In 1998, Adam Sandler and Drew Barrymore made their first film collaboration starring in The Wedding Singer, Frank Coraci’s rom-com following Robbie Hart, a broken-hearted wedding singer who falls in love with a waitress. The chemistry between these two stars completely transcended the screen so, a few years later, they got back together and starred in a new rom-com: 50 First Dates. This 2004 film directed by Peter Segal follows Henry Roth, a womanizing marine veterinarian with little intention of settling down and committing to a woman. That all changes when he meets Lucy, a young local girl who sweeps him off his feet, but things may not be as straightforward as he thinks, because she suffers from anterograde amnesia due to a car accident, and every time she goes to sleep, she loses track of her new experiences. However, Henry’s feelings for her drive him to accomplish a tough task: making her fall in love with him every single day.
This Sandler and Barrymore rom-com was met with mixed reviews praising the chemistry between the leads but criticizing the production’s overall humor. It also became a box-office hit that prompted remakes in Mexico, Japan, India and Iran. The cast of this film went on to star in many popular projects over the years, most notably Sandler and Barrymore. In fact, many of the actors involved in 50 First Dates went on to work with Sandler again in several movies produced by his company, Happy Madison. Here’s a look at the current projects of this popular rom-com’s cast.
Adam Sandler
Several years before starring in 50 First Dates as Marine vet Henry Roth, Adam Sandler was already leading popular hits such as Billy Madison, Happy Gilmore and Big Daddy. Over the years, he kept starring in and producing comedy films, such as You Don’t Mess with the Zohan and Just Go With It, among many others. Still, he eventually wowed audiences and critics alike by striking out in something that seemed totally out of his comfort zone: dramatic roles.
In 2019, Sandler starred in Uncut Gems, a crime thriller directed by the Safdie brothers that earned him critical acclaim. A few years later, such recognition intensified with his role in Hustle, a production that proved Sandler can tackle any kind of role. 2023 is expected to be a big year for the actor, as he will be featured in several productions. Among them, the most long-awaited are Murder Mystery 2, sequel to the 2019 film he starred in with Jennifer Aniston, Spaceman, and Leo, an animated movie in which he will portray Leo, the pet lizard of an elementary school class. Additionally, Sandler is producing The Out-Laws, a crime comedy film starring Adam DeVine and Pierce Brosnan.
Drew Barrymore
Drew Barrymore‘s story is quite similar to Sandler’s: before playing Lucy Whitmore in the 2004 rom-com, the actress was world-famous for several productions, including the 1982 film E.T. the Extra-Terrestrial. After starring in 50 First Dates, Barrymore continued to appear in films that made her one of the industry’s biggest stars, and she even ventured into directing with the 2009 movie Whip It.
In recent years, Barrymore was involved in a few film projects, such as The Stand In and A Castle for Christmas. However, in 2021, she announced that she would be taking an indefinite break from acting, and focused on one of the greatest projects of her career: her daytime talk show The Drew Barrymore Show, which has been renewed for a fourth season this past January.
Rob Schneider
Rob Schneider started his career as a stand-up comedian and eventually established himself as a performer on Saturday Night Live. Over the years, he appeared in several comedy films and even directed a few of them, making his directorial debut in 2007 with Big Stan. Schneider also worked with Sandler on a number of his projects, including Grown Ups, Hubie Halloween, and Home Team, the 2022 film starring Kevin James and produced by Sandler.
In 2021, Schneider was a contestant on the sixth season of The Masked Singer, where he was unmasked during the fifth week of the show. His latest project so far is the film Daddy Daughter Trip, starring, directed, and produced by himself. It features performances by his wife and one of his daughters. In 50 First Dates, Schneider plays Ula, Henry Roth’s friend and assistant.
Sean Astin
By the time Sean Astin played Doug Whitmore in 50 First Dates, he was already world-famous for one of the most important roles of his career: Samwise Gamgee, better known as Sam, in the Lord of the Rings trilogy. Over the years, Astin has been featured in a number of films and shows, and he even voiced animated characters in productions such as Justice League: War and the Teenage Mutant Ninja Turtles TV series.
In 2017, he became even more popular thanks to his involvement in the Netflix hit Stranger Things, where he played Bob Newby, and in recent years he has made cameos in other popular series, such as The Big Bang Theory, Supergirl, and Brooklyn Nine-Nine. Currently, Astin is working on the upcoming film Cash Out, where he is set to co-star alongside John Travolta, Kristin Davis and Quavo and Lukas Haas.
Blake Clark
In 50 First Dates, Blake Clark plays Marlin Whitmore, Lucy’s father. However, he is also well known for voicing a very popular animated character: Slinky Dog from the Toy Story franchise. Clark assumed the role after the original actor, Jim Varney, passed away in 2000, and has played the character from 2008 onward. He is another one of Sandler’s frequent collaborators, and after the 2004 rom-com he was cast alongside him again in movies such as I Now Pronounce You Chuck & Larry, Bedtime Stories, and Grown Ups. His latest project to date was the sitcom United States of Al, a production that ran for two seasons before getting canceled last year.
Dan Aykroyd
Actor Dan Aykroyd was also extremely popular before joining Sandler and Barrymore’s rom-com: in 1984 he rose to fame playing Ray Stantz in Ghostbusters, a role he has continued to play throughout several films in the franchise. Over the years, Aykroyd also stepped in as an executive producer, working on the 2016 reboot Ghostbusters and Ghostbusters: Afterlife. Throughout his career, the actor excelled in films and TV productions of all genres. His latest projects so far were the 2017 sitcom Workin’ Moms and the 2020 show Paranormal Hotel. In 50 First Dates, Aykroyd plays Dr. Joseph Keats, Lucy Whitmore’s doctor.
Amy Hill
The role of Sue, the Hukilau café manager in 50 First Dates is, to this day, one of the most memorable in Amy Hill‘s career. However, this comedian and actress has been featured in a number of hit productions over the years, including the films Lilo & Stitch and Spider-Man: Homecoming, as well as the TV shows That’s So Raven, Two and a Half Men and American Dad! Since 2018, Hill has played Kumu in the TV series Magnum P.I., which premiered its fifth season last February. Her latest film production so far was Katie Aselton’s comedy Mack & Rita, where she co-starred with Diane Keaton, Elizabeth Lail, Taylour Paige and Loretta Devine.
Allen Covert
In 50 First Dates, Allen Covert plays a minor but unforgettable role as Ten Second Tom, a man with a condition that makes him lose his memory every ten seconds. This artist has worked with Sandler in a great number of films, either as an actor, producer, or writer. He is also part of his production company, Happy Madison Productions. Among the most memorable films in which he has appeared are Happy Gilmore, Big Daddy and Just Go With It, among many others. In recent years, Covert has been involved in movies such as The Wrong Missy, Hubie Halloween, and Home Team. He was also a member of the production team for the upcoming movie Murder Mystery 2.
Missi Pyle
Actress and singer Missi Pyle is known for multiple film roles, though probably one of the most notable is as Mrs. Beauregarde in the 2005 film Charlie and the Chocolate Factory. Throughout her career, Pyle has been featured in blockbuster projects such as the films Big Fish, The Artist and Gone Girl and the shows Impulse and Dirty John.
2022 was a busy year for the actress, who landed parts in the productions Mr. Mayor, Y: The Last Man, A Tale Dark & Grimm and Star Trek: Lower Decks. She is also expected to star in Netflix’s upcoming rom-com A Tourist’s Guide to Love, alongside Rachael Leigh Cook, Scott Ly and Ben Feldman. In 50 First Dates, Pyle makes a small cameo as Noreen, a young woman Henry goes on a date with.
Maya Rudolph
Many people don’t remember seeing Maya Rudolph in 50 First Dates, and it’s probably because her role in the rom-com was pretty minor: she played Stacy, a friend of Lucy Whitmore. Over the years, Rudolph grew into a popular Hollywood figure, and was featured in major projects such as Bridesmaids, Wine Country and A Prairie Home Companion, among many others. She has also lent her voice to many animated films, including The Mitchells vs. the Machines and Luca, two of the biggest hits of recent years.
In late-2022, Rudolph starred alongside Amy Adams and Patrick Dempsey in Disenchanted, the sequel to the 2007 film Enchanted. In it, she portrayed Malvina Monroe, the main antagonist of the story. That same year, she was added to the cast of the adult animated show Human Resources, voicing Connie, a role she has been playing in Big Mouth since 2017. This year, she is expected to star in the upcoming animated film Teenage Mutant Ninja Turtles: Mutant Mayhem directed by Jeff Rowe.
