Drew Barrymore and Adam Sandler have starred in three movies together, one in each decade and hinting at a fourth pairing soon. Are we ready to see this dynamic duo reunite on our screen again?
The journey to bring the two actors together was a chaotic one. Drew Barrymore described in the 2016 memoir, Wildflower that though she had acted in several films prior, Drew had to ‘beg, borrow and steal‘ to get Adam Sandler to meet her in person. From that moment began the series of blockbusters of the iconic duo we adore today.
These movies have not just unraveled the electric chemistry between the two but accelerated Sandler’s career and placed him on the map as a comic sensation. Following the release of these films, he credited Barrymore with getting him lead roles in romantic movies.
Let’s take a walk down the past three decades and relive their iconic collaborations.
List of Adam Sandler and Drew Barrymore’s Movies:
1. The Wedding Singer (1998)

- Director: Frank Coraci
- Writer: Tim Herlihy
- IMDb Rating: 6.9/10
- Streaming Platform: Netflix
One of the top movies to hit the theatre, The Wedding Singer, a romantic comedy, was considered one of the best performances in the career of Sandler and Barrymore.
The Wedding Singer Plot:
After being stranded at the altar, Robbie Hart, played by Sandler, has to return to his work. He works as a wedding singer, which is one of the world’s most romantic careers. A hilarious portrayal of Robbie’s depression post being left at the altar, things change when he meets Julia Sullivan, played by Barrymore.
The Wedding Singer Review:
The movie depicts the two characters falling in love in a way that seems so organic and not forced, and it just adds to the essence of the film. It is a charming love story that will make you fall in love with the duo and set the trend for forthcoming iconic collaborations. The movie and its classic 80’s fashion, incredibly hilarious depictions, and music make this film a major box office hit and a must-watch.
If I see The Wedding Singer playing on TV, I can’t turn away. I’m fatalistically stuck. @AdamSandler @DrewBarrymore
— Gad Saad (@GadSaad) February 9, 2022
2. 50 First Dates (2004)

- Director: Peter Segal
- Writer: George Wing
- IMDb Rating: 6.8/10
- Streaming Platform: Amazon Prime
A love story based on real-life, it revolves around a veterinarian (Adam Sandler) who falls in love with a woman that undergoes daily memory loss (Drew Barrymore). This movie is based on the story of Michelle Philpots, who suffered two head injuries. A light romantic comedy that brings out the raw on-screen chemistry between Adam Sandler and Drew Barrymore through their coy sincerity and tone of expression.
50 First Dates Plot:
Henry Roth, a marine biologist (Sandler), falls in love with Lucy (Barrymore). But soon realizes that her memory of him is lost every night. Lucy’s loving father and the staff at the local diner are dubious about the intentions of Henry. But Henry claims he is so in love with her that he is willing to start over with Lucy every morning.
50 First Dates Review:
This movie was not popular among the critics and raised questions about its ethical issues. Because 50 First Dates were meant to be a movie that is not too deep and remains an entertaining watch.
The movie exposes a warm and gentler Adam Sandler, away from his usual anger and gross-out humor, and his character throughout the film is honestly attractive. 50 First Dates is a lovable and surprisingly emotional movie that plays out very well.
3. Blended (2014)

- Director: Frank Coraci
- Writer: Clare Sera, Ivan Menchell
- IMDb Rating: 6.5/10
After two successful box office films, Sandler and Barrymore reunited for a third movie directed by Frank Coraci.
Blended Plot:
After a bad blind date, Jim (Adam Sandler), Lauren (Drew Barrymore), and their respective families get stuck together in one suite at an African resort. However, an unfortunate circumstance turns into an action-packed movie. Then the duo falls in love and realizes there is potential for a relationship.
Blended Review:
The movie received a lot of criticism and was also called an awkward whiff. Then too the movie saw some great acting by Adam Sandler and Drew Barrymore. The duo’s easy chemistry, tonal consistency, and well-scouted locations make the film worth a one-time see.
#DrewBarrymore and #AdamSandler in The Wedding Singer (1998), 50 First Dates (2004) and Blended (2014) pic.twitter.com/Esh9ga9TQ8
— IMDb (@IMDb) March 2, 2020
What’s Next?
A fourth film in the making?
Amidst the Coronavirus pandemic, Sandler and Barrymore caught up virtually as they accepted the GOAT Dynamic Duo honor at the 2020 MTV Movies & TV Shows: Greatest of All Time. Succeeding three romantic comedies released in each decade, the frequent collaborators tease at a possible fourth movie together in this new decade.
It takes two to receive the Dynamic Duo honor at the #MTVAwards: Greatest of All Time! 🍿
CONGRATS @AdamSandler and @DrewBarrymore! 💕✌️ pic.twitter.com/q4FLvc0pQM
— MTV (@MTV) December 7, 2020
Their fun bond and affection for each other leave the fans excited at the hint of a new film. As for when the next collaboration could be, it lies in the hands of only Adam Sandler and Drew Barrymore.
Will this possible upcoming film be a bigger hit than the last three?
And will it match up to the incredible hype this duo has built over the years?
Guess we will have to wait and see.
What Drew Barrymore and Adam Sandler’s Relationship Looks Like?

A chaotic beginning that was not easy, the two have grown to become one of Hollywood’s best-seen on-screen couples. Over the years, their friendship has accelerated, and they share a genuine love for each other. While fans have often wondered whether they ever shared romantic feelings, their curiosity was curbed by Chelsea Handler in a 2014 interview.
The truth could break some people’s hearts – Sandler and Barrymore have always remained platonic friends. When they are not making films or greeting each other at award ceremonies, the two close friends keep in touch when they can.
The best part about their friendship is that Sandler’s wife loves Drew. In fact, she is the one who encourages Adam through a nice romantic scene; Jackie truly is their little hype girl.
Where are They now?
It sounds like the perfect friendship, a rocky beginning that transformed into chemistry and a bond like no other. From Wedding Singer to Blended, this couple has taken Hollywood’s romantic comedies through a storm.
Sandler appeared as the first guest on Barrymore’s talk show, The Drew Barrymore Show. Then, in a comedy segment, the two reprised their roles on 50 First Dates, portraying how the characters could be doing during the testing pandemic year of 2020.
Recently, Drew was invited to present the Best Actor Award to Adam Sandler for his performance in Uncut Gems (2019) during the National Board of Review Annual Awards Gala in January 2020. The two had a lovely and emotional exchange.
An unexpected pairing with immense chemistry. Drew always knew she and Sandler were meant to be, and it was no secret that she was absolutely right.
Astonishing Facts about Drew and Adam:
- Drew wants to make movies with Adam forever.
- Jackie Sandler, Adam’s wife loves Drew.
- Drew’s book has a chapter Love Letter, for Adam.
- Adam and Drew have never dated.
- Adam and Drew sang on The Tonight Show, starring Jimmy Fallon.
- Drew was invited to present the Best Actor Award to Adam Sandler.
- Drew had to ‘beg, borrow and steal‘ to get Adam Sandler to meet her in person.
- Drew says, “every 10 years we get to fall in love again” and they both enjoy it.