Drew Barrymore is one of the most versatile actors out there due to the many different roles she has played over the years. She comes from a family of celebrities, so it's no wonder where she has gotten her talent from. Barrymore’s talent enabled her to start acting at such a young age, and she didn't disappoint anyone who bet on her. She appeared in many iconic films like Scream and E.T. the Extra-Terrestrial which increased her popularity between the audience and critics.
Another thing that made Barrymore who she is today is that her life wasn't always easy. Her parents’ divorce played a role in the development of her character, and it deeply affected her. What's admirable is that she didn't give up back then and instead, she became someone who fights back.
Today, we would see Barrymore in her talk show which has brought a lot of controversy lately because she decided to continue her talk show during the strikes. However, she decided against that after listening to everyone. Now that things are starting to calm down, we can focus on Barrymore’s talent. Here are her best 2000s movies, ranked.
10 He’s Just Not That Into You
He’s Just Not That Into You was one of Barrymore’s famous films and it was directed by Ken Kwapis and released in 2009. The film was based on a self-help book under the same name which was written by Greg Behrendt and Liz Tuccillo. We get to see several stories taking place in the film and each one of them tells us how relationships are complicated. Despite the good idea that the film had, some criticized it due to how the stories were short which made it difficult to connect with the characters of any of these stories.
In He’s Just Not That Into You, we see Barrymore’s character, Mary Harris, as she struggles with online dating. The film discusses how people misunderstand each other in relationships and it does so through these various relationships we get to look at between this group of friends. While Barrymore didn't have that much screen time, her performance is still memorable.
9 Riding in Cars with Boys
Riding in Cars with Boys was directed by Penny Marshall, and it was released in 2001. It is based on a memoir by Beverly Donofrio. In the film, Barrymore plays the role of a young woman, Beverly Donofrio, who dreams of going to New York in the hope of becoming a writer. However, her dream isn't as easy as she would like it to be since she faces many unexpected events like unplanned teen pregnancy at the age of 16.
The film found some success which is probably thanks to Barrymore. It still received criticism from critics while others did enjoy it because of its heart-wrenching story. We see how Donofrio deals with addiction, an unexpected child, and more in the film. There is no denying that the role was complex, but Barrymore was up to the task.
8 Charlie’s Angels
Charlie’s Angels, the 2000 film, is one of Barrymore’s most famous works even after more than 20 years. The film was a remake of the TV series under the same name, and it was a successful one. The film was led by the amazing three females Barrymore, Cameron Diaz, and Lucy Liu who proved that women can make a successful action movie in the lead roles. The success of the film led to a sequel which is titled Charlie’s Angels: Full Throttle.
The three of them are the best agents out there as they are supervised by Bosley (Bill Murray). They go on a mission to locate a kidnapped developer, and it is no easy task. Their confidence was apparent to the audience and it played a role in the huge success of the film at the box office. Charlie’s Angels will always remain part of film history and one of Barrymore’s best films. No one can forget about Dylan, the rebellious character who is a romantic at heart.
7 Music and Lyrics
Music and Lyrics is a romantic comedy film that was released in 2007 and directed by Marc Lawrence. The film follows a former musical superstar named Alex Fletcher (Hugh Grant) who doesn't have the same talent or audience as before. Things start to change when the young and famous singer Cora Corman (Haley Bennett) asks Alex to write a song for her. The only problem is that he hasn't written a song for many years and finds it difficult to do so now.
This is when Barrymore comes in. Playing the role of Sophie, Barrymore is a gift sent from heaven to Alex who realizes that Sophie can help him write songs since she has the talent. As a rom-com, it was normal to see the two of them, Alex and Sophie, fall in love. Yet, the film also had a deeper message about the idea of making art and creatives losing their confidence that then returns to them when they work together. The chemistry between Barrymore and Grant is enough to make you watch the film.
6 Whip It
Whip It, which was released in 2009, is one of Barrymore’s most successful films. It also marked her directorial debut. Whip It is a sports comedy film that follows a group of roller derby girls in Texas. We see Elliot Page playing the role of Bliss Cavender, a teenager who just discovered that a roller derby league exists nearby and decides to try it out under the name of Babe Ruthless. We see how Bliss becomes part of this roller derby group which helps Bliss’ confidence grow.
The film was based on a novel titled Derby Girl which was written by Shauna Cross. Whip It was a great directorial debut for Barrymore as she did a great job directing her first movie. The film found more success with critics than it did with the audience, but it is still a good film that deserves a watch.
5 Fever Pitch
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Fever Pitch was released in 2005 and it was based on a book under the same name written by Nick Hornby. What might come as a surprise is the fact that Barrymore had Jimmy Fallon starring in the film with her. The Tonight Show host turned out to be good at acting just like he is good at making us laugh. The romantic comedy film follows a Boston Red Sox fan named Ben Wrightman (Fallon) as he falls in love with a workaholic woman, Lindsay Meeks (Barrymore).
It's romantic and all until the Boston Red Sox reaches the playoffs, and Ben’s extreme love for the game and his team starts to show. This complicates their relationship as he seems to care more about baseball than he cares about Lindsay. Fever Pitch is a film about compromise and dealing with your partner’s fanaticism when it comes to a hobby or something they love. While the team’s fans didn't enjoy the film as much as its creators hoped, the film still found success with the audience.
4 50 First Dates
50 First Dates is a romantic comedy film that was directed by Peter Segal and released in 2004. It follows Henry Roth (Adam Sandler), a marine veterinarian, when he meets and falls in love with Lucy Whitmore (Drew Barrymore). The only problem that comes between them is the fact that Lucy suffers from short-term memory loss which makes her incapable of remembering anything that took place the day before. However, Henry isn't ready to let that stop him from getting Lucy to like him. After all, she was the one who made him overcome his fear of commitment.
Henry tries his best to make Lucy like him every single day which proves that he is willing to commit to her. 50 First Dates has a heartwarming story that you can't help but love, and while it didn't find that much success with critics, it was successful at the box office. It also proved that the chemistry between Barrymore and Sandler will always make their films together successful.
3 Confessions of a Dangerous Mind
Confessions of a Dangerous Mind was released in 2002 and it was George Clooney's directorial debut. The film was based on Chuck Barris's 1984 unauthorized biography which detailed how he insisted that he led a double life for years as a CIA hitman and killed over 30 people. The game show host’s character was played by Sam Rockwell who did more than a great job. In Confessions of a Dangerous Mind, Barrymore plays the role of Penny, Chuck’s girlfriend. Despite his weird behavior, refusal to get married, and cheating on her, Penny stays with Chuck.
The film is quite interesting especially as it leaves you questioning Chuck’s claims and whether they are true or simply fiction. In the end, he does marry Penny who questions his words about him being an assassin for the CIA. Shifting from comedy to thriller, Confessions of a Dangerous Mind was a successful movie and was also praised by critics. Barrymore’s performance was amazing as usual and her chemistry with Rockwell played a role in the film’s success.
2 Grey Gardens
Grey Gardens was released in 2009 and directed by Michael Sucsy. It is about the true story of the lives of Edith Ewing Bouvier or big Edie (Jessica Lange) and her daughter Edith Bouvier Beale or little Edie (Barrymore). The two of them were Jacqueline Kennedy’s aunt and cousin. It is a story about a complicated family and Lange and Barrymore didn't disappoint us in delivering a great performance. We see how their life declined as they now lived in a decaying mansion.
The film was based on a 1975 documentary under the same name. While Grey Gardens is one of Barrymore’s lesser-known films, it was very successful when it was first released. It even became a cult classic as it also won many awards. Not to mention that it gave Barrymore her first Golden Globe Award which is enough to love the film even more. So it comes as no surprise that the film is one of Barrymore’s highest-rated works.
1 Donnie Darko
Donnie Darko is a bizarre sci-fi film that was directed by Richard Kelly and released in 2001. It follows Donnie (Jake Gyllenhaal) who is going to have a bizarre accident, one where a jet engine lands through his house, only to escape it at the last moment because he was sleepwalking. After this, he starts seeing a mysterious figure who is wearing a rabbit costume and is named Frank (James Duval). Frank informs him that the world will end in 28 days. These weird events don’t stop here as the rabbit figure also manipulates Donnie and makes him commit several crimes.
On the other hand, Barrymore’s role in Donnie Darko was a small one as we see her playing the role of an English teacher named Karen Pomeroy. Despite that, her character and performance are still memorable. Plus, we can't ignore that she was a firm believer in the film, and its capability to find success with the audience which led to her company, Flower Films, producing it. Now, Donnie Darko has become one of Barrymore’s best films and it certainly deserves that title.
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