Actress and ’90s iconDrew Barrymorebecame a box office sensation with memorable movies likeEver After: A Cinderella Story,The Wedding SingerandNever 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 siblingsLionel,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 likeBatman 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, includingCharlie’s Angels,Riding in Cars with Boys, andDonnie Darko.
12’Ever After: A Cinderella Story' (1998)
Appeared as Danielle de Barbarac
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 Afteris one of the best modern adaptionsof theBrothers 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.
Ever After
11’Never Been Kissed' (1999)
Appeared as Josie Geller
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 Kissedwas Barrymore’s first film produced under her production company, Flower Films, andwhile it wasn’t a major box office success, the movie has since become a cult classic. In 2019,Barrymore posted on her Instagramfor 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.
Never Been Kissed
Watch on Roku
10’The Wedding Singer' (1998)
Appeared as Julia Sullivan
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.
Barrymore and Sandler have worked on threemovies, but before working together,Barrymore told him they were"cinematic soulmates." The actress was onto something, asthey 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 made her laugh out of context.
The Wedding Singer
9’Riding in Cars with Boys' (2001)
Appeared as Beverly “Bev” Donofrio
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 Boysis an underrated coming-of-age movie based on the 1992 memoir byBeverly Donofrioand the last movie directed byPenny Marshall.Barrymore admitted taking on the unsympathetic characterof 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.
Rent on Apple TV
8’Everyone Says I Love You' (1996)
Appeared as Skylar Dandridge
Everyone Says I Love Youisan R-rated musical filmdirected byWoody Allen. In the movie, a writer is figuring out how to control his feelings towards a woman he meets in Venice. Meanwhile, his ex-wife and their daughters also try to navigate love and family in New York City. Barrymore plays Skylar Dandridge, one of the writer’s daughters inEveryone Says I Love You.
Barrymore’s undeniable chemistry withEdward Norton’s Holden is charming, cute, and sweet — ultimately elevating the film’s romantic aspect. The movie alsoshowcased Barrymore’s singing and dancing abilities, which further makes her character likable. For fans of Barrymore who want to see her musical side, they should definitely check outEveryone Says I Love You, which has been praised by critics for its strong script and incredible powerhouse cast.
Watch on Fubo
7’Confessions of a Dangerous Mind' (2003)
Appeared as Penny Pacino
George Clooneymade his directorial debut in the movieConfessions of a Dangerous Mind. The movie is based on the autobiography ofChuck Barrisand sees a producer create popular game shows while living a double life as a CIA assassin. However, the truth catches up to him, and he eventually has to deal with the consequences of the crimes that he’s done.
Barrymore plays a supporting role inConfessions of a Dangerous Mindas Penny, who is the girlfriend of the film’s protagonist played bySam Rockwell.Penny as a character is delightful and memorable, as she shows Chuck immense support through the challenges he faces. While there’s a lot to be desired with the film’s pacing and dialogue, viewers will love its original plot and superb acting performances.
Confessions Of A Dangerous Mind
Watch on Pluto
6'50 First Dates' (2004)
Appeared as Lucy Whitmore
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.
AfterBarrymore read the scriptfor Sandler’s50 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, theeffortless connection between Barrymore and Sandler in this ridiculous but endearing love story makes it worth watching. Out of all their films, Barrymore andSandler consider50 First Datesto be both of their favorite collaborations together.
50 First Dates
5’Whip It' (2009)
Appeared as Smashley Simpson
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 thesports action comedyWhip It, which is an adaptation of the 2007 novelDerby Girl, written by former roller-derby skaterShauna Cross.Whip Ithas a stellar cast consisting of Barrymore,Juliette Lewis,Kristen Wiig, andJimmy Fallonand features real roller derby players cast from local teams in Michigan. The movie has its fair share of girl power clichés, butBarrymore and Page’s free-spirited characters and the overall humor and strength ofWhip Itranks it as a touchstone female empowerment film.
Watch on Paramount+
4’Scream' (1996)
Appeared as Casey Becker
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.
DirectorWes Cravenhad wantedto move away from the horror genre and originally passed on directingScream,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 archetypebecame a significant staple in reviving the slasher genre.
3’Donnie Darko' (2001)
Appeared as Karen Pomeroy
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, hadoriginally met with Barrymoreon the set ofCharlie’s Angelsto 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. WhileDonnie Darkowasn’t a box office success, it has since become awidely beloved cult classicand is considered by many movie fans as one of the best modern science-fiction films.
