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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 (2001), Ella Enchanted (2004), Havoc (2005), Brokeback Mountain (2005), The Devil Wears Prada (2006), Becoming Jane (2007), Rachel Getting Married (2008), and Bride Wars (2009). She returned to Mia in 2004's The Princess Diaries 2: Royal Engagement (and is set to reprise the role for a third installment, which was confirmed in November 2022), 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 appearing in films like Interstellar (2014), The Intern (2015), Ocean's 8 (2018), The Witches (2020), Locked Down (2021), and Eileen (2023), as well as the series Modern Love and WeCrashed.

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 (1964), Victor/Victoria (1982), and on The Julie Andrews Hour.

The beloved Sound of Music (1965) 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). She has lent her voice to Shrek 2 (2004), Shrek the Third (2007), Enchanted (2007), Shrek Forever After (2010), Despicable Me (2010) — as well as its 2017 threequel and 2022 spin-off — Aquaman (2018), Bridgerton, and The King's Daughter (2022).

Héctor Elizondo (Joe)

Decades into his career, Héctor 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 the films Born to Win (1971), American Gigolo (1980), The Flamingo Kid (1984), Pretty Woman (1990), and Runaway Bride (1999), and on series Mrs. Cage, Chicago Hope, and Borrowed Hearts.

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), Mother's Day (2016), and Music (2021), as well as episodes of Monk, Grey's Anatomy, Last Man Standing, B Positive, and Star Wars: The Bad Batch.

Heather Matarazzo (Lilly Moscovitz)

A former child star, Heather Matarazzo had already earned '90s credits for Welcome to the Dollhouse (1995), The Adventures of Pete & Pete, Hurricane Streets (1997), Roseanne, The Devil's Advocate (1997), and All I Wanna Do (1998) 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 (2002), Saved! (2004), The Princess Diaries 2: Royal Engagement, Hostel: Part II (2007), and episodes of The L Word, Law & Order, and Exes & Ohs. The actress went on to appear on Grey's Anatomy and in Sisters (2015), Stuck (2018), and Scream (2022).

Mandy Moore (Lana Thomas)

In her first credited onscreen 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 A Walk to Remember (2002), How to Deal (2003), Chasing Liberty (2004), Saved!, Southland Tales (2006), and Because I Said So (2007), as well as voicing Rapunzel in Disney's Tangled (2010) and its spin-off shorts, TV movies, and series. Despite appearing in the films 47 Meters Down (2017), The Darkest Minds (2018) and Midway (2019), Moore has focused more on voice and TV work, playing Rebecca Pearson on This Is Us from 2016 to 2022 and earning other credits for TRON: Uprising, Red Band Society, and Dr. Death.

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 on Gems in the '80s and in 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 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), The Dressmaker (2015), The Crown, Birds of Paradise (2021), and Survive (2022).

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 cofounder took on the gig after previously appearing in a short and playing Paul Baldino in 1999's The Virgin Suicides (his cousin Sofia Coppola's feature directorial debut).

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 small roles, but largely focused on his music, releasing his own solo projects in addition to his work with the band. Schwartzman also directed the indie films Dreamland (2016), The Unicorn (2018), The Argument (2020), and Hung Up on a Dream: The Zombies Documentary (2023).

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 Escape to Witch Mountain (1995), Leave It to Beaver (1997), Brink! (1998), and episodes of Days of Our Lives and 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 onscreen 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).

Patrick John 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 onscreen credit and kicked off his career on a successful note.

The actor spent the early-2000s making one-off appearances on shows like Judging Amy, CSI: Miami, Boston Public, and Grounded for Life before spending three years on CBS' The 4400 as Shawn Farrell (and reprising his role for an episode of the CW reboot in 2022). He went on to appear in Kill Theory and Brothers in 2009 and Footloose in 2011, and stars as Adam Ruzek on Chicago P.D., also popping up in episodes of Chicago Fire from time to time.

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 & 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 the 2010s, 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 from 2011 to 2018. O'Bryan has also appeared on Shameless, Love, Victor, and Kenan, as well as in the films Babylon (2022) and Missing (2023).

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, Oh popped up in Big Fat Liar (2002), Full Frontal (2002), Under the Tuscan Sun (2003), and Sideways (2004), 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 and went on to lead the hit AMC series Killing Eve from 2018 to 2022, also earning credits for Raya and the Last Dragon (2021), Invincible, Turning Red (2022), and Umma (2022).

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 and New Year's Eve (all, like The Princess Diaries, were directed by her father, Gary Marshall).

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 (2003), The Princess Diaries 2: Royal Engagement, Kiss Kiss Bang Bang (2005), For Your Consideration (2006), Get Smart (2008), and Valentine's Day, and episodes of Law & Order, 8 Simple Rules, and Boston Legal. He returned to his 10 Things role of Walter Stratford for the spin-off TV series in 2009. Since then, he's racked credits for NCIS, Mother's Day, and Second Act (2022), among other titles.

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