The Stunning Transformation Of Jackie Sandler

Before comedy fans' favorite Sandmanchild became one of the "Grown Ups" and got married to Jacqueline "Jackie" Sandler (née Titone), he'd made at least one prior attempt at making it to the altar. But Adam Sandler's engagement to cosmetics company manager Margaret Ruden ended well before he played a wedding singer in his classic 1998 rom-com.

After his relationship with Ruden fizzled out, Adam was next romantically linked to "Clueless" star Alicia Silverstone, who supported her rumored boyfriend by rocking a "Happy Gilmore" T-shirt and hat at the movie's 1996 premiere. 

Unlike Silverstone, Jackie was an unknown actor when she captured Adam's heart, and "Happy Gilmore" is now one of only a handful of the comedian's movies that his wife doesn't appear in. Before Adam met Jackie, his leading ladies on screen included Bridgette Wilson in "Billy Madison," Julie Bowen in "Happy Gilmore," Drew Barrymore in "The Wedding Singer," and Fairuza Bulk in "The Water Boy." For a while, he believed his success put him at risk of missing out on a real-life happy ending and having to settle for living vicariously through the lucky-in-love heroes of his fluffy popcorn comedies. "The problem with me, as far as getting married and having a family, is that my comedy is so important to me," he once said, per the Daily Mail. But in Jackie, Adam found someone who would support him every step of the way as he pursued his dream — and who shared his desire to make his comedy career a family affair.

Jackie Sandler made her big-screen debut in the 1999 Rob Schneider movie "Deuce Bigalow: Male Gigolo," which was the first movie produced by Adam Sandler's Happy Madison production company (in one scene, an unseen and uncredited Adam can actually be heard shouting "Freak!" at Deuce and one of his clients).

In the film, Jackie plays a close pal of Deuce's love interest, Kate, who has no idea that her well-meaning but misguided friends hired the titular male prostitute to show her a good time. Jackie made enough of an impression on Schneider that he convinced Adam to cast her as a waitress in his 1999 comedy "Big Daddy." In a brief scene, she chats to Julian (who was played by the Sprouse twins) after being surprised to see the little boy sitting alone at a table in the sports bar where she works.

In some of his sweet Instagram tributes to his wife, Adam has revealed that he immediately knew Jackie was the one. "My heart has been yours since the first second I saw you and I love and appreciate your devoted soul more and more each day," he wrote when the couple celebrated 20 years of marriage in 2023. From the sound of it, Jackie felt the same way. "22 years ago today we locked eyes and fell deep. Look forward to the next 22, young lady," he captioned a July 2020 post.

After Adam Sandler popped the question in 2002, Jackie Sandler demonstrated just how devoted she was to her hubby-to-be by converting to Judaism. Shock jock Howard Stern brought this up when Adam appeared on "The Howard Stern Show" in 2015, and Adam shared why it's important to him that he and his family continue to honor his Jewish heritage. "I'm not crazy religious ... but I'm proud of being a Jew, and that's what I am," he said. Jackie helped him celebrate that pride by voicing a character in his 2002 animated movie "Eight Crazy Nights," which takes place during the Hanukkah season.

While Jackie loved her future husband so much that she was willing to change her entire religion for him, Adam told former "Good Morning America" host Diane Sawyer that he was super nervous about popping the question. "I played basketball that afternoon, trying to calm down, and then I was driving, I was saying the stuff out loud and trying to, you know, make sure I hit all of the right things so she would remember nice stuff," he recalled. 

He later learned that his proposal had earned the approval of Jackie's mother and grandmother when she phoned them to share the happy news; according to Adam, they celebrated loudly. As for his own verdict of his performance when it was game time after that basketball game, he said, "I did all right."

Adam Sandler and Jackie Sandler welcomed their first child, Sadie Madison, in 2006. And no, her middle name inspo was not the titular teacher-groping goof-off depicted in "Billy Madison." Adam explained to Blackfilm, "My wife wanted Madison for her grandfather and to have some New York in the kid." While Adam might not be a hardcore adherent of the slacker lifestyle like Billy is, he has confessed to being pretty hands-off when it came to the messier aspects of caring for a baby. When asked if he ever gave Jackie a break from being on diaper duty, he said, "I see that go on. I'm cheering on my wife. I'd say, 'Way to go. Can I have some milk?'"

From the sound of it, Jackie didn't get a lot of help with much of anything when she and Adam were adjusting to life as first-time parents. "If she asks me to go get that ointment, I run out and get it, but that's about it, man," Adam told Access. He's also not a fan of chores in general. On "The Dan Patrick Show," he revealed that Jackie quit asking him to help out with the housework early in their marriage. He might not have been a team player at home, but the couple sure do work well together; the year after she became a mom, Jackie played a teacher in Adam's movie "I Now Pronounce You Chuck and Larry."

When Adam Sandler starred alongside Katie Holmes in the 2011 comedy "Jack and Jill," it was one of the rare instances where Jackie Sandler didn't have a cameo in the movie. On "The Late Show," Sandler recounted the awkward moment when Holmes' then-husband, Tom Cruise, told him that he found it "bizarre" that his wife was playing Sandler's wife in the movie. Sandler then explained why Jackie Sandler wasn't jealous over the situation. 

He recalled telling Cruise, "Anything I do with your wife in the movie, you can do with my wife." When Jackie heard this, she wanted her husband to make some last-minute screenplay changes. "Every morning I'd go to the set and hear my wife go, 'Please do a love scene,'" Adam continued.

According to Adam, Jackie often gives him feedback on his romantic scenes, and when it's negative, it's not because she feels like he's too into his leading ladies. Jackie had a role as "Hollywood Stepmom" in the movie "Blended," so she was on set when Adam had to film kissing scenes with his co-star Drew Barrymore. "My wife loves Drew so much that she encourages me. There's no jealousy at all; she's just like, 'Get in there!'" Adam shared on "The Ellen DeGeneres Show." Barrymore was also on the show at the time and revealed that she's seen Jackie give Adam a stern talking to when one of his lip locks lacks passion.

While Adam Sandler successfully ventured beyond the artistic confines of his usual juvenile comedic jaunts for "The Meyerowitz Stories" and "Punch-Drunk Love," he was still reticent to sign on for the Safdie brothers' anxiety-inducing 2019 drama, "Uncut Gems." "I read the script, and I was terrified," Adam said on "The Dan Patrick Show." Jackie Sandler also read it, and she knew that her husband couldn't turn the role down. "She just calmed me down and said, 'You can do all this stuff and commit to it and jump in,'" Adam recalled.

On "The Ellen DeGeneres Show," Adam revealed that Jackie often helps him decide what projects to take on. "She gives me strength and courage to jump into this stuff," he said. In "Uncut Gems," he plays a jeweler named Howard, and he shared that he was gifted a diamond necklace embellished with the character's name. Adam told W Magazine that Jackie started wearing it to red-carpet events ahead of the movie's release. "She looks cute in it. I like it," he said.

Jackie's help with shaping Adam's filmography doesn't stop there; Adam's Netflix movie "Murder Mystery" came out the same year "Uncut Gems" did, and it co-starred Jennifer Aniston. On "Conan," Adam shared that Jackie was critical of his kissing scenes with the "Friends" star, explaining, "She wants me to go harder." He also revealed that Jackie was rubbing off on Sadie and Sunny. "My two daughters are like, 'Come on, be nice to Jennifer. Kiss her good,'" he continued.

After appearing alongside Jennifer Aniston in "Just Go with It" and "Murder Mystery," Jackie Sandler became one of "The Morning Show" star's biggest fans. "My wife loves Aniston, thinks she's great," Adam said on "The Howard Stern Show." "She just loves everything Jennifer has to say about anything." This includes Aniston's recommendations for what Adam can do to improve his health, and in 2021, Adam told The Hollywood Reporter that the two women had ganged up on him for his own good. "They want me to stretch more — eventually be able to touch my toes, which I'm about nine inches away from," he shared.

During a 2023 appearance on "The Tonight Show," Aniston revealed she also gives her good pal Adam herbal remedies and green smoothies, but she just can't seem to get the comedian on a health kick that sticks. "Jackie's like, 'Thanks, it lasted about a minute,'" she said.

According to Adam, his wife and Aniston really enjoy talking to each other, and he told Extra that one of their favorite topics of conversation is Jackie's complaints about his behavior. He once gave the two women plenty of time to gossip about him during a party at Aniston's house. On "Live with Kelly and Ryan," Adam recounted how Jackie and Jennifer were having so much fun that he stretched out on the floor inside her closet because he couldn't get Jackie to leave when he was ready to.

In a 2023 interview with ET, Jackie Sandler shared one of the secrets to her lasting marriage with Adam Sandler, the length of which is a bit of an anomaly in Hollywood. "He's always trying to make me laugh and I'm always trying to make him laugh, so it works out," she said. 

Jackie rarely makes public comments about her husband, but it became apparent that she shares his sense of humor when she helped honor him during his Mark Twain Prize for American Humor award ceremony at the Kennedy Center in 2023. "Yes, he's just as funny in real life as he is in the movies," she told the crowd, per The Washington Post. "And he's just as good in bed as you've all imagined for so long. Adam, whether you're awake or not, it's always fantastic."

After almost a quarter of a century with Jackie, Adam still compliments her, telling ET that he's especially fond of her legs. But the Sandlers haven't just been together so long because they still find each other attractive and can still laugh together; their connection is much deeper than that. Sandler told AARP that being encouraging and attentive spouses has helped keep their bond strong, but it's really just about wanting to grow old with each other. "We try our best — that's all," he said. "And we don't ever think of not being together. We always talk about our future together."