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Drew Barrymore as Julia Sullivan
With the days of portraying sweet, conflicted waitress Julia Sullivan long behind her, Drew Barrymore has stayed a massive presence in Hollywood. Shortly after the success of The Wedding Singer, she went on to star in Ever After: A Cinderella Story (1998), Never Been Kissed (1999) and Charlie's Angels: Full Throttle (2000). Barrymore even reunited with Adam Sandler for two more films, 50 First Dates (2004) and Blended (2014).
She scored an Emmy nomination and Golden Globe win for lead actress in a miniseries or a movie for her performance in the 2009 HBO biopic Grey Gardens. Barrymore made her directorial debut with the sports dramedy Whip It later that year.
The actress launched her eponymous daytime talk show, The Drew Barrymore Show, in September 2020. Variety reported in January 2023 that CBS announced its renewal through 2024.
Barrymore has also kept busy off-screen. In 2021, she released her first cookbook, Rebel Homemaker, with chef Pilar Valdes and a lifestyle magazine, Drew Magazine. She also launched Flower Beauty and Flower Home with Walmart for her Beautiful Kitchenware line.
Barrymore has two daughters, Olive and Frankie, with ex-husband Will Kopelman, who she divorced in August 2016 after four years of marriage. Without naming names, Barrymore told Whoopi Goldberg in 2022 she was back on the dating scene.
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Adam Sandler as Robbie Hart
Sandler has been a comic mainstay since the mid-'90s, and the actor/screenwriter/producer's career only blossomed following his role as good-natured crooner Robbie Hart, who only wants to grow old with you.
He is known for comedies like Big Daddy (1999), Longest Yard (2005), Click (2006) and Grown Ups (2010). In 2002, however, with his role in Punch Drunk Love, Sandler proved his chops as an actor beyond the scope of his typically goofy parts. This trend continued with him being cast in Noah Baumbach's The Meyerowitz Stories (2017) and 2019's Safdi brothers' crime thriller Uncut Gems — a performance met with critical acclaim.
In 2020, Netflix announced a four-movie deal with Sandler's production company, Happy Madison Productions, which kicked off with Hubie Halloween (2020). In 2023, it was announced that Sandler and Jennifer Aniston were teaming up for a sequel to their wildly popular Murder Mystery (2019).
Sandler and his wife Jacqueline have been married since 2003 and share two daughters, Sadie and Sunny.
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Christine Taylor as Holly Sullivan
After playing Julia's intuitive cousin and BFF, Holly, Christine Taylor continued her trend of appearing in popular comedies like Zoolander (2001), Dodgeball (2004) and Tropic Thunder (2008), as well as enjoying stints on TV shows like Arrested Development and Search Party. In 2020, it was announced that the actress would be joining the cast of Apple TV+'s comedy series, High Desert, created by Patricia Arquette and Ben Stiller.
Taylor and Stiller married in 2000 and announced their separation in 2017. However, the two were frequently spotted together in the years following, and in 2022, the couple revealed they reunited during the pandemic. They share two children, Ella and Quinlin.
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Allen Covert as Sammy
Since playing Robbie's eccentric best friend, Sammy, Allen Covert has regularly and closely collaborated with Sandler (his classmate at New York University), and was featured in movies like 50 First Dates (2004), Jack and Jill (2011) and Murder Mystery (2019).
Although he has distanced himself from acting, Covert can be seen in the credits as an executive producer and co-writer in most of Happy Madison Productions' films. He is also a co-writer on Sandler's musical comedy albums like What's Your Name? and Shhh... Don't Tell.
Covert married Kathryn Hagstrom in 2006, and the couple divorced in 2019. Together, they have four children.
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Angela Featherstone as Linda
After playing Linda, Robbie's fiancée who leaves him at the altar (and maybe even has a hand in breaking up Van Halen), Angela Featherstone appeared on television shows like Providence, The Guardian and Exes & Ohs. In 2016, she acted in My Dead Boyfriend, and in 2018, she held a small role in the Oscar-winning film CODA.
Featherstone has also written and directed a number of short films, including 2022's L'Étranger. She is an advocate for children in foster care, and in 2021, founded a nonprofit organization for children aging out of the foster care system — Fosteringcare.org.
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Matthew Glave as Glenn Guglia
After playing The Wedding Singer's antagonist, Julia's less-than-faithful fiancée Glenn Guglia, Matthew Glave appeared on television shows such as Revenge, The Closer, Hawaii Five-0 and The Rookie. He also appeared in Argo (2012), First Man (2018) and Funny Story (2018).
Glave is married to actress Anita Barone, with whom he shares two daughters, Madeline and Roxanne.
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Steve Buscemi as David Veltri
Although uncredited in the film for his bit part as the serenading David Veltri, Steve Buscemi has always been and will always be one of Hollywood's most recognizable set of eyes.
Buscemi has been busy in front of the camera since the '80s. In 1998, he acted in The Big Lebowski and Armageddon and went on to make dozens of appearances in film and on TV in the following years.
The actor scored the role of Tony Blundetto on The Sopranos — and directed a few episodes — and his lead role on HBO's Boardwalk Empire earned him a Golden Globe and two Screen Actor Guild Awards. Buscemi has also directed several films and episodes of 30 Rock, Nurse Jackie and Portlandia. He joined Pete Davidson on-screen in 2020's King of Staten Island, playing an FDNY firefighter — a job he held in real life in the early-1980s and again for the days following 9/11.
Buscemi was married to Jo Andres from 1987 until her death in January 2019. Together, they had one son, Lucian.
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Alexis Arquette as George Stitzer
Alexis Arquette played George Stitzer, a singer in Robbie's band and unabashed fanatic of Boy George — performing an epic rendition of "Do You Really Want to Hurt Me." In the years following the film's release, the actress and trans activist appeared on-screen in projects like She's All That (1999) and Friends, in which she shared scenes with her sister-in-law at the time, Courteney Cox.
Arquette also nabbed supporting roles in Pulp Fiction (1994), Threesome (1994) and Bride of Chucky (1998). She was sister to famed actors Rosanna, Richmond, Patricia and David Arquette.
In 2016, Arquette died due to complications from HIV; she contracted the virus in 1987.
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Ellen Albertini Dow as Rosie
Ellen Albertini Dow's role as rapping grandmother Rosie is one to remember. Afterward, the character actress landed countless guest roles on TV series like , Shameless, The Golden Girls, Six Feet Under and Scrubs. She also appeared in films like Wedding Crashers (2005) and She Wants Me (2012). Additionally, Dow was an acting coach who taught at colleges in Los Angeles.
Dow was married to her husband Eugene Dow Jr. until his death in 2004. In 2015, she died at the age of 101 from pneumonia.