Adam Sandler is not everyone’s cup of tea. His movies tend toward the juvenile and so lots of people give him a wide berth at the box office. But to know Adam Sandler is to love him; in actors’ circles, he’s known as the nicest guy in Hollywood.

A little shy, Sandler does as little press as he can get away with, almost no print, and only very occasional talk show appearances, which he usually does in character. As the head of his production company, Happy Madison, things are a little different. He’s the affable and humble centre of an awful lot of industry, loyally employing friends and family on projects skewered by critics but beloved by audiences. Sandler’s movies haven’t been box office juggernauts in years, but they are consistent earners, and his name has continually if quietly stayed among the top earners of Hollywood for the past two decades.

Sandler’s early success meant he could start doing things his way, and he’s surrounded himself with the same cast of characters, working with the directors and writers he trusts, to say nothing of the famous faces appearing in his movies. Always grateful to Saturday Night Live as his diving board to fame (he was discovered by Dennis Miller), he employs not just the SNL alums he worked with (David Spade, Rob Schneider, Chris Rock, Norm MacDonald) but many besides (Will Forte, Andy Samberg, Dan Aykroyd, Kevin Nealon, Rachel Dratch). He attracts big names to his movies (Jack Nicholson, Harvey Keitel), but always finds room for old friends (Allen Covert, Peter Dante), Sandler mainstays (Henry Winkler, Kevin James, Steve Buscemi), and his own wife and daughters.

One such person who can never get enough is Drew Barrymore. In her 2015 memoir Wildflower, Barrymore describes begging for a chance to meet him after her good friend Tamra Davis (director of Billy Madison) raved about him. Barrymore was certain of his “goodness” and felt they should pair up despite them being complete opposites in their early 20s, “like a preppy and a punk set up on a bad blind date.” Her pitch worked: pretty soon he came calling with a little movie called The Wedding Singer in his pocket. Written by Sandler groupie Tim Herlihy, it was given an uncredited polish by Sandler’s friend and former roommate, Judd Apatow (another guy famous for working with a loyal crew, including Sandler himself of course, most notably on Funny People) and Carrie Fisher, to give equal weight to the feminine side. The movie was a hit, with Drew certifiably falling in love with the Sandler crew, calling them “real, no-bullshit friends” which I take is a high compliment in Hollywood.

People loved The Wedding Singer for many reasons – the 80s nostalgia, the cheesy music, but above all, the incredible chemistry between Adam and Drew (she refers to him as her “cinematic soulmate”).

Always intending to work with Sandler again, Barrymore knew they couldn’t settle for anything less than the greatness they’d already achieved. But life moved on. Drew worked intensely on a Penny Marshall movie called Riding in Cars with Boys, and it was around that time that she came across a romantic script that she thought was a great fit for her production company, Flower Films. Unfortunately that script was a hot commodity, and it kept changing hands, with big directors and stars attached, never becoming available to her, despite numerous attempts. Until one day she heard that it had landed at Adam’s studio, Happy Madison. By this time they each had an office just a few hundred feet apart on the Sony lot (she was doing Charlie’s Angels), so he was easy to hound. Sandler was already turning it into a comedy but welcomed Drew on board not only as a co-star but also as co-producer, and she’s responsible for keeping the important elements of the love story, the parts that turned us all to mush.

Adam and Drew took the Seattle drama and laid it out in Hawaii instead, each bringing their production families to paradise and basically turning the island into a happy party (so happy that her Angels co-star Cameron Diaz came to visit and never left). 50 First Dates opened on Valentine’s day, and I was there, butt in the seat, and actually watched it twice (the projector broke down half way through, and we had to star the thing over from the beginning). They broke records that opening weekend; I’m not the only one who finds these two irresistible.

It would be another decade before they reunited on-screen again, with The Wedding Singer director Frank Coraci back at the helm for a movie about modern families called Blended. This movie would be proof of how far they each had come, personally and professionally, since first meeting as successful, hard-partying kids in the 90s. Sandler, once a “bad boy of SNL” now has a reputation for being a family man. He has always been quick to attribute credit to his parents (his highest-grossing comedy album named for them, Stan & Judy’s kid, and even one of Chris Rock’s albums a tribute to Sandler’s late father). By this time Adam and Drew had 3 daughters between them and the whole crew headed to Africa, families in tow. Barrymore has downshifted on her acting career since becoming a mother, finding it hard to strike the balance, but an Adam Sandler film “celebrates wives and kids” and she was able to make a family adventure out of it, even discovering on her last day of shooting that she was pregnant with a second daughter.

Still the best of friends, Adam and Drew now attend each other’s kids’ birthday parties (2 daughters apiece – Sadie and Sunnie for him, Olive and Frankie for her) and talk about their next project, whatever that may be, joking that they’ll still be making romantic comedies when they’re old and gray. (In fact, during press for the movie Blended, Adam made a very pregnant Drew cry when he sang the precious The Wedding Singer song to her “I Want to Grow Old With You”).

No matter what it is, I know I’ll be in line to see it. These two are cute as can be when they’re together, and Drew knows why: “I once knew a boy named Adam. And I hoped that we could be a team, but what I found was a true partner. I now know a man named Adam, and trust me when I say, he is as great as you want him to be.”