The Strange Sadness of Adam Sandler Movies

Adam Sandler is known, not-undeservedly, as a goofball. It is cliche to say that comedy can hide great pain — look no further than Chris Farley or Mitch Hedberg — but Adam Sandler is not necessarily known in the popular consciousness as a very deep or complicated actor outside of a few outlying roles (Punch-Drunk Love and Reign Over Me come to mind as overtly drama-based Sandler roles). A combination of a quiet personal life, press-shyness, outlandish screen presence, and unfriendly criticism have denied Sandler his proper due as a nuanced creator of comedy who embraces subtle but heavy emotional themes. Especially in films in which Sandler has a writing or production credit, powerful motifs recur. Sandler, more than some other comics, was willing to work somber, personal themes into his movies.

Sandler’s characters waste no time garnering pity; on screen, Sandler embodies the self-deprecating schmuck. Sandler’s characters reach rock-bottom quickly as he lashes out at those around him, anger functioning as a plea for help as he spirals the drain. This temper is often borne out of terrible emotional pain residing inside of Sandler’s characters. Crucially for audience sympathy, these anger-causing issues often seem to be out of Sandler’s control — great cosmic injustices— in fact, the lingering death of a family member seems to be a weirdly-recurring theme.

Emotional baggage is introduced early in Sandler’s films and builds a sense of tension and irony in the audience — only we, the viewer, know what drives Sandler’s characters to self-defeating tantrums. In this, there is a profound sadness: the character can’t share his pain with anybody; we watch as he digs himself further into the hole of his own sorrow and anger. Like a misbehaving puppy, Sandler characters seem to find a sweet, sentimental spot in the viewer’s heart through their endearing wiliness.

For me, the emotional themes in Sandler films (especially those dealing with family dynamics) are strangely magnetic in how they mirrored my feelings growing up a child of divorce. The unique growing pains of childhood are embedded deep into Sandler’s characters; Sandler has admitted in interviews that he draws on his childhood when creating characters or plots. In retrospect, Sandler films have come to define certain periods of my childhood. Watching many of these movies again, I can identify the subtle emotional undercurrents that I didn’t notice as a child; with hindsight, I can put into words many of the feelings I couldn’t express years ago and explain why some Sandler films have such a unique emotional resonance. And since I cried while watching (more than) one of these, I have listed the saddest moment of these films, Sandler’s major emotional works.

Going Overboard (1989)

Going Overboard, Sandler’s full-length debut, is a tale about the struggle of stand-up comedy and its effect on the ego, parlaying Sandler’s come-up as a nervous, stuttering comic struggling to overcome his low-self confidence into a wacky story about a cruise ship full of beauty queens, King Neptune, and the dictator Noriega. The film plays as a bunch of loosely-flowing bits interjected with fourth-wall-breaking commentary from Sandler — essentially just a bunch of stand-and-talk Saturday Night Live-style vignettes with the story delivered via narrator. There are flashes of Sandler’s SNL brilliance, especially in scenes involving a rocker named Croaker and his song “I Want To Slap Your Cat” (a hilarious “Highway To Hell” crib).

The skit-like nature of Going Overboard leaves it bereft of any of the character development and urgency that would make later Sandler movies emotionally gripping, but still this film provides a window into Sandler’s psyche and developing confidence as a stand-up. Most telling are the dream sequences, in which Sandler alternately envisions the successful stand-up sets he so desires and terrible, psychedelic catastrophes that reveal his paralyzing anxiety of performance. But even when the jokes are hitting, they’re self-deprecating (a sample: “My mom said, ‘Shecky, you have to marry a girl with the same beliefs as your family’ — I said, ‘why would I marry someone who thinks I’m a schmuck?’”). Worth noting also is the theme of “the power of laughter,” which Shecky uses to dispose of two would-be assassins at the end of the movie — later Sandler movies faced tragedy and laughter head-on, implicitly endorsing the power of comedy to heal tragedy.

SADDEST MOMENT: In a dream sequence, Shecky’s mom, played by a man, says (apropos of nothing) “I knew you were suicidal. I knew it! You’re gonna die from this, Shecky!”

Happy Gilmore (1996)

The film begins with the great tragedies of Sandler’s titular character’s life: his mom leaves him and his father alone, his father dies from a hockey puck to the head, his grandmother’s house is foreclosed, and his girlfriend dumps him. From then, as an audience, it’s easy to sympathize with Happy when he gets into numerous unnecessary fights — he said in the opening, “after my dad passed, I had a short fuse” (plus, he and his dad’s favorite hockey player was a notorious fighter, so he wants to make his dad proud).

Happy Gilmore showcases the fast temper that Sandler brought to many of his characters. Looking back, I see part of my younger self in Happy — part due to my tendency to try to hit the golf ball as far as he did and part from my short temper. I didn’t know why I had so much anger at the time; growing up in shared custody of two divorced parents (even though mine handled it extremely well) was confusing. I felt different from other kids sometimes, like I didn’t fit in with my strange family. Happy’s anger came from his inability to make it as in hockey, the only place he felt he fit in and a sport that caused the split of his family and death of his father.

Sandler’s explosive outbursts in this movie came from a real place in his childhood as well. In an interview with Harvard’s Crimson, he stated this about the anger problems of his characters: “In real life, I do have a bit of that problem…Sometimes when I’d snap in my house growing up, it would make my dad laugh. Or sometimes, he’d smack me.” Sandler’s relationship with his father often comes up in interviews, and his responses vary from casually mentioning abuse and his father not approving of his comedy to respectful praise. Coincidentally, father figures in Sandler movies are often a source of complex emotions. Happy Gilmore and other Sandler movies show the pain of childhood bubbling up — Sandler would draw upon this for his more magnetic performances later in his career.

(a clip of an interview with Adam Sandler during his Happy Gilmore press run where he talks about his dad)

SADDEST MOMENT: Happy’s mom moves to Egypt to be 1500 miles from the nearest hockey rink.

The Wedding Singer (1998)

In Sandler’s first lead role that he didn’t write himself (and his first opposite of Drew Barrymore), he plays a down-on-his-luck 80's wedding singer named Robbie Hart in a doomed engagement that has fallen in love with an engaged server he works with. This role was Sandler’s most serious to date, eschewing much of his oddball humor for self-loathing, drunken quips.

The miserable, failed rocker persona that Sandler projects here is one of his straightest play on the depression that subtly shows itself in some of his other films. The pain and hopelessness that plagued Robbie Hart after the dissolution of his engagement were beautifully portrayed by Sandler; perhaps not accidentally, this performance coincided with the death of Sandler’s close friend Chris Farley. The despair for Robbie wasn’t permanent, of course — he eventually ended up with his dream girl. The sudden swing of emotion at the end of the movie was reflected by Sandler in an interview about Farley’s death: “What I try to do is just know that I’ll get past the down times, and the good times are going to come again.” We would see Sandler characters reflecting this tenet in later movies — hitting sudden luck to turn their fortunes, counting on the ultimate good of the universe and the promise of good things coming to people who have struggled.

SADDEST MOMENT: Sandler and Barrymore both deciding to express their feelings for each other only for both of them to give up, resigning themselves to their unhappy relationships.

The Waterboy (1998)

In The Waterboy, Sandler works through the humiliation he experienced in his childhood for his heavy stutter. He plays Bobby Boucher, a coddled mama’s boy with a speech impediment who has a passion for being the waterboy for football teams, which causes him heavy torment. Sandler channels his anger toward boyhood bullies through Bobby, who becomes a hard-hitting linebacker, using his anger to motivate himself to superhuman strength.

The emotional core of this story comes from the mother-son relationship between Bobby and a domineering mom played by the always-terrifying Kathy Bates. Bobby’s mom doesn’t allow him contact with the outside world for fear that he will be made a fool for his speech impediment and simple ways. Sandler mulls on being overprotected, like he was by his mom who feared bullying for his stutter; Bobby’s mom tells him lies about the outside world being dangerous to keep him from leaving the house. After being left by Bobby’s dad, Bobby’s mom was clinging to the only thing she had left — her child, who she didn’t want to desert her for football.

Growing up in a man-free household, my mom was, of course, super-protective of me (I also had a stutter that caused me anxiety, though I didn’t get teased for it). I grew to learn to ask my dad for things that my mom would freak out about — R-rated movies, video games, BB guns — and started to resent the lack of freedom I had with my mom. But in hindsight, I can see that my mom was crazy-protective out of love, just like Bobby’s mom — she only lied because she didn’t want to lose Bobby. Kathy Bate’s at-first scary performance of a strict mother turns heartwarming when you consider her motivations. Of course, like Bobby and Sandler himself, I learned to love the times my mom was overbearing — it was her showing her love for me and fear that something bad could happen to her baby.

SADDEST MOMENT: Bobby cries when his new college professor tells him that his mama’s country wisdom is wrong.

Big Daddy (1999)

Riding off of an adorable performance by Cole and Dylan Sprouse as Julian, a 5-year-old taken in by the recent bachelor Sonny (Sandler), Big Daddy played with family dynamics more than any previous Sandler film. While previous films had hinted toward themes of fatherhood, this one doubled down. Sandler once said that he’s gets payed to do stuff his dad would stop him from doing — his father would often chastise him for his foolish ways. Similarly, Sonny experiences paternal disapproval for living off an injury settlement instead of finishing a law degree. Determined to be the “fun dad” his father never was, Sonny lets Julian run wild. Sandler in real life had a permissive streak with his little nieces and nephews, saying “ I always used to teach them how to curse and spit” — things his father frowned upon.

As a child, Sonny’s whimsical approach to single fatherhood resonated with me. Like Sonny, my dad was a recently-single Syracuse grad working to raise a young child. Sonny’s silliness reminded me so much of my own father. I wanted so much to have fun with my dad the way Julian did with Sonny — and we often did, my dad taking me to McDonald’s breakfast and teaching me gross tricks like Sonny did with Julian (and letting me watch movies like this when my mother wouldn’t!). But like Sonny and Julian, me and my dad had rough times as well — single fatherhood is stressful and it’s impossible for a person to be a perfect father at all times, even when they want to be. There were times when we were moving around houses or I had to stay at school until 7 when my dad could pick me up — it wasn’t the fantasy that it seems in the first half of Big Daddy. In a sense, though, Big Daddy was the ideal I looked to when the unpleasant realities of single parenthood hit. When I watch this movie now, I look back with a sense of warmth toward my dad and all he did to make a hard situation better; Sonny is my favorite ever on-screen dad because he made me feel better about the difficulties of my situation.

SADDEST MOMENT: Julian gets taken away from Sonny.

Punch-Drunk Love (2002)

Sandler, the self-proclaimed “youngest and dumbest” of his family, plays Barry Egan, the nervous-wreck laughing stock of his seven sisters, who torment him into an impenetrable shell of shyness. Sandler draws from his personal life for this character, channeling the uncertainty of being the oddball of the family. The perpetual fear of disapproval that Barry shows around his family again reflects Sandler’s trouble with his father on his path to comedy. This anxiety is elevated by Paul Thomas Anderson’s directing and Jon Brion’s score, which serve to highlight the nervous energy that Sandler’s character radiates. Anderson and Brion make this the outright moodiest audiovisual Sandler flick, but the hook of this movie is Sandler’s magnetic performance. Barry’s heightening despair allows him to start not caring about his sisters’ judgement and frees him from his self-created prison of shyness. Just as Barry would have given up, he is saved by love, underlining Sandler’s belief that great sadness and depression has a way of leading to great happiness.

SADDEST MOMENT: Barry breaks the sliding glass door when his family won’t stop harassing him.

Eight Crazy Nights (2002)

This Sandler film leans into the pain of dead parents more than any other as Davey Stone (Sandler) turns to debauchery from a promising childhood after the tragic death of his mom and dad. After nearly throwing his life down the drain, he learns to let go of the pain that caused him to be an angry alcoholic and embrace living to help others through a Hanukkah miracle.

For me, this movie reminds me of my stepdad. I started watching this movie when he was first teaching me and my brother about Hanukkah (he’s a Jew, we were raised Catholic); as he taught us more about his religion, we would watch Eight Crazy Nights with him and start to understand more of the jokes. As he got tired of our a capella renditions of “The Chanukah Song”, he bought the CD so we could sing along in the car. My stepdad actually just texted me about “The Chanukah Song” a couple days ago; Eight Crazy Nights became a symbol of our relationship — the coziness of Sandler movies make them easy to bond over and form fond memories.

SADDEST MOMENT: Davey’s dead parents sing to him.

50 First Dates (2004)

The emotional drive of the second Sandler and Drew Barrymore picture comes from the chemistry between the two leads — this is probably Sandler’s best in-love performance. Sandler’s character isn’t the focus here though, he’s merely support; Barrymore dazzles as a memory-loss patient who has to relearn her whole world every day. Although as emotionally gripping as any Sandler flick, it relies less on Sandler’s typical down-up character arc.

SADDEST MOMENT: Drew Barrymore has to wake up every day and not know anything about her years-old daughter.

Click (2006)

This is the one where Sandler decided he wanted to make everybody cry (and he did). This essentially plays like a Sandler movie in reverse — a content man comes upon something that brings him unimaginable pain and hopelessness. Instead of highlighting the light that lies ahead in times of darkness, Sandler slowly disassembled a happy family to devastating effect. This was Sandler’s first concession to what he proposed in Going Overboard about the power of laughter — maybe humor can’t solve everything, and maybe tragedy is unavoidable and meaningless. Putting aside the last-second twist, however, Click didn’t foreground any emotionally-complex material — most of the first half is fart and boob jokes (even more than usual for Sandler fare). But that last act really punches you in the gut, though, and that’s due to Sandler’s trademarked lovable screwball demeanor that’s tinged with the slightest sense of sadness and self-loathing.

SADDEST MOMENT: You’re a monster if you didn’t shed a tear when Sandler died.

Reign Over Me (2007)

Reign Over Me, while the only non-starring role for Sandler on this list, is his most straightforward dramatic role. This is Sandler stripping goofball comedy completely from his repertoire and retreating into the paralyzing numbness that comes with great loss. Playing Charlie Fineman, a man who is left without any family after losing his parents in grade school and his wife and 3 daughters on 9/11, Sandler is an emotional hermit who can’t open up to anyone about his unimaginable pain nor face it himself, drowning his mind out with constant music from his headphones. He brings with him the nervous affectations of his Little Nicky and Waterboy characters, but this time it is played without humor — the only reaction to Charlie is pity. Charlie plays as foil to Sandler’s previous characters, who relied on comedy and staying in their comfort zones, waiting for happiness to find them; only when Charlie gives up his childish antics to confront his pain are his problems bettered. Healing isn’t immediate — even confronting his pain for the first time, Charlie nearly commits suicide; unlike other Sandler characters who were the beneficiaries of deus ex machina, Charlie only finds help by facing his demons head-on and welcoming the pain. As with Click, the maxims of Sandler’s older movies are inverted, seeking a more mature perspective on the topics of loss and depression.

SADDEST MOMENT: Wandering around his apartment alone, Charlie hallucinates that his dead family is still there with him.