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Anne Hathaway (Mia Thermopolis)
Anne Hathaway went from plain old Mia Thermopolis to Amelia Mignonette Thermopolis Renaldi, Princess of Genovia, when The Princess Diaries hit theaters in 2001. The actress, who had just one credit to her name with the short-lived Fox series Get Real, made her big-screen debut as the regular high school student whose life changes when she learns her royal lineage. The movie made Hathaway a star, and she spent the 2000s racking up roles in The Other Side of Heaven, Ella Enchanted, Havoc, Brokeback Mountain, The Devil Wears Prada, Becoming Jane, Rachel Getting Married, and Bride Wars. She returned to Mia in 2004's The Princess Diaries 2: Royal Engagement, and went on to book her famed role of Fantine in the 2012 big-screen adaptation of Les Misérables. Hathaway picked up an Oscar, Golden Globe, and a good amount of backlash for the gig, taking a few years off before reappearing in recent years in movies like Interstellar (2014) and The Intern (2015).
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Julie Andrews (Queen Clarisse Renaldi)
Julie Andrews graced The Princess Diaries with her presence as Queen Clarisse Renaldi. By the time she took on the role of Mia's regal grandmother from Genovia, she already had Oscar, Golden Globe, Grammy, and Emmy wins to her name, thanks to appearances in Mary Poppins, Victor Victoria, and The Julie Andrews Hour. The beloved Sound of Music star, who played Queen Clarisse once more in The Princess Diaries 2: Royal Engagement, also popped up in Unconditional Love (2002), Eloise at the Plaza (2003), and Tooth Fairy (2010), and lent her voice to Shrek 2 (2004), Shrek the Third (2007), Enchanted (2007), Shrek Forever After (2010), and Despicable Me (2010).
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Hector Elizondo (Joe)
Decades into his career, Hector Elizondo joined The Princess Diaries as Joe, the security guard for the Queen who ends up bonding with Mia. His previous credits included turns in Born to Win (1971), American Gigolo (1980), The Flamingo Kid (1984), Pretty Woman (1990), Mrs. Cage, Chicago Hope, Borrowed Hearts, and Runaway Bride (1999). After playing Joe both in the 2001 film and its 2004 sequel, Elizondo continued to add to his résumé with Georgia Rule (2007), Love in the Time of Cholera (2007), Valentine's Day (2010), New Year's Eve (2011), as well as episodes of Monk, Grey's Anatomy, and Last Man Standing.
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Heather Matarazzo (Lilly Moscovitz)
A former child star, Heather Matarazzo had already earned '90s credits for Welcome to the Dollhouse, The Adventures of Pete & Pete, Hurricane Streets, Roseanne, The Devil's Advocate, and All I Wanna Do when she signed on to play Lilly Moscovitz. She was Mia's confidant and support system as her best friend, going through the transition to royalty with her — though sometimes less enthusiastically than others. Matarazzo spent the 2000s popping up in titles like Sorority Boys, Saved!, The Princess Diaries 2: Royal Engagement, Hostel: Part II, and episodes of The L Word, Law & Order, and Exes and Ohs. In recent years, she cameoed on Grey's Anatomy and had a small role in 2015's Sisters.
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Mandy Moore (Lana Thomas)
In her first credited on-screen feature film role, Mandy Moore played Lana Thomas, the leader of the popular cheerleader clique. Along with carbon-copy BFFs, Lana torments Mia as she threatens the girls' social standing. Before playing the high school student, Moore earned a voice role in 2001's Dr. Dolittle 2 and made a name for herself with her pop career, which included hits like "Candy," "I Wanna Be with You," and "In My Pocket." After The Princess Diaries, she continued to act, appearing in How to Deal (2003), Chasing Liberty (2004), Saved! (2004), Southland Tales (2006), and Because I Said So (2007). In recent years, Moore focused on voice and TV work, earning credits for Tangled, TRON: Uprising, and Red Band Society.
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Caroline Goodall (Helen Thermopolis)
Caroline Goodall was the voice of reason in The Princess Diaries as Helen Thermopolis, Mia's even-keeled cool mom. The actress came into the role after making previous appearances in Gems in the '80s, Every Time We Say Goodbye (1986), Hook (1991), Cliffhanger (1993), Schindler's List (1993), and Disclosure (1994). After playing Helen, Gooddall reunited with Moore in 2004's Chasing Liberty and returned for The Princess Diaries 2: Royal Engagement. She went on earn credits for Haven (2004), My Life in Ruins (2009), Dorian Gray (2009), The Cold Light of Day (2012), Third Person (2013), Nymphomaniac: Vol. II (2013), The Best of Me (2014), and The Dressmaker (2015).
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Robert Schwartzman (Michael Moscovitz)
Robert Schwartzman charmed in The Princess Diaries as Michael Moscovitz, Lilly's shy hipster older brother, who plays in a band and has a crush on Mia. The Rooney co-founder took on the gig after previously appearing in a short and playing Paul Baldino in 1999's The Virgin Suicides. In the years since, Schwartzman continued to record with Rooney's various iterations, but Princess Diaries was his last major film role. He popped up in various shorts and unnamed roles, but largely focused on his music, releasing his own solo projects in addition to his work with the band.
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Erik von Detten (Josh Bryant)
The ultimate millennium heartthrob, Erik von Detten played Josh Bryant, the school's resident popular hottie. In one of the movie's tenser moments, Josh asks Mia to the big dance, only to give her a disaster of an evening. A former child star and Disney alum, von Detten took on the role after appearing in Days of Our Lives (1993), Escape to Witch Mountain (1995), Leave It to Beaver (1997), Brink! (1998), and episodes of So Weird. In the years since his turn as Josh, von Detten earned TV credits for Raising Dad, The Legend of Tarzan, Law & Order: Special Victims Unit, Charmed, Dinotopia, Complete Savages, and Malcolm in the Middle. While he hasn't appeared in recent years, he popped up in a 2008 episode of Bones, lent his voice to a 2009 episode of Family Guy and returned to his character Sid for a small voice role in Toy Story 3 (2010).
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Patrick Flueger (Jeremiah Hart )
Patrick John Flueger rocked some serious hair dye to play Jeremiah Hart in The Princess Diaries, an alternative-leaning friend of Mia and Lilly's. The role was Flueger's first on-screen credit and kicked off his career on a successful note. The actor spent the early 2000s making one-off appearances in shows like Judging Amy, CSI: Miami, Boston Public, and Grounded for Life before spending three years on CBS' The 4400 as Shawn Farrell. He went on to appear in Kill Theory and Brothers in 2009 and Footloose in 2011, and currently stars as Adam Ruzek in Chicago P.D., also popping up in episodes of Chicago Fire from time to time.
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Sean O’Bryan (Mr. O'Connell)
Sean O’Bryan played Mr. O'Connell in The Princess Diaries, Mia's debate teacher, who ends up eyeing a relationship with her mother. Before taking on the role of Patrick O'Connell, O'Bryan filled his résumé with appearances in Frankie and Johnny (1991), Chaplin (1992), Heart and Souls (1993), and Phenomenon (1996), and episodes of MacGyver, Northern Exposure, Beverly Hills, 90210, Murder, She Wrote, Chicago Hope, and Brother's Keeper. O'Bryan returned to Princess Diaries for its 2004 sequel, also earning credits for Raising Helen (2004), a 2005 stint on Six Feet Under, Mission: Impossible III (2006), Vantage Point (2008), and Yes Man (2008). In recent years, he hit the big screen in New Year's Eve (2011), Olympus Has Fallen (2013), London Has Fallen (2016), and Mother's Day (2016), and played Ron Donahue on The Middle.
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Sandra Oh (Vice Principal Gupta)
Sandra Oh led Mia's school as Vice Principal Gupta, an administrator with a particular affection for royalty. She came into the gig after making previous appearances in Bean (1997), Last Night (1998), and Waking the Dead (2000), and spending years playing Rita Wu on HBO's Arliss. In the early 2000s, she popped up in Big Fat Liar, Full Frontal, Under the Tuscan Sun, and Sideways, and episodes of The Proud Family, before booking her most famous role to date as Dr. Cristina Yang on Grey's Anatomy. She spent nearly nine years on Grey's, also earning credits for The Night Listener (2006), For Your Consideration (2006), Defendor (2009), Ramona and Beezus (2010), and Rabbit Hole (2010) during that time. Oh wrapped her run as Cristina in 2014.
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Kathleen Marshall (Charlotte Kutaway)
Kathleen Marshall picked up a gig as Charlotte Kutaway in The Princess Diaries, playing the secretary to Andrews' Queen Clarisse. Marshall's pre-Princess credits include a late '70s run on Happy Days, small roles in The Flamingo Kid (1984), Nothing in Common (1986), Beaches (1988), and Pretty Woman (1990), and appearances in A League of Their Own (1992), Exit to Eden (1994), Freeway (1996), Edtv (1999), Never Been Kissed (1999), and Runaway Bride (1999). After hitting the big screen in Raising Helen (2004), Marshall returned to Charlotte for The Princess Diaries 2: Royal Engagement, and went on to earn credits for Valentine's Day (2010) and New Year's Eve (2011).
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Larry Miller (Paolo)
Larry Miller had a hilarious turn in The Princess Diaries as Paolo, the hairstylist whom Queen Clarisse brings in to give Mia a makeover. He eventually blows the Princess' cover, but he does make her look fabulous. Prior to the gig, Miller earned credits for Three Fugitives (1989), Pretty Woman (1990), L.A. Story (1991), Undercover Blues (1993), Dream On, The Nutty Professor (1996), Waiting for Guffman (1996), Life's Work, Mad About You, 10 Things I Hate About You (1999), Best in Show (2000) and Dilbert. After playing Paolo, Miller appeared in A Mighty Wind, Law & Order, 8 Simple Rules, The Princess Diaries 2: Royal Engagement , Kiss Kiss Bang Bang, For Your Consideration, Get Smart Boston Legal, and Valentine's Day. He returned to his 10 Things role of Walter Stratford for the spin-off TV series in 2009.