‘The Wedding Singer’ celebrates 25th anniversary: Drew Barrymore, Adam Sandler then and now

It's been 25 years since "The Wedding Singer" was released.

The movie told the story of Robbie Hart (Adam Sandler), one of the most popular wedding singers in the game who thought he had it all, only to get left at the altar on his own wedding day. Through a crazy turn of events, Robbie realizes he's in love with Julia Sullivan (Drew Barrymore), a waitress he met while performing at a wedding, and has to hustle to win her over before she marries the wrong guy.

Here is what the cast of "The Wedding Singer" has been up to since the release of the movie.

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Adam Sandler had already written and produced a few successful films prior to starring as Robbie Hart in "The Wedding Singer," including "Billy Madison" and "Happy Gilmore," not to mention having been a cast member of "Saturday Night Live" for five years from 1990 to 1995. 

He continued his run of successful comedies after the "Wedding Singer," starring in "Big Daddy," "The Waterboy," "Little Nicky," "The Animal" and "Anger Management" with Jack Nicholson. In 2004, he reunited with his "The Wedding Singer" co-star star, Drew Barrymore, in the movie "50 First Dates."

He followed "50 First Dates" with "The Longest Yard," "Click," "I Now Pronounce You Chuck and Larry" and "You Don't Mess With the Zohan." In 2010, he appeared alongside an all-star cast in "Grown Ups," which he also wrote, returning in 2013 for its sequel, "Grown Ups 2."

That same year, he starred in "Just Go With It" alongside Jennifer Aniston. In 2014, Sandler reunited with Barrymore again, starring alongside her in the romantic comedy "Blended."

In 2019, Sandler and Aniston teamed up for the comedy "Murder Mystery," in which their characters are accused of murder, and they try to find the actual culprit. Also in 2019, Sandler starred in "Uncut Gems." 

Most recently, Sandler starred in "Hustle," which earned him his first ever Screen Actors Guild nomination in 2023. A sequel to "Murder Mystery," titled "Murder Mystery 2," is set to premiere on Netflix on March 31, 2023.

Sandler started his own production company, Happy Madison, in 1999 in partnership with Rob Schneider, who appeared on "Saturday Night Live" with him. The company produced many films which he starred in, as well as others, including "The House Bunny," "The Benchwarmers" and "The Master of Disguise."

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The actor has been married to Jacqueline "Jackie" Sandler since 2003. The couple has two daughters, Sadie and Sunny. His wife and daughters often make appearances in his films.

Drew Barrymore, a member of the Barrymore acting dynasty, appeared on-screen for the first time at three years old. She won over fans at the age of seven in "E.T. the Extra-Terrestrial" and then again at 8-years-old in "Firestarter." 

A few years before "The Wedding Singer" was released, Barrymore started her own production company, "Flower Films," at the age of 20. The first movie she produced with the company was 1999's "Never Been Kissed," one of the actress' most recognizable roles. The following year, she produced and starred in "Charlie's Angels," alongside Cameron Diaz and Lucy Liu, with all three coming back for the 2003 sequel "Charlie's Angels: Full Throttle."

She then starred in "Donnie Darko," "Riding in Cars with Boys" and "Confessions of a Dangerous Mind," which was George Clooney's directorial debut. She also co-produced and starred in "50 First Dates," with Sandler.

In addition, Barrymore has produced and starred in a string of successful movies such as "Fever Pitch," "Music and Lyrics" with Hugh Grant, "He's Just Not That Into You" and "Whip It," which was also her directorial debut.

In 2014, she reunited with Sandler in the 2014 comedy "Blended," in which she played a single mom who falls for Sandler's character after being forced to go on vacation with him. She then starred in Netlfix's "The Santa Clarita Diet," as Sheila Hammond, a realtor who gets infected with a virus that turns her into a zombie. Although popular, the show was canceled after three seasons.

Since 2020, Barrymore has been hosting her own daytime talk show, "The Drew Barrymore Show," recently announcing the show was picked up for a fourth season.

Barrymore has been very vocal about her troubled past as a child, partying at Studio 54 as a young girl and going to rehab for alcohol and drug addiction when she was 13.

She emancipated herself from her parents at the age of 15 and moved into an apartment on her own, officially putting drugs and alcohol behind her.

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The actress was first married to Jeremy Thomas for less than two months in 1994. A few years later in 2001, she married comedian Tom Green, but the marriage didn't last long and the two were divorced in 2002. Barrymore went on to marry art consultant Will Kopelman in June 2012. The couple welcomed two daughters, Olive and Frankie, before getting divorced in August 2016.

Christine Taylor was already a successful actress, having played Marcia Brady in "The Brady Bunch Movie" and its sequel "A Very Brady Sequel," when she landed the role of Holly in "The Wedding Singer." 

After the success of "The Wedding Singer," Taylor maintained a successful career, appearing in feature films, including the 2001 comedy "Zoolander," also starring Ben Stiller, Owen Wilson and Will Ferrell, and the 2008 comedy "Tropic Thunder." She later made guest appearances on "Curb Your Enthusiasm," "Hannah Montana," "Arrested Development" and "My Name is Earl."

The actress continued to work steadily throughout the years, returning to the character of Matilda in "Zoolander 2" in 2016, the Netflix show "Insatiable" and "iCarly." Most recently, Taylor acted in "Search Party," "Severance" and "High Desert."

Taylor met and started dating Ben Stiller in 1999.

The two were married a year later in May 2000 and have since welcomed two children together, a daughter Ella and a son Quinlin Dempsey "Quinn." 

They announced they were separating in 2017, after 17 years of marriage, however after living together during the COVID-19 lockdown, the two reconciled.

Alexis Arquette had her first acting role at the age of 12, and had already starred in a number of successful movies, including "Of Mice and Men" and "Pulp Fiction," before appearing as George Stitzer, a Boy George enthusiast, in "The Wedding Singer."

Her success in the business didn't stop there, as she continued to appear in successful films, like "Bride of Chucky" and "She's All That," and made guest appearances on the shows "Felicity" and "Beggars and Choosers." She later starred in "Xena: Warrior Princess" and had a guest role on "Friends," sharing scenes with her then-sister-in-law Courtney Cox.

She chronicled her transition and the process of her sex reassignment surgery in the 2007 documentary "Alexis Arquette: She's My Brother."

Following her transition, she starred in "Hard Breakers," "Here & Now" and "Getting Back to Zero." Her final role was in the 2014 Adam Sandler and Drew Barrymore comedy "Blended," in which she played a Boy George impersonator, an homage to her character in "The Wedding Singer."

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Alexis, who had battled HIV for 29 years, died at the age of 47 in 2016 from a heart attack.

Matthew Glave already had multiple film roles under his belt before taking on the part of Glenn Guglia in "The Wedding Singer."

Glave also appeared in 11 episodes as Dr. Dale Edson in "ER" from 1996 to 2002. In that time, he also appeared in "NYPD Blue," "Charmed," "Touched By An Angel" and "The X-Files."

He went on to appear in "Will & Grace," "The West Wing," "Life on a Stick" and "The New Adventures of Old Christine" with Julia Louis Dreyfus.

He had a small part in "Get Smart," starring Steve Carell and Anne Hathaway, a 16-episode arc on "Army Wives" and "Girlfriend's Guide to Divorce," and he appeared in "Desperate Housewives" and "Revenge."

Most recently, he starred in "Angie Tribeca," "The Santa Clarita Diet," "Better Things" and "The Rookie," which is currently in its fifth season.

Glave has been married to actress Anita Barone since 2000, and the couple have two daughters together, Madeline and Roxanne.

Angela Featherstone took on the villain role in "The Wedding Singer," playing Linda, the woman who left Adam Sandler's Robbie at the altar because she couldn't stand being married to a wedding singer. Prior to the movie, she was known as a top model, and for playing the woman Ross cheated on Rachel with on "Friends."

After "The Wedding Singer," Featherstone went on to appear on "Seinfeld," had a starring role in "Cracker: Mind Over Murder," as well as appeared in episodes of "Jack & Jill" and "Providence," and the films "Soul Survivors" and "Reeseville."

The actress then had a 10 episode arc on "The Guardian" and a 14 episode arc on "Exes & Ohs." Most recently, she appeared in the HBO show "Girls," the Showtime series "Ray Donovan" and the film "My Dead Boyfriend."

In 2022, Featherstone made her directorial debut with the seven-minute short film "L'Étranger."

Starting with "Going Overboard," Allen Covert made multiple small appearances in Adam Sandler's movies, before getting a large role as Robbie's best friend Sammy in "The Wedding Singer."

After his first big role, Covert continued acting almost exclusively in films produced by Sandler's production company, including "The Waterboy," "Never Been Kissed," "Big Daddy," "Little Nicky" "Anger Management" and "50 First Dates."

In 2006, Covert landed his first, and only, leading role in a film in the movie "Grandma's Boy," which follows the story of a 35-year-old man who has to move in with his grandmother and two of her elderly friends. 

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As an executive producer at Happy Madison Productions, many of Covert's roles have been in films produced by the company, including "The Longest Yard," "I Now Pronounce You Chuck and Larry," "Just Go With It," "Grown Ups 2" and "Blended."

Most recently, he appeared in "Murder Mystery," "Hubie Halloween" and "Home Team." In addition to his acting credits, Covert has served as a performer, writer and producer for almost every film and comedy album Sandler has ever released.

Covert married Kathryn Ashley Hagstrom in February 2006. After 13 years together, the couple filed for divorce in July 2019, which was finalized in November of that year.

Ellen Albertini Dow was already an accomplished actress before she became known as rapping grandma Rosie in "The Wedding Singer." That same year, she appeared in an episode of "The Nanny," and starred in the movie "Patch Adams" with the late Robin Williams.

She went on to appear in "Will & Grace," "Yes Dear" and "Scrubs." From 2001 to 2002, Dow starred as Grandma Harriet Krupp on "Maybe It's Me," however the show only lasted one season.

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Dow then starred in "Wedding Crashers" with Owen Wilson and Vince Vaughn, "My Name is Earl," "Fat Girls," "Hannah Montana," "According to Jim" and "Shameless." Her final on-screen roles were in "New Girl" and "Frank the Bastard" in 2013.

Prior to acting, Dow taught drama at Los Angeles City College, and later at Los Angeles Pierce College. She and her husband started the Albertini Mime Players, and produced its productions for 19 years.

Dow married Eugene Dow Jr. in June 1951, and remained married to him for 53 years until his death in October 2004. The actress died in May 2015 at the age of 101 due to complications associated with pneumonia.