhere near its popularity if the casting was any different. 

Notable actresses also considered for the role were Diane Lane, Molly Ringwald, Michelle Pfeiffer, and Daryl Hannah. Lane was originally tipped for the role but had to decline due to scheduling. Hannah (Wall Street, Kill Bill: Vol. 2) was reported to have turned down the part because she felt the character was demeaning to women. It’s safe to say Hannah likely misunderstood the nuanced nature of Vivian Ward. 

Pretty Woman was directed by Garry Marshall (Runaway Bride, The Princess Diaries) and written by J.F. Lawton (Under Siege). The film won 8 of its 11 award nominations, including Best Performance by an Actress in a Motion Picture – Comedy at the Golden Globes. Roberts would also receive an Academy Award nomination for Best Actress in a Leading Role, ultimately losing to Kathy Bates for her performance in Misery. The production stands as a triumph among romantic comedies and films in general.