One of comedy's most recognizable icons, Adam Sandler's wildly successful acting career contains some of the highest highs, but also the lowest lows. For every Uncut Gems, there's a Jack and Jill. For every Grown Ups 2, there's Grown Ups. At his best, Sandler is one of the finest and funniest actors in all of Hollywood. At his worst, he's needlessly raunchy and distasteful. With such a vast filmography, it can be hard to pinpoint when Sandler is on his A-game. But a cursory glance at his best films and performances leads to one consistent factor: his impeccable chemistry and compatibility with Drew Barrymore. Barrymore and Sandler have co-starred in three films: The Wedding Singer, 50 First Dates, and Blended. Each of these films came out in different decades, yet they each feature Adam Sandler at his very best. The pinnacle of Sandler's performances are a product of his own comedic skills, but are elevated to new heights because of Barrymore's own wit, cheer, and heart. Considering the breadth of his acting career, it would be a disservice to say that Sandler only performs well alongside Barrymore. But if you're looking for the very best from Adam Sandler? If you want him at his funniest, most sincere, and most genuine? You need Barrymore to help push him to those incomparable heights.

So, what is Adam Sandler's peak? As an actor who predominantly plays comedic roles, opinions on Sandler largely relate to a person's sense of humor. This means that if you don't connect with his jokes, you wouldn't fully appreciate his performance. So to identify Sandler's best, you have to note when he's at his funniest. However, over the years he has proven that he is more than just a slapstick actor with funny voices and facial expressions. He's a bona fide Thespian who can be truly sincere and magnetic — just refer back to Uncut Gems. If he has such a range as an actor, his best work must also include the ability to be grounded and serious as well.

True to his own sense of style, Sandler is also Hollywood's funniest dad. You respect and appreciate all he's done and are equally likely to cringe or laugh at his jokes. Adam Sandler's ability to include a sense of comfort and familiarity in his performances is also a necessary feature to consider. The very best of Sandler involves a combination of these factors, something that appears in many of his films. However, the it-factor to pushing these traits to their absolute maximum is his deep friendship and camaraderie with Drew Barrymore.

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Adam Sandler and Drew Barrymore's Real Friendship Comes Across On-Screen

Drew Barrymore as Lucy and Adam Sandler as Henry in 50 First Dates
Image via Sony

One of Sandler's most defining and endearing qualities is his loyalty to his friends and fellow actors. Many of his films feature his friends in both leading roles and cameos; Grown Ups essentially feels like he just got his funniest friends to go on vacation with him. Though he's had countless actors play his friends on screen, Barrymore certainly feels like his very best friend every time they are on-screen together.

Whenever they're in the same scene, Sandler and Barrymore are always messing with each other — or they're missing with everyone else around them. They tease and poke at each other in every film like a pair of best friends. In The Wedding Singer, there's a scene where a wedding photographer mistakes them as a couple (they're not a couple yet). Instead of being embarrassed, the two jump into this weird, absurd improv scene where they pretend to be siblings with a very, very interesting relationship. The look of shock on the photographer is as extreme as the laughs that people experienced seeing this because the pair are being utterly mischievous and rascally. Even though Sandler is the SNL alum, Barrymore never misses a beat and keeps up with him joke-for-joke. In 50 First Dates, Barrymore is able to match Sandler's humor yet again, even though she's essentially playing a character who doesn't even have the memory of their past to build on. And even almost 20 years after their first film, Barrymore is just as funny as Sandler in Blended as she jokes around with her kids in their wacky adventures. Even in their most sincere moment before their first kiss, she takes a moment to tease him as payback for something he did earlier in the movie.

Barrymore's comedic style perfectly complements Sandler's. She brings her own brand of girlish charm that pairs with his boyish mischief. And whenever Sandler maxes out on absurdity, she's right there with him, as they constantly build on each other's jokes with full commitment and reckless abandon. Though her character might be more straight laced in the beginning of their movies, they always ultimately love fun and truly enjoy the company of Sandler's characters. Barrymore doesn't just keep up with Sandler's jokes, often times she pushes them even further than he intended, and it's a joy to see.

That complimentary humor only serves to maximize Sandler's own performances. He's allowed to be as goofy and slapstick as he wants because Barrymore bounces off of him; his jokes are much less cringey because his scene partner is actively enjoying them as well. He's able to go as extreme as he wants, but he still stays palatable because there's no discomfort in the joke. There's incredible power in saying "yes and" to a co-star's jokes, and Barrymore encourages Sandler to be as daring as he wants to be.

What's the secret to all that on-screen camaraderie? It's their actual friendship off-screen. When interviewed about how their lives have changed since their first film together, they mention how they've grown up and started their own families. But more importantly, Sandler professed that, "No matter what’s going on, I’m always pulling for Drew, and she’s the same way, whenever I’m doing something. I know she’s pulling for me." These two are genuine friends who genuinely care about each other, and the end results speak for themselves.

Adam Sandler and Drew Barrymore Have Effortless Romantic Chemistry

Drew Barrymore as Julia and Adam Sandler as Robbie smiling in 'The Wedding Singer.'
Image via New Line Cinema

For as funny as the two are, that's not the complete picture of Adam Sandler at his best. There's that aforementioned heart and sincerity that needs to be put on screen which Barrymore pulls out of him in each of their performances. They have played three different couples in three different decades: Robbie and Julia, Henry and Forgetful Lucy, Jim and Lauren. In each of these films, there's a through line on the type of relationship and connection that the two depict. Barrymore's characters always fully love and accept Sandler's characters for who they truly are, without needing him to change. Sandler's characters always love Barrymore's characters with complete devotion that shows in his extravagant and committed actions.

In The Wedding Singer when a distraught Robbie sings his emo anthem titled "Somebody Kill Me Please," Julia smiles and genuinely likes it. In 50 First Dates, since Lucy's short-term amnesia prevents her from remembering her life, Henry makes a daily video recap for her to watch every morning to catch her up-to-date on her life. In Blended, Jim and Lauren are overworked parents who feel that they have to provide for their children 99% of the time and can only want things 1% of the time. And for that 1%, they choose each other. At every opportunity that their characters show who they truly are, the other accepts them no matter how unhinged or difficult they may be.

After watching even a single one of Sandler's movies with Barrymore, it would be a disservice to say he could not act sincere and genuine. Whether he is serenading her on a plane, comforting her with a video, or even co-raising her children with the actual comfort of a real dad, Sandler is able to be a grounded and comforting figure even through all his humor and levity. He approaches these moments with serious commitment and devotion. Even when he makes a joke in those times of intimacy, it's for a greater purpose. He's not saying a joke because it's a comedy and he needs to be funny at every moment. He cracks a joke because sometimes you just need a friend to make you smile when you're feeling down. Sandler brings his acting A-game alongside Barrymore, bringing such heartfelt sincerity to his role that makes his characters feel more realistic because of their humor, not in spite of it. That combination of comforting realism with witty enjoyment is the full Adam Sandler experience.

If none of this was enough to convince you, perhaps the man himself can seal the deal. When asked if he could choose one movie to represent his entire career, Sandler definitively chose The Wedding Singer, his first of many amazing performances alongside Drew Barrymore. The person who best complements and enhances Sandler's best features is Barrymore. So if you want the very best that the wedding singer can offer, put one of his best movies alongside his best co-star and laugh along with the most genuinely funny and kind performances Adam Sandler has ever put on the silver screen.