After starring in several expensive flops, they each topped Forbes magazine's list of the most overpaid actors in Hollywood in recent years.
Yet Adam Sandler and Drew Barrymore continue to bask in the afterglow of their biggest hits together, 1998's The Wedding Singer and 2004's 50 First Dates - films that made such good use of their sweet, goofy chemistry that they still feature on Best Romantic Comedies Of All Time type lists today.
This, along with their individual star power, is presumably why they got away with making their latest turkey, Blended - a film that spectacularly misjudged its audience when it debuted in the United States last month.
Opening in Singapore today, the romantic comedy - about two single parents trying to find love and blend their respective families together - has barely managed US$30 million (S$38 million) at the US box office - considerably less than expected and nowhere close to the US$80 million and US$120 million racked up by The Wedding Singer and 50 First Dates. However, Blended is still on track for a global release in over 55 countries.
Speaking to reporters in Los Angeles shortly before the US premiere, the pair admit, as many industry veterans do, that they are still none the wiser about what will end up connecting with audiences.
"I have no clue what's going to work and what's not going to work," says Sandler, 47, at a press conference with the cast of Blended.
He adds with a dry laugh: "I've had some not work."
"We just try to make the best movie we can," he says, nodding at frequent collaborator Frank Coraci, who directed this film as well as The Wedding Singer and Sandler's other hits, The Waterboy (1998) and Click (2006). "We try and make something that we think we'd want to go see."
As he and Barrymore sit side by side - beaming at each other and finishing each other's sentences - it is obvious that there is real affection between the two, who have been fast friends for more than a decade.
This is another reason they decided to team up again after all these years.
"I love Adam so much," gushes Barrymore, 39, revealing it was she who first pursued him and convinced him to work with her on those early films.
She says: "I was just so smitten with him and such a super, giddy fan. Like this person is just so wonderful and I believe in him so much that I stalked him, called him, asked him to have lunch with me and convinced him that I absolutely knew we were supposed to partner up.
"And I'm still convinced to this day that it's the best thing I've ever done in my life, as far as my job and my life is concerned. He is the best partner I've ever had, honestly. It's a partnership, it transcends even romance."
Sandler is more succinct but no less complimentary.
"She's a nice girl," he says. "I've known her a long time, she knows a lot about me and we have no secrets and we're pretty close."
Overall, the actors each have had more than their share of successes, individually as well as together.
A child star since her breakout role as the adorable Gertie in Steven Spielberg's smash hit E.T. (1982), Barrymore became a cautionary tale for the pitfalls of becoming a celebrity at a young age, with stints in rehabilitation for drug and alcohol issues as well as a suicide attempt - all before she was 15 - well catalogued in the press.
Her personal life also became a bit of a punchline after a string of failed relationships and two shortlived marriages (to Los Angeles bar owner Jeremy Thomas in 1994 and actor Tom Green in 2001) that lasted a combined seven months.
But the actress remained much beloved through it all, thanks to her sunny persona both on and off screen.
Professionally, she eventually turned things around in the late 1990s, co-founding a production company, Flower Films, that churned out a steady stream of comedic hits for her to star in, notably Charlie's Angels (2000) and He's Just Not That Into You (2009).
Two years ago, she settled down with husband number three, art consultant Will Kopelman, with whom she has two daughters - Olive, one, and Frankie, who was born in April.
Sandler, who has two daughters - Sadie, seven, and Sunny, five - with Jackie, his wife of 11 years, had a far less turbulent path to the top.
He went from stand-up comic to a role on the television sketch show Saturday Night Live, to a prolific career as a movie funnyman.
His stock-in-trade - juvenile humour and silly songs - does not typically impress the critics, but audiences have lapped it up nonetheless with movies such as Happy Gilmore (1996), Big Daddy (1999) and, more recently, Grown Ups and Grown Ups 2 (2010 and 2013) and the animated feature Hotel Transylvania (2012).
But there have also been bombs such as Jack & Jill (2011) and That's My Boy (2012), leading industry observers to predict that he may not be able to command the US$15 million pay cheques he once did for much longer.
Nonetheless, he and Barrymore - who at one point was reportedly earning up to US$12 million a film - are still big enough stars that reuniting them for Blended probably sounded like a great idea on paper.
The actors themselves wanted to come back and make a romantic comedy that was more reflective of the fact that they have both grown older and become parents.
"When we did The Wedding Singer way back, it was a very honest, young point of view on love," explains Coraci.
"And (Blended) was sort of a more grown-up take on how, as life goes on, you deal with certain situations that are trickier. And this movie sort of captures that as a funny journey."
"It was exciting to get such an amazing cast together to do it. And to bring Adam and Drew back, it was a great feeling."
The actors could not wait to be on a set together again - and this time around, they were also bonding over the fact that they each have two daughters.
Sandler was drawn to the story because it said something about parenthood as well as romance.
"It's about being good parents and wanting to raise a family and create a nice environment for the kids to grow up and feel safe in.
"I knew we wanted to make a funny movie and I knew we wanted to make a romantic movie, but I love the message of just saying that if you commit to being a good parent, you've got to be a good parent," he says.
That belief is very much a part of who the actor is, says his co-star.
"Adam's always been an amazing, dedicated father in real life and his relationship with his daughters in the movie is so delicious and warm," says Barrymore of her co-star, whose daughters in the film are played by Bella Thorne, 16, Emma Furhmann, 12, and Alyvia Alyn Lind, six.
She and Sandler tell Life! that being able to have both their families on the set was one of the great joys of working on this film.
She says: "There are certain types of sets or directors or actors who you don't feel as comfortable being a family person around - you just don't feel like they're invited."
He nods in agreement.
The Blended set, which was staffed by many of the production crew that Sandler often works with, was the opposite of that.
"It's like the kids are around and everybody's happier, says Barrymore. "Life is better."
Blended opens in cinemas here today