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10 of the Most Iconic Drew Barrymore Movies, Ranked

It's impossible to pick our favorites!

Born into an acting family, Drew Barrymore was destined to find fame in the realm of television and movies. Her father was actor John Drew Barrymore, her mother was actress Jaid Barrymore, and each of her paternal grandparents were thespians as well. Furthermore, she’s the goddaughter of Sophia Loren and Steven Spielberg!

Related: Sophia Loren through the years: 18 Rare & Fascinating Photos of Her Life, Love, Legacy

Despite her fame as a young actress, Barrymore had a notoriously troubled childhood, entering rehab by the age of 13 and emancipated from her parents by 14. She made tabloids throughout her teens for her rebellious behavior, but eventually rebranded herself prior to the 2000s, when she started to pivot toward the more wholesome, rom-com sphere.

Drew Barrymore, 1982
Drew Barrymore, 1982Yvonne Hemsey/Getty Images

This new era gave us some of the most celebrated Drew Barrymore movies of her career, her youthful charm shining through in the ingenue roles she was often seen as.

Today, Barrymore has been sober since 2019, has founded her own production company, Flower Films, and hosts the extremely successful daytime talk show, The Drew Barrymore Show.

Related: Drew Barrymore’s Must Have Drugstore Beauty Buys — That You Won’t Be Able To Live Without

Although nearly impossible to narrow down, here, take a look at 10 of the most iconic Drew Barrymore movies of her career!

The 10 most iconic Drew Barrymore movies

10. Charlie’s Angels (2000)

In this modern re-telling of the original 70s series of the same name, Drew Barrymore, Lucy Liu and Cameron Diaz star as Charlie’s Angels, a trio of women that work as private investigators for a mysterious man named Charlie.

In this particular film, the three women work together to recover a stolen voice-recognition system, utilizing their martial arts prowess, charm and good looks to get the job done.

Related: Jaclyn Smith Today: From ‘Charlie’s Angels’ to Style Icon, She’s Still Absolutely Timeless

9. Donnie Darko (2001)

Donnie Darko stars Jake Gyllenhaal as a troubled teenager who sleepwalks outside of his home one night, only to be met with a disturbing figure in a rabbit suit who informs him that the world will end in 28 days.

As the film unfolds, Donnie engages in destructive behavior, facilitated by his seemingly deteriorating mental state and increasing insanity.

Drew Barrymore plays Ms. Pomeroy, his young English teacher who challenges the status quo and doesn’t judge Donnie the way others in his life tend to, as she recognizes the intellect he possesses.

Must-Read: Exclusive Drew Barrymore Interview — How Mental Health, Self-Compassion, and Healthy Foods Have Changed Her Life

8. Never Been Kissed (1999)

Barrymore stars as Josie Geller, a Chicago copy writer, who gets an unexpected opportunity to sharpen her skills as a reporter by going undercover to cover what goes on in the lives of high school students.

Josie, whose actual high school experience was less than stellar, is eager at the opportunity, despite the doubts of those around her. Her initial shot at the story is a bust, as she resorts back to her old, uncool and introverted ways.

However, with the help of her brother, she makes her way into the popular crowd. All the while, she’s falling for her handsome young English teacher.

7. The Wedding Singer (1998) Drew Barrymore movies

Adam Sandler stars in this film as Robbie, a wedding singer, tragically surrounded by love in his profession despite being in the midst of an epic heartbreak.

His profession leads him to Julia (Barrymore), a reception hall waitress, who enlists Robbie to perform as the wedding singer at her own wedding to the slimy Glenn.

Julia convinces Robbie to help her with wedding planning, and as they spend more time with one another, their friendship grows. This love story for the ages has one of the most iconic musical numbers in rom-com history!

6. Ever After: A Cinderella Story (1998)

This fairytale gets reimagined starring Drew Barrymore as Danielle, a young girl who, after the death of her father, is at the mercy of her malevolent step mother, who has forced her to serve she and her two daughters.

However, Danielle’s life takes a turn when she meets Prince Henry, who is trying to escape his arranged marriage. Barrymore stuns in this period piece adaptation.

5. 50 First Dates (2004) Drew Barrymore movies

Drew Barrymore and Adam Sandler reunite once again in 50 First Dates. Sandler plays Henry, a no-commitment bachelor who dates tourists on Oahu, where he works as a vet.

One day he meets Lucy (Drew Barrymore), who piques his interest. However, she was in an accident that resulted in her short-term memory loss, meaning each day, she forgets what happened the day prior.

Henry is committed to making her fall for him over and over, no matter what it takes.

4. E.T. the Extra-Terrestrial (1982)

When an alien makes its way to Earth, it’s discovered by a young boy named Elliott, who, with his brother and little sister Gertie (Drew Barrymore), keep his existence a secret for his safety.

With their new extra-terrestrial friend faced with danger and illness, the siblings will go to great lengths to get him back home safely, even if it means saying goodbye to him for good.

3. Confessions of a Dangerous Mind (2002)

Chuck Barris (Sam Rockwell) is a game show producer who leads a double life — his other being that of a CIA assassin. In this film, Drew Barrymore stars as his girlfriend Penny, who is unaware of this alternate identity.

2. Irreconcilable Differences (1983)

A young Drew Barrymore stars as Casey, a young girl whose parents, one a filmmaker and one a writer, are entirely engrossed in their careers, resulting in Casey spending more time with her nanny than with them.

As a result of this, a young Casey files for emancipation from her parents for their lack of care and total focus on their work.

1. Grey Gardens (2009) Drew Barrymore movies

Grey Gardens is based on the real-life story of a mother-daughter duo, Edith Bouvier “Little Edie” Beale (Drew Barrymore), and mother Edith Ewing “Big Edie” Bouvier (Jessica Lange), who, after their time apart of high society, moved to their Long Island estate.

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As the years went on, the women became more reclusive and the home fell into greater and greater disrepair, overrun with stray animals and garbage.

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