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Drew Barrymore, 49, shares rare throwback snap with Adam Sandler from over 20 years ago

by LJ News Opinions
May 11, 2025
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Drew Barrymore took a walk down memory lane and shared and old photo of herself and good friend Adam Sandler on the set of 50 First Dates.

The actress and talk show host posted the throwback snap on her Instagram page, showing them together in-between takes from the 2004 film.

‘Throwing it back @adamsandler,’ the former E.T. the Extra-Terrestrial star, 49, wrote in the caption.

The image was taken at the site of their scene where Sandler’s character Henry Roth, a marine veterinarian with a habit of wooing women and a fear of commitment, was serenading Lucy Whitmore, played by Barrymore.

In the picture, seemingly taken during a brief break in the shoot, the two stars leaned their heads close to each other while sitting together.

The veteran actor and comedian still has his guitar in hand, while dressed in the Hawaiian-style garb, as The Drew Barrymore Show host was wrapped in a blanket over the rest of her summer-style costume.

Drew Barrymore shared a throwback snap on Instagram of the actress with Adam Sandler that shows the old pals and co-stars on the set of their hit rom-com 50 First Dates (2004)

Barrymore's Instagram photo was taken at the site of their scene where Sandler's character Henry Roth serenades Lucy Whitmore, played by Barrymore

Barrymore’s Instagram photo was taken at the site of their scene where Sandler’s character Henry Roth serenades Lucy Whitmore, played by Barrymore

The romantic comedy film, directed by Peter Segal, turned out to become a hit with fans, grossing $198.5 million at the worldwide box office, while working with a $75 million budget.

Just last week, Barrymore named Sandler, 58, as her best on-screen kiss, all while making the distinction that they’ve always been just friends.

‘I mean, I love that Adam Sandler and I are so platonic,’ Barrymore revealed during an appearance Watch What Happens Live With Andy Cohen. ‘We never dated, his wife Jackie is my dear friend.’

She added, ‘But I love being in films with him, because I think we’re representing something bigger than hot, sexual chemistry. We’re representing true admiration of another person.’ 

The Barrymore-Sandler pairing in film began with The Wedding Singer (1998), another rom-com that was hailed by critics and fans alike, that is widely considered one of Sandler’s best comedies.

Produced with just a budget of $18 million, the movie was a breakout smash for all those involved, globally grossing $123.3 million.

The two pals most recently starred in the film Blended (2014), which also ended up being a financial success with $123 million in box office receipts, although it wasn’t as well received by critics.

Last year, Barrymore confessed she’d like to do a fourth film with the former Saturday Night Live alum, along with his other frequent on-screen star, Jennifer Aniston, in the likes of Three’s Company or Death Becomes Her. 

The Drew Barrymore Show star has worked with Sandler in three romantic comedy films; the ET star is seen in January

The Drew Barrymore Show star has worked with Sandler in three romantic comedy films; the ET star is seen in January

50 First Dates was a hit with fans, grossing $198.5 million at the worldwide box office

50 First Dates was a hit with fans, grossing $198.5 million at the worldwide box office

Just last week, Barrymore named Sandler as her best on-screen kiss during an appearance on Watch What Happens Live With Andy Cohen

Just last week, Barrymore named Sandler as her best on-screen kiss during an appearance on Watch What Happens Live With Andy Cohen 

The Barrymore-Sandler film pairing began with the smash hit, The Wedding Singer (1998)

The Barrymore-Sandler film pairing began with the smash hit, The Wedding Singer (1998)

The former child star, who also starred with the SNL alum in Blended (2014), has let it be known she'd like to do a fourth film with Sandler, along with Jennifer Anniston; the old pals in 2014

The former child star, who also starred with the SNL alum in Blended (2014), has let it be known she’d like to do a fourth film with Sandler, along with Jennifer Anniston; the old pals in 2014

‘We’re so close. We text all the time. We see each other. We text,’ Barrymore told ET at the time.

‘I’m so busy talking to him and Jennifer Aniston about doing a threefer, if you will. I really want to make it happen. Timing is everything.’

She added, ‘We’re all producers. So we all have companies. So we can make this happen, and I think it’s a matter of timing.’ 

In 2022, Barrymore welcomed Sandler to her daytime show and proceeded to introduce him as ‘the best cinematic soulmate and partner,’ according to the NY Post.

During the segment, the duo went on to chat about their shared on-screen history together and possibly joining forces again to make another film. 



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Tags: adam sandlerandy cohendailymailDrew BarrymoreJennifer Anistonusshowbiz
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