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 was a model

Jackie Sandler was born in Coral Springs, Florida, in 1974 and grew up with three siblings (a sister and two brothers). She was raised by her mother Lila Titone and her father Joseph Titone. Her dad, a former state legislator, made headlines a few years before his daughter became newsworthy. In 1992, the South Florida Sun Sentinel reported that Joseph's law license had been suspended for five years after he was found guilty of unlawful compensation and perjury. 

That same year, Jackie graduated from Marjory Stoneman Douglas High School in Parkland, Florida. Her future husband, meanwhile, had already completed his college education, graduating from New York University's prestigious Tisch School of the Arts in 1988 with a Bachelor of Fine Arts in Drama and making his first appearance on "Saturday Night Live" in 1990.

We don't know whether Jackie was an "SNL" fan who saw her future husband on television while she was still in high school, but we do know that she was on the cheerleading squad (and we'd love to hear her thoughts about "The Cheerleader"). By the time she graduated, Jackie had already done some modeling. In 2000, the South Florida Sun Sentinel reported that she wasn't doing too shabby, raking in around $5,000 for each of her photoshoots. But like so many other successful models before her, Jackie decided to branch out and give acting a shot.

Two movies and one look was all it took

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.

She and Adam Sandler reportedly split over a prenup

In 2000, the South Florida Sun Sentinel reported that Adam Sandler and Jackie Sandler had started to discuss the possibility of getting hitched, but there was a hitch: apparently, Jackie didn't want to sign a prenuptial agreement. However, Adam's publicist denied that the couple was fighting over what would happen to their finances and property should they get divorced in the future. Jackie's father also made the case that his daughter had no reason to marry Adam solely for the millions of dollars in his bank account. "Jackie has a career of her own now," Joseph Titone pointed out, "and even if they're not married, I'm hoping they can still have a professional relationship."

Though the rumor mill talked of strife between the couple over finances, it's clear that Adam and Jackie are a team. And after being married to Adam for as long as she has, Jackie can now triumphantly point to their stacks of anniversary cards as evidence that she was in it for the Sandman and not his money.

The same year that the couple was hit with rumors that they had split, Jackie appeared in Adam's movie "Little Nicky." She played Jenna, one of the angels who helps her celestial sister Holly (Reese Witherspoon) greet Adam's titular character when he visits heaven.

Jackie Sandler converted to Judaism

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 serenaded her at their wedding

Adam Sandler has the wedding photos to prove that he did not get married in his signature baggy basketball shorts, oversized T-shirt, and tube socks combo. Instead, he wore a tux and yarmulke for the traditional Jewish ceremony at Dick Clark's Malibu estate. Adam even dressed his pet bulldog Meatball up in a miniature suit and matching yarmulke for the occasion, and the dapper doggo performed the role of ring bearer.

Jackie Sandler looked stunning in an ivory gown with spaghetti straps, a sweetheart neckline, and an A-line skirt. On "The Dan Patrick Show," Adam revealed that he serenaded his bride during the wedding with a new version of his beloved love song from "The Wedding Singer," "Grow Old with You" — "I wrote all the words for Jackie," he shared. The Daily News shared one of the tweaked lyrics: "You're the prettiest girl I know without an ounce of fat."

This wasn't the only musical surprise that Jackie got when she became Mrs. Sandler. Adam told Patrick that late rocker Tom Petty had a car crash near Clark's property and crashed the wedding to use their phone. Other famous attendees included Rodney Dangerfield, Jack Nicholson, and Jennifer Aniston. While there are a lot of brides who wouldn't want to share the spotlight with A-listers that their non-famous guests can't help but be starstruck by, Jackie clearly isn't one of them.

Jackie Sandler had to change a lot of diapers

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."

How Adam learned about Jackie's second pregnancy

When Jackie Sandler learned that she was expecting again in 2008, she enlisted her daughter's help to break the news to Adam Sandler that he was about to become an even bigger daddy. On "Live with Regis and Kelly" (as shared by People), Adam recounted how he arrived home one night to find that Sadie Sandler had been allowed to stay up late so that she could surprise him with a very special gift. "I open it up and it was one of those pregnancy [tests] and I was like 'Woowww,'" he recalled.

During Jackie's pregnancy, Adam was busy making the rounds to promote "You Don't Mess With the Zohan." It marked the first time Sadie appeared in one of her dad's movies, and her mom joined her. Their respective uncredited roles were "Girl riding on goat" and "Mom in line for Goat Ride." 

One of Adam's late-night stops was on "The Tonight Show," where he revealed that Jackie was experiencing some pretty gnarly morning sickness. It was so bad, in fact, that it was making Sadie worried. "I try to relax my daughter, just saying, 'Mommy's not like bad sick,'" Adam said. "'She just has something growing in her that's eventually gonna shoot out her vagina and take half your toys.'" When daughter No. 2 arrived, Adam and Jackie named her Sunny Madeline Sandler, giving her the same initials as her sister.

She doesn't get jealous of her husband's romantic leads

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.

Why Jackie Sandler got excited about stairs

In 2017, the comedy Adam Sandler sent down the Netflix assembly line was "Sandy Wexler," in which he plays a talent manager. Adam cast Jackie Sandler as one of his character's clients. That same year, Adam had another movie to promote, and while Jackie didn't make a cameo in it, she had a good reason to be really excited about it.

The film was "The Meyerowitz Stories," and it wasn't one of Adam's frivolous flicks that offers the same type of comforting escapism as a Hallmark movie. It had acclaimed director Noah Baumbach at its helm, and its marquee names included Dustin Hoffman, Emma Thompson, and Sigourney Weaver. Adam's rare straying into the more serious side of Hollywood earned him a ticket to the Cannes Film Festival, and Jackie couldn't wait to ascend the iconic red stairs at the Palais des Festivals with him. However, she was concerned that she might trip and fall. "So, we had a month before we went, and every staircase, we would practice," Adam revealed on "Conan."

But when the big moment came, a grouchy French official tried to keep Jackie at the bottom of the stairs while the movie's cast ascended them together. Adam begged the official to let him return to Jackie so she could walk up with him, but to no avail. "Then I hear — Dustin goes, 'Go get your wife,'" Adam recalled. After the Hoffman spoke up on behalf of the Sandman, the official relented, and Jackie got her moment on the stairs.

She convinced her husband to star in Uncut Gems

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.

Jackie Sandler works with her brother often

Like his sister Jackie Sandler, Chris Titone is an actor who often works with Adam Sandler. Titone also penned the screenplay for the 2022 movie "Home Team," which is about New Orleans Saints coach Sean Payton. Titone is married to Sean's daughter, sports broadcaster Meghan Payton, and it was her report about Sean coaching his son's youth football team that served as the inspiration for Titone's screenplay. Adam helped his brother-in-law bring his vision to life by producing the movie through Happy Madison.

Kevin James plays Sean in the movie, and Chris and Jackie both have small roles. Chris has also appeared alongside his sister in a number of other comedies, including "Bucky Larson: Born to Be a Star," "That's My Boy," "Grown Ups 2," "Blended," "The Wrong Missy," and "Hubie Halloween."

In the 2020 movie "The Wrong Missy," Jackie has a larger role than usual as the movie's villain, Jess, aka "The Barracuda" — she even gets to perform a choreographed dance routine. In the Netflix comedy, she and David Spade play co-workers competing for a big promotion. Jackie was apparently so excited about her own promotion that she joined Twitter to promote the movie, and she and Adam had nothing but love for her on-screen nemesis. "My husband told me to tell you that you look extremely cute," she tweeted at Spade during a watch party. She also shared a few behind-the-scenes photos, including one of Titone with his nieces. 

She and Jennifer Aniston want Adam Sandler to be healthier

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.

Her daughter Sunny Sandler landed a lead role

When Adam Sandler makes his productions a family affair (which is pretty much always nowadays), the casting can sometimes feel a bit awkward. This was the case with his 2023 Netflix movie, "You Are So Not Invited to My Bat Mitzvah." He gave his youngest daughter, Sunny Sandler, the lead role of Stacy, a girl who is looking forward to celebrating her bat mitzvah with her best friend — until said friend stabs her in the back by dating the guy she's been crushing on. 

Adam plays Stacy's father in the movie, and Sadie Sandler plays her sister. Variety found the latter casting to be a brilliant move, as it made the siblings' scenes together feel authentic. But for the role of his character's wife, Adam broke up his family unit with the casting of his "Uncut Gems" co-star Idina Menzel. Jackie Sandler didn't get left out, however; she plays the mother of Stacy's betraying bestie.

While the Sandler family was filming the movie together in Canada, Adam spoke to AARP about how his parenting style differs from that of his wife. He revealed that he's always trying to introduce his daughters to things he's passionate about, such as his favorite music. "My wife — and the shrinks — say I should just let stuff happen instead of getting so involved," he said. The couple are both focused on their family, and the actor also shared, "My wife and I go to sleep talking about the girls. They have so much ahead."

The Sandlers want to grow old with each other

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."