Actress and ’90s icon Drew Barrymore became a box office sensation with memorable movies like Ever After: A Cinderella Story, The Wedding Singer and Never Been Kissed. Barrymore was born into the prominent Barrymore acting family who found originally found fame on the stage before they were solidified as Hollywood royalty by siblings Lionel, Ethel, and Barrymore’s grandfather, John.
She got her first major break appearing inSteven Spielberg‘s film,E.T.: The Extra-Terrestrial,and by the 1990s had taken on dozens of minor roles in popular movies like Batman ForeverandScream.Out of Barrymore’s decades-long career, movie fans rank most of her work as some of the most memorable movies of the 1990s and 2000s, including Charlie’s Angels, Riding in Cars with Boys, and Donnie Darko.
10 ‘Ever After: A Cinderella Story’ (1998)
Danielle (Barrymore) lives as a servant in her own home waiting on her heartless stepmother (Anjelica Huston) and stepsisters, Jacqueline (Melanie Lynskey) and Marguerite (Megan Dodds) but when she disguises herself as a lady of the royal court, she catches the eye of Prince Henry (Dougary Scott) who persistently pursues her. As Danielle and Henry start to fall in love, Danielle realizes that her wicked stepmother has gone to great lengths for Marguerite to marry the prince and will never let them live happily ever after.
Ever After: A Cinderella Story is one of the best modern adaptions of the Brothers Grimm’s famous fairytale. The movie successfully conveys the magic and wonder of the original story through colorful characters and extravagant costumes, including Barrymore’s signature ball gown. Barrymore brings a stubborn charm to the classic character conveying a slightly assertive tone and adding a realistic quality that doesn’t exist in most Cinderella adaptions.
After a kind alien is stranded alone on Earth, he’s discovered by a young boy, Elliott (Henry Thomas), who decides to call him E.T., and with the help of his little sister, Gertie (Barrymore), the kids hide E.T. in their home promising to keep him a secret. E.T. starts to settle into his new home, but when the U.S. government learns of the alien’s existence, Elliott puts his own life at risk and takes drastic measures to save his friend’s life.
During an interview with Ben Mankiewicz on TCM, Spielberg discovered that Barrymore had the perfect imagination for a role like Gertie after she told the director a convincing story about being the lead of a punk rock band. Spielberg admitted that he later realized there was no band, but if Barrymore could believe there was, then she would have no problem believing a mechanical puppet was a real-life alien. In fact, Barrymore was fully convinced that E.T. was real, and years later, her co-star, Thomas, recalled one cold day of filming when Barrymore had asked the wardrobe woman to bring a scarf for E.T.
8 ‘Never Been Kissed’ (1999)
Junior copywriter and late bloomer Josie (Barrymore) is assigned to write about teenage culture and goes undercover as a student at her old high school. Unfortunately, Josie wasn’t exactly prom queen back in the day, but with the help of her brother (David Arquette), she infiltrates the popular group’s inner circle, but her assignment takes a slight turn when she starts to fall for her charming English teacher (Michael Vartan).
Never Been Kissed was Barrymore’s first film produced under her production company, Flower Films, and while it wasn’t a major box office success, the movie has since become a popular cult classic. In 2019, Barrymore posted on her Instagram for the film’s 20th anniversary sharing how she wanted to make a movie that was “raw and ridiculous” and explored what almost everyone experiences one way or another while growing up.
7 ‘The Wedding Singer’ (1998)
Robbie Hart (Adam Sandler) is a great wedding singer who loves his job, but his entire world falls apart when his fiancé leaves him at the altar. After meeting a young woman, Julia (Barrymore), Robbie reluctantly agrees to help her plan her upcoming wedding. As the two start spending time together, Robbie realizes he’s falling in love with her and must stop her from tying the knot.
Before working together, Barrymore had approached Sandler and, according to HuffPost, told him they were “cinematic soulmates.” The actress was onto something, as they had undeniable chemistry in their first movie together, The Wedding Singer, which led to a longtime friendship between the stars. Before filming, Barrymore didn’t read or hear any of the songs, making her reactions more spontaneous. Most of the scenes of Barrymore laughing are genuine, as Sandler often caused her to laugh out of context.
6 ‘Riding in Cars with Boys’ (2001)
In the 1960s, Bev is a typical teen who lives in a small Connecticut town and dreams of becoming a famous writer, but when she’s 15 years old, an unexpected event changes her life, forcing her to put all her hopes and dreams for the future on hold. As Beverly grows into a young woman and mother, she embarks on a difficult but unique journey, bound and determined to do something meaningful with her life.
Riding in Cars with Boys is an underrated coming-of-age movie based on the 1992 memoir by Beverly Donofrio and the last movie directed by Penny Marshall.Barrymore admitted taking on the unsympathetic character of Donofrio was one of the scariest things she’s ever done, but despite the critics’ mixed reviews of her performance, the role proved to audiences that Hollywood’s favorite child star was all grown-up and more than capable of playing complex and dramatic roles.
5 ’50 First Dates’ (2004)
Ladies man and veterinarian Henry Roth (Sandler) lives in Hawaii and is perfectly content with his bachelor lifestyle, but when he meets Lucy, he starts to rethink a committed relationship. As Henry tries to woo Lucy, he discovers that she suffers from short-term memory loss, and despite her family and friends’ disapproval, Henry tries to prove to them that he’s really in it for love and not looking for an easy one-night stand.
After Barrymore read the script for 50 First Dates, she was sold and quickly wrote Sandler a letter telling him that she found their next movie. Even though the movie wasn’t a solid hit with critics, the effortless connection between Barrymore and Sandler in this ridiculous but endearing love story makes it worth watching. Out of all their films, Barrymore and Sandler consider 50 First Dates to be both of their favorite collaborations together.
4 ‘Whip It’ (2009)
Bliss Cavendar (Elliot Page) lives in a small town in Texas and has zero interest in her mother’s obsession with beauty pageants. Wanting to break away from conformity, Bliss ends up joining a roller derby team, the Hurl Girls and keeps her new hobby hidden from her parents, but when a championship game interferes with her upcoming pageant, Bliss’ secret starts to unravel.
Barrymore made her directorial debut with the sports action comedy Whip It, which is an adaptation of the 2007 novel Derby Girl, written by former roller-derby skater Shauna Cross. Whip It has a stellar cast consisting of Barrymore, Juliette Lewis, Kristen Wiig, and Jimmy Fallon and features real roller derby players cast from local teams in Michigan. The movie has its fair share of girl power clichés, but Barrymore and Page’s free-spirited characters and the overall humor and strength of Whip It ranks it as a touchstone female empowerment film.
3 ‘Donnie Darko’ (2001)
Donnie Darko (Jake Gyllenhaal) is a troubled teen who, one night, sleepwalks out of his house and crosses paths with a demonic life-sized rabbit, Frank, who tells him the world will end in 28 days. After the bizarre incident, Donnie starts to experience strange events and continues to have visions of Frank, prompting Donnie to wonder if all of this was just in his head or if he’s possibly living in an alternate universe.
Donnie Darko‘s director and writer, Richard Kelly, had originally met with Barrymore on the set of Charlie’s Angel to discuss the actress playing Donnie’s English teacher, Karen Pomeroy. Barrymore found the script to be “extraordinary” and not only accepted the part but also offered Flower Films to fund the film’s production. While Donnie Darko wasn’t a box office success, it has since become a cult classic and is considered by many movie fans as one of the best modern science-fiction films.
2 ‘Charlie’s Angels’ (2003)
Dylan (Barrymore), Natalie (Cameron Diaz), and Alex (Lucy Liu) are highly trained members of a private detective agency who receive assignments from their unseen boss, Charlie. The women are assigned to rescue Eric Knox (Sam Rockwell), a software genius who has been kidnaped, as well as recover Knox’s revolutionary voice-ID software from a mysterious man dubbed as the “Thin Man” (Crispin Glover).
Charlie’s Angels is a continuationof the hit ’70s television series by the same name, originally starring Kate Jackson, Farrah Fawcett, and Jaclyn Smith, and features John Forsythe reprising his role as the Angels’ millionaire boss, Charlie Townsend.The movie was also another Flower Films production, and its major box office success cemented Barrymore as a promising player in Hollywood both on and off the screen. Barrymore reunited with co-stars Diaz and Liu for a sequel, Charlie’s Angels: Full Throttle.
1 ‘Scream’ (1996)
In the quiet town of Woodsboro, California, high schooler Sidney Prescott (Neve Campbell) and her friends are terrorized by a masked serial killer known as Ghostface. While local law enforcement is baffled by the series of brutal murders, the body count continues to rise, leading Sidney to realize that the killer is someone she knows.
According to Screen Rant, director Wes Craven had wanted to move away from the horror genre and originally passed on directing Scream, but when he heard an established actress like Barrymore had signed on at her request, Craven convinced himself that the movie would be different from his previous work. Barrymore may only have a minor role, but her chilling performance and character archetype became a significant staple in reviving the slasher genre.
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