Adam Sandler’s Career: From ‘Going Overboard’ to ‘Happy Gilmore 2’

Adam Sandler is one of the most successful and recognizable comedians of his generation. Starting his career as a stand-up comic and a cast member on ‘Saturday Night Live’, he quickly developed a unique brand of humor that resonated with audiences worldwide. His early films established a persona of a lovable, man-child character who often found himself in absurd situations, usually involving yelling and slapstick comedy. Through his production company, Happy Madison Productions, he has created a cinematic empire, often working with a recurring cast of friends.

Over the years, Sandler’s career has evolved in surprising ways. While he continues to produce the comedies that made him famous, he has also taken on challenging dramatic roles that have earned him critical acclaim. This has revealed a depth and range that many of his early critics did not expect. From low-brow comedies to heartfelt dramas and even science fiction, Adam Sandler has built a diverse and incredibly durable career, proving he is far more than just a funny guy.

‘Going Overboard’ (1989)

Adam Sandler made his film debut in ‘Going Overboard’ playing Schecky Moskowitz. The story follows Schecky, a struggling comedian who works on a cruise ship. He desperately wants to become the ship’s main comedy act but faces competition and a series of mishaps, including the ship being attacked by terrorists during a Miss Universe pageant.

The movie was a low-budget production and was not successful upon its initial release. However, after Sandler became a major star, the film was re-released to capitalize on his fame. It is often viewed today as a curiosity piece, offering a very early glimpse of the comedic style and on-screen persona that Sandler would later refine.

‘Shakes the Clown’ (1991)

In this dark comedy, Sandler played a minor role as Dink the Clown. The film, directed by and starring Bobcat Goldthwait, is set in the fictional town of Palukaville, where clowns are a downtrodden, alcoholic subculture. The story follows Shakes, a birthday-party clown who is framed for murder and must clear his name.

Sandler’s role as Dink is small, but his presence in the cult film is notable. He is part of the strange and chaotic world of clowns depicted in the movie. It was another early role that placed him alongside other comedians and showed his willingness to participate in unconventional and edgy projects before he became a household name.

‘Coneheads’ (1993)

Sandler appeared in ‘Coneheads’ as Carmine Weiner. The film is based on the popular ‘Saturday Night Live’ sketch and follows the Conehead family, aliens with cone-shaped heads who try to assimilate into suburban American life. Carmine is a nerdy character who becomes an informant for an INS agent trying to deport the Coneheads.

The role was a supporting part that capitalized on the nerdy, awkward persona Sandler sometimes used in his ‘SNL’ sketches. Working with fellow ‘SNL’ cast members like Dan Aykroyd and Jane Curtin, the film was a natural transition from television to the big screen. It helped increase his visibility in Hollywood comedies.

‘Airheads’ (1994)

In ‘Airheads’, Sandler played Pip, the drummer of a struggling rock band called The Lone Rangers. Alongside his bandmates, played by Brendan Fraser and Steve Buscemi, he hijacks a radio station with toy guns in a desperate attempt to get their demo tape played on the air. What starts as a simple plan quickly escalates into a city-wide hostage situation.

Pip is a simple-minded and sweet character who provides much of the film’s comic relief. The movie became a cult classic, remembered for its fun premise and snapshot of 90s rock culture. Sandler’s performance showcased his ability to play a goofy but endearing character, a key part of his emerging comedic identity.

‘Mixed Nuts’ (1994)

Sandler had a supporting role as Louie Capshaw in the holiday black comedy ‘Mixed Nuts’. The film, directed by Nora Ephron, takes place on Christmas Eve at a crisis hotline center in Venice, California. It follows the chaotic interactions between the staff and the various troubled people who call or visit them throughout the night.

Sandler’s character, Louie, is a lonely man who plays the ukulele and sings goofy songs. Though the film received mixed reviews, the role allowed Sandler to work with a talented ensemble cast that included Steve Martin and Madeline Kahn. It was another step in building his film career outside of his ‘SNL’ fame.

‘Billy Madison’ (1995)

This film marked Adam Sandler’s first starring role, playing the titular Billy Madison. He is the lazy and immature 27-year-old heir to a hotel fortune. To prove to his father that he is capable of taking over the family business, Billy agrees to repeat all 12 grades of school in 24 weeks.

‘Billy Madison’ was a huge success and established the core of Sandler’s comedic persona. The film is filled with the silly, absurd, and often loud humor that would define his early career. It became a 90s comedy classic and proved that Sandler could carry a movie as the leading man.

‘Happy Gilmore’ (1996)

Sandler starred as Happy Gilmore, a hot-tempered but unsuccessful hockey player who discovers he has an incredible talent for golf. He joins the professional golf tour in an attempt to win enough money to save his grandmother’s house from foreclosure. His aggressive behavior and unorthodox style clash with the traditional, stuffy world of golf.

‘Happy Gilmore’ was another massive hit that solidified Sandler’s status as a top comedy star. The film is one of his most beloved and quoted movies, combining slapstick, sports, and a surprising amount of heart. The character of Happy, with his explosive anger and powerful swing, became an iconic figure in comedy.

‘Bulletproof’ (1996)

In ‘Bulletproof’, Sandler co-starred with Damon Wayans. He played Archie Moses, a small-time criminal who is befriended by an undercover cop named Jack Carter. When Archie accidentally shoots Jack in the head, the two become bitter enemies, but they are later forced to work together when they are targeted by a powerful drug lord.

This film was a departure from his usual solo comedies, placing him in an action-comedy duo. While not as critically or commercially successful as his other films from the era, it showed Sandler experimenting with a different genre. The movie relied on the chemistry between its two leads in a classic buddy-cop formula.

‘The Wedding Singer’ (1998)

Sandler played Robbie Hart, a wedding singer in the 1980s who is left at the altar by his own fiancée. Heartbroken, he becomes bitter and cynical about love and marriage until he befriends a waitress named Julia Sullivan, played by Drew Barrymore. The two develop feelings for each other, even though Julia is engaged to another man.

‘The Wedding Singer’ was a huge success and marked a turning point in Sandler’s career. It was his first romantic comedy and showed a sweeter, more charming side to his on-screen persona. The chemistry between Sandler and Barrymore was highly praised, and the film’s 80s nostalgia made it a hit with audiences.

‘The Waterboy’ (1998)

In ‘The Waterboy’, Sandler played Robert “Bobby” Boucher Jr., a socially inept, stuttering water boy for a college football team. After being fired, he takes a job with a losing team and discovers that he can channel his years of pent-up anger into becoming a ferocious and unstoppable tackler.

The film was a massive box office success and remains one of Sandler’s most popular movies. The character of Bobby Boucher, with his distinct voice and gentle nature, became iconic. ‘The Waterboy’ perfected the formula of a good-hearted Sandler character overcoming bullies to become a hero.

‘Big Daddy’ (1999)

Sandler starred as Sonny Koufax, a lazy law school graduate who has spent his life avoiding responsibility. In an attempt to impress his girlfriend and prove he can be mature, he adopts a five-year-old boy named Julian. Sonny’s unconventional and irresponsible parenting methods lead to both comedic and heartwarming situations.

‘Big Daddy’ was another box office hit, continuing Sandler’s successful run in the late 90s. The film combined his signature slacker comedy with a story about fatherhood and growing up. It showcased his ability to blend humor with genuine emotion, a combination that audiences loved.

‘Little Nicky’ (2000)

In ‘Little Nicky’, Sandler played the title character, one of Satan’s three sons. Nicky is a sweet and gentle demon who is sent to Earth to stop his two evil brothers from creating a new hell in New York City. On his mission, he learns about the human world and tries to save his father and prevent the apocalypse.

This film was a high-concept fantasy comedy that received mixed reviews and was not as commercially successful as his previous work. Sandler played a physically contorted character with a speech impediment, which was a polarizing choice for some viewers. The movie is remembered for its bizarre premise and star-studded cast of cameos.

‘Punch-Drunk Love’ (2002)

Sandler took on a dramatically different role in ‘Punch-Drunk Love’, directed by Paul Thomas Anderson. He played Barry Egan, a lonely and socially anxious novelty-item supplier who is prone to fits of violent rage. His life changes when he falls in love with a woman and simultaneously gets blackmailed by a phone-sex line.

This role earned Sandler widespread critical acclaim and a major award nomination. His performance was a revelation for critics, showcasing a vulnerability and emotional depth that was unseen in his comedies. The film proved that Sandler was a talented dramatic actor capable of delivering a powerful and nuanced performance.

‘Mr. Deeds’ (2002)

In this remake of a classic film, Sandler played Longfellow Deeds. He is a kind, small-town man who inherits a massive media empire from a distant uncle he never knew. When he moves to New York City to manage his new fortune, his simple values clash with the cynical and greedy corporate world.

‘Mr. Deeds’ marked a return to the familiar good-guy comedy formula that had proven successful for Sandler. The film was a commercial hit, with audiences responding to the story of a humble man who stays true to his roots despite immense wealth. It reinforced his image as a star of feel-good comedies.

‘Eight Crazy Nights’ (2002)

‘Eight Crazy Nights’ is an animated musical holiday film in which Sandler voiced three main characters: Davey, Whitey, and Eleanor. The story follows Davey Stone, a bitter and angry man who is forced to do community service as a youth basketball referee during Hanukkah. He is supervised by Whitey, an eccentric and kind-hearted old man.

This was Sandler’s first lead role in an animated film, and it was a passion project for him. The movie is a mix of his typical crude humor and a surprisingly serious story about loss and redemption. It has since become a cult classic for its unique place as a Hanukkah-themed holiday movie.

‘Anger Management’ (2003)

Sandler starred as Dave Buznik, a timid and non-confrontational man who is wrongly sentenced to an anger management program after a misunderstanding on an airplane. The program is run by an aggressive and unorthodox therapist, Dr. Buddy Rydell, played by Jack Nicholson. Buddy’s bizarre methods make Dave’s life chaotic.

Pairing Sandler with a legendary actor like Jack Nicholson was a major draw for audiences, and the film was a box office success. The premise allowed Sandler to play the straight man to Nicholson’s over-the-top character. It was a high-concept comedy that delivered on the fun of seeing two huge stars share the screen.

’50 First Dates’ (2004)

In ’50 First Dates’, Sandler reunited with Drew Barrymore. He played Henry Roth, a veterinarian in Hawaii who falls for a woman named Lucy Whitmore. He soon discovers that Lucy suffers from short-term memory loss as a result of a car accident and can’t remember anything from the previous day. Henry must make her fall in love with him again every single day.

The film was a huge commercial success and is considered one of the best romantic comedies of the 2000s. The unique premise allowed for both comedic and genuinely touching moments. The undeniable chemistry between Sandler and Barrymore was once again the heart of the film, making it a fan favorite.

‘Spanglish’ (2004)

Sandler took on another dramatic role in ‘Spanglish’, directed by James L. Brooks. He played John Clasky, a successful chef and devoted family man whose life is changed when his family hires a Mexican immigrant named Flor as their housekeeper. The film explores themes of family, culture, and communication.

His performance was praised by critics, who noted his warmth and subtlety in a more grounded, realistic role. Sandler played a sensitive and conflicted character dealing with a struggling marriage and the challenges of parenting. The film further demonstrated his ability to excel in dramas as well as comedies.

‘The Longest Yard’ (2005)

In this remake of the 1974 film, Sandler played Paul Crewe, a disgraced former professional football quarterback. After a drunk driving incident, he is sent to a tough prison. The warden forces him to assemble a team of inmates to play a football game against the prison guards.

‘The Longest Yard’ was a major box office hit. The film blended comedy and sports, two genres where Sandler had previously found great success. Starring alongside Chris Rock and a host of former professional football players and wrestlers, the movie was an entertaining ensemble piece that appealed to a wide audience.

‘Click’ (2006)

Sandler starred as Michael Newman, an overworked architect who neglects his family in pursuit of a promotion. He gets a universal remote control that allows him to fast-forward, rewind, and pause his own life. At first, it seems like the perfect tool, but he soon learns that skipping through life’s challenges has serious and heartbreaking consequences.

‘Click’ was a unique film in Sandler’s career because it blended his signature comedy with a surprisingly emotional and dramatic story about family and regret. While it starts as a typical high-concept comedy, the second half of the movie takes a much darker and more serious turn. The film was a commercial success and resonated with audiences for its powerful message.

‘Reign Over Me’ (2007)

In ‘Reign Over Me’, Sandler delivered one of his most acclaimed dramatic performances. He played Charlie Fineman, a man whose wife and daughters were killed in the 9/11 attacks. Five years later, he is a broken man, completely shut off from the world, until he reconnects with his old college roommate, who tries to help him heal.

Sandler’s portrayal of a man consumed by grief was praised as deeply moving and powerful. He completely disappeared into the role, showing a level of dramatic depth that surprised many. The film cemented his reputation as a versatile actor who could handle intensely serious material with incredible skill and sensitivity.

‘I Now Pronounce You Chuck & Larry’ (2007)

Sandler co-starred with Kevin James in this comedy. He played Chuck Levine, a womanizing firefighter who convinces his best friend and fellow firefighter, Larry Valentine, to pretend to be a gay couple. They do this so Larry can receive domestic partner benefits for his children. Their plan gets complicated when they are investigated for fraud.

The film was a big box office success but was controversial for its humor and its handling of LGBTQ+ themes. Despite the criticism, the movie’s central message was one of tolerance and acceptance. It was another successful pairing for Sandler with Kevin James, who would become a frequent collaborator.

‘You Don’t Mess with the Zohan’ (2008)

Sandler played Zohan Dvir, an Israeli counter-terrorist commando who fakes his own death so he can move to New York City and pursue his dream of becoming a hairdresser. He gets a job at a salon and becomes famous for his unorthodox and flamboyant style. His past catches up with him when he is recognized by a Palestinian taxi driver.

This over-the-top action-comedy was co-written by Sandler, Robert Smigel, and Judd Apatow. The film is known for its absurd premise and slapstick humor. ‘You Don’t Mess with the Zohan’ was a commercial success, with audiences enjoying the silly and high-energy performance from Sandler.

‘Bedtime Stories’ (2008)

In this family-friendly fantasy-comedy, Sandler played Skeeter Bronson, a hotel handyman whose life changes when the imaginative bedtime stories he tells his niece and nephew start to magically come true. He tries to use the stories to improve his own life, but the children’s unexpected additions to the tales lead to chaotic results.

This was Sandler’s first leading role in a major studio family film, marking a deliberate move into more family-oriented entertainment. The movie was a holiday season hit, appealing to both children and adults with its charming premise and lighthearted humor. It showed a softer side of Sandler’s comedy, suitable for all ages.

‘Funny People’ (2009)

Sandler reunited with writer-director Judd Apatow for ‘Funny People’. He played George Simmons, a hugely successful but lonely and self-absorbed comedian and movie star who is diagnosed with a terminal illness. Believing he has little time left, he tries to mend the broken relationships in his life and takes on a young, struggling comedian as his assistant.

The film is a dramedy that closely mirrors parts of Sandler’s own career, exploring the worlds of stand-up comedy and Hollywood fame. His performance was critically acclaimed for its honesty and vulnerability. He expertly balanced comedy with the serious drama of a man confronting his own mortality and regrets.

‘Grown Ups’ (2010)

‘Grown Ups’ featured an all-star cast of Sandler’s real-life friends, including Chris Rock, Kevin James, David Spade, and Rob Schneider. They play five childhood friends who reunite for a Fourth of July weekend after their former basketball coach passes away. They spend the weekend at a lake house with their families, reliving their glory days and dealing with the realities of adulthood.

The film felt like a fun vacation with friends, and that relaxed, improvisational energy was a huge draw for audiences. Despite negative reviews from critics, ‘Grown Ups’ was an enormous box office success. It kicked off a successful franchise and became one of the most popular films of Sandler’s career.

‘Just Go with It’ (2011)

In this romantic comedy, Sandler played Danny Maccabee, a successful plastic surgeon who pretends to be in an unhappy marriage to attract women. When he finally meets the woman he thinks is the one, he enlists his loyal assistant, Katherine Murphy, played by Jennifer Aniston, to pose as his soon-to-be-ex-wife.

The film was a major commercial hit, largely due to the fantastic chemistry between Sandler and Aniston. The movie is a classic romantic comedy with a modern twist, filled with funny situations and charming performances. It became another successful entry in Sandler’s catalog of popular romantic comedies.

‘Zookeeper’ (2011)

Sandler had a voice role in ‘Zookeeper’, which starred his frequent collaborator Kevin James. The film is about a kindhearted zookeeper who is unlucky in love. To help him win the heart of the woman he loves, the zoo animals break their code of silence and reveal they can talk, offering him their wild advice on dating.

Sandler voiced Donald the Capuchin Monkey, one of the main animal characters who helps the zookeeper. His distinctive voice was a perfect fit for the funny and mischievous monkey. The family-friendly comedy was a commercial success, and his voice work added star power to the ensemble cast.

‘Jack and Jill’ (2011)

In ‘Jack and Jill’, Sandler took on the challenge of playing two roles: Jack Sadelstein, a successful advertising executive, and his annoying, needy identical twin sister, Jill. The film follows the chaos that ensues when Jill comes to visit Jack’s family for Thanksgiving and refuses to leave.

The film is widely considered to be one of the worst movies ever made and was universally panned by critics. It famously received awards that celebrate the worst in film. Despite the terrible reviews, the movie was still commercially successful, demonstrating the loyalty of Sandler’s fan base.

‘That’s My Boy’ (2012)

Sandler starred as Donny Berger, who, as a teenager, fathered a son with his teacher. Years later, Donny is an irresponsible wreck, while his son, now a successful man on the eve of his wedding, has changed his name to avoid his past. Donny shows up unannounced, hoping to reconnect and get money to pay off his taxes.

This film was a hard R-rated comedy, a return to the more raunchy and adult humor of Sandler’s early career. The movie received overwhelmingly negative reviews and was a box office disappointment. It was a rare commercial misstep for Sandler at the time.

‘Hotel Transylvania’ (2012)

Sandler voiced the iconic character of Count “Drac” Dracula in the animated film ‘Hotel Transylvania’. In this version of the story, Dracula is the overprotective father of a teenage daughter, Mavis. He builds a lavish, monster-only hotel as a safe haven for her, but his world is turned upside down when a human unexpectedly checks in.

The film was a massive global success, praised for its clever humor and vibrant animation. Sandler’s performance as Dracula, using a comically exaggerated accent, was a highlight. The movie launched a hugely successful franchise, becoming one of the most beloved and profitable projects of his career.

‘Grown Ups 2’ (2013)

Sandler and his friends returned for ‘Grown Ups 2’. In the sequel, Sandler’s character, Lenny Feder, has moved his family back to his hometown to be with his friends and their families. The film follows their adventures over the course of a single day, culminating in a massive 1980s-themed party.

Like its predecessor, the sequel was heavily criticized by critics for its lack of a plot and its reliance on simple gags. However, it was once again a huge box office success. The film proved that audiences simply enjoyed seeing Sandler and his friends having fun on screen, regardless of the story.

‘Blended’ (2014)

‘Blended’ marked the third collaboration between Adam Sandler and Drew Barrymore. They play two single parents who, after a terrible blind date, find themselves and their children stuck together on a vacation at a luxurious African safari resort. The two families are forced to share a suite and participate in a series of family-bonding activities.

While it didn’t reach the same level of success as ‘The Wedding Singer’ or ’50 First Dates’, the film was a modest hit. The undeniable chemistry between Sandler and Barrymore was again the main attraction. The movie is a sweet family comedy that appealed to fans of their previous pairings.

‘Men, Women & Children’ (2014)

Sandler appeared in the ensemble drama ‘Men, Women & Children’, directed by Jason Reitman. The film follows the interconnected stories of a group of high school students and their parents in a small town. It explores how the internet has changed their relationships, communication, and self-image.

Sandler played Don Truby, a man in a loveless marriage who, along with his wife, seeks out affairs online. It was another serious, dramatic role that allowed him to work within a talented ensemble cast. The film received mixed reviews but was praised for its timely themes and strong performances.

‘The Cobbler’ (2014)

In the fantasy comedy-drama ‘The Cobbler’, Sandler played Max Simkin. He is a fourth-generation cobbler in New York City who is bored with his simple life. He discovers a magical heirloom that allows him to step into the lives of his customers by wearing their shoes.

The film’s unique and quirky premise received mostly negative reviews from critics. It was seen as a strange mix of fantasy, comedy, and drama that didn’t quite work. It was one of several smaller, more unusual projects Sandler took on during this period of his career.

‘Pixels’ (2015)

Sandler starred in the science-fiction action-comedy ‘Pixels’. The film’s premise is that aliens misinterpret video feeds of classic 1980s arcade games as a declaration of war. They attack Earth using the games as models for their assaults. Sandler plays a former arcade champion who is recruited by the government to lead a team of old-school gamers to fight them.

The movie was a big-budget summer blockbuster that blended comedy with large-scale special effects. While it received negative reviews from critics, ‘Pixels’ was a commercial success internationally. The film’s nostalgia for classic video games was a major selling point for audiences.

‘Hotel Transylvania 2’ (2015)

Sandler returned to voice Dracula in ‘Hotel Transylvania 2’. In this sequel, Dracula is worried that his half-human, half-vampire grandson, Dennis, isn’t showing any signs of being a vampire. He enlists his monster friends to help him put the boy through a “monster-in-training” boot camp while his daughter Mavis is away.

The sequel was even more successful than the first film, breaking box office records upon its release. Sandler’s funny and heartwarming performance as the concerned “Vampa” (vampire grandpa) was again praised. The film’s success cemented the ‘Hotel Transylvania’ franchise as a global animation powerhouse.

‘The Ridiculous 6’ (2015)

‘The Ridiculous 6’ was the first film in Adam Sandler’s multi-picture deal with Netflix. It is a Western comedy that he co-wrote and starred in. He played Tommy “White Knife” Stockburn, an outlaw who was raised by Native Americans. He discovers that he has five half-brothers, and they all team up to rescue their estranged, bank-robbing father.

The film was heavily criticized upon its release, both for its quality and for its controversial humor. Despite the terrible reviews, Netflix reported that it was the most-watched movie on the streaming service in its first 30 days. This proved that Sandler’s audience would follow him from theaters to streaming platforms.

‘The Do-Over’ (2016)

The second film in Sandler’s Netflix deal was the action-comedy ‘The Do-Over’, co-starring David Spade. Sandler played Max Kessler, an FBI agent who fakes his and his old friend’s deaths to give them a chance at a new, more exciting life. However, they soon discover that the identities they’ve stolen belong to men in much deeper trouble than they ever were.

‘The Do-Over’ was an R-rated comedy that featured more action and intrigue than many of his previous films. Like the Netflix movie before it, it was not well-received by critics. However, it continued to draw a large number of viewers on the streaming platform, confirming the success of Sandler’s partnership with Netflix.

‘Sandy Wexler’ (2017)

In ‘Sandy Wexler’, another Netflix film, Sandler played the title character. Sandy is a talent manager working in Los Angeles in the 1990s. He is dedicated to his clients, a group of eccentric entertainers on the fringes of show business. His life changes when he discovers a genuinely talented singer at an amusement park.

The film is a more character-driven comedy, with Sandler portraying a funny and oddly endearing character with a distinct voice and mannerisms. The movie is a tribute to the entertainment industry and features numerous cameos from celebrities. It was seen as a more heartfelt effort than his previous Netflix films.

‘The Meyerowitz Stories (New and Selected)’ (2017)

Sandler starred in Noah Baumbach’s critically acclaimed film ‘The Meyerowitz Stories’. He played Danny Meyerowitz, one of three adult siblings who gather in New York to deal with their difficult, aging artist father, played by Dustin Hoffman. The film explores their complicated family dynamics with both humor and pathos.

His performance was met with universal praise, with many critics calling it the best of his career. He received a standing ovation at a prestigious international film festival for his portrayal of the sensitive and overlooked son. The role once again proved his incredible talent as a dramatic actor when working with top-tier directors.

‘The Week Of’ (2018)

Sandler co-starred with Chris Rock in the Netflix comedy ‘The Week Of’. They play two fathers from completely different economic backgrounds who are forced to spend the week together leading up to their children’s wedding. Sandler’s character, a working-class father, insists on paying for the entire wedding, leading to a series of chaotic and funny disasters.

The film is a more grounded, character-based comedy compared to some of his other Netflix projects. The story focuses on family and the love a father has for his daughter. The chemistry between Sandler and Rock, two longtime friends and ‘SNL’ alumni, was the main highlight of the movie.

‘Hotel Transylvania 3: Summer Vacation’ (2018)

In the third installment of the ‘Hotel Transylvania’ franchise, Sandler once again voiced Dracula. This time, Mavis surprises her father with a family vacation on a luxury monster cruise ship. Drac and the rest of the monster pack enjoy all the fun the cruise has to offer, but the dream vacation turns into a nightmare when Drac falls for the ship’s mysterious captain.

The film was another massive box office success, continuing the franchise’s global popularity. The story took the beloved characters out of the hotel and into a new, colorful setting. Sandler’s vocal performance as the lovestruck Dracula remained a key ingredient to the series’ charm and humor.

‘Murder Mystery’ (2019)

Sandler reunited with Jennifer Aniston for the Netflix action-comedy ‘Murder Mystery’. They play Nick and Audrey Spitz, a New York couple who finally go on a long-promised European vacation. A chance encounter leads to them being framed for the murder of an elderly billionaire, forcing them to go on the run and solve the crime themselves.

‘Murder Mystery’ was a massive hit for Netflix, breaking viewing records for the platform upon its release. The combination of comedy, action, and mystery, along with the proven chemistry of its two leads, made it incredibly popular with audiences around the world. It successfully launched a new film franchise for Sandler.

‘Uncut Gems’ (2019)

Sandler delivered another universally acclaimed dramatic performance in ‘Uncut Gems’, directed by the Safdie brothers. He played Howard Ratner, a charismatic and gambling-addicted New York City jeweler. The film is a tense, high-anxiety thriller that follows Howard as he makes a series of high-stakes bets that could lead to the windfall of a lifetime or his complete ruin.

His performance was electrifying and widely praised as a career-best. He won a major independent film award for Best Male Lead and received numerous other accolades from critics’ associations. Many felt he was unfairly overlooked for other major industry awards. The role showcased a frantic, desperate energy unlike anything he had done before.

‘Hubie Halloween’ (2020)

In ‘Hubie Halloween’, Sandler played Hubie Dubois, a good-hearted but eccentric community volunteer who is ridiculed by everyone in his hometown of Salem, Massachusetts. Despite the mockery, Hubie is dedicated to monitoring the town’s annual Halloween celebration. When people start to disappear, it’s up to the easily-scared Hubie to save the day.

This Netflix film was a return to the silly, character-driven comedies of Sandler’s early career. It was filled with his usual collaborators and had a fun, nostalgic Halloween theme. The movie was dedicated to the memory of actor Cameron Boyce and was a big streaming hit for Netflix.

‘Hustle’ (2022)

Sandler starred in the sports drama ‘Hustle’ for Netflix. He played Stanley Sugerman, a down-on-his-luck basketball scout for the Philadelphia 76ers. While abroad, he discovers a once-in-a-lifetime player with a rocky past. Against his team’s wishes, Stanley brings the phenom to the United States, hoping to prove they both have what it takes to make it in the NBA.

The film received widespread critical acclaim, with particular praise for Sandler’s heartfelt and grounded performance. His genuine love for basketball was evident throughout the movie. ‘Hustle’ was celebrated as a top-tier sports film and one of the best projects to come from his Netflix partnership.

‘Murder Mystery 2’ (2023)

Sandler and Jennifer Aniston returned as Nick and Audrey Spitz in ‘Murder Mystery 2’. Now full-time private detectives, they find themselves at the center of another international incident when their friend, the Maharaja, is kidnapped at his own lavish wedding. Their investigation takes them from a private island to the heart of Paris.

The sequel was another huge success for Netflix, proving the popularity of the characters and the franchise. It upped the action and scale from the first film, delivering another entertaining blend of comedy and suspense. The easy chemistry between Sandler and Aniston continued to be the film’s strongest asset.

‘You Are So Not Invited to My Bat Mitzvah’ (2023)

In this Netflix teen comedy, Adam Sandler took a supporting role, while his own daughters, Sunny and Sadie Sandler, took the lead. The story is about two best friends whose bat mitzvah plans are thrown into chaos by a popular boy. Sandler played Danny Friedman, the father of the main character, trying to navigate the drama.

The film received surprisingly strong reviews, becoming one of the best-reviewed movies of his entire career according to collected critic scores. Critics praised it as a charming and authentic coming-of-age story. Sandler’s warm performance as a loving, goofy dad was a highlight, and the film was celebrated as a true family project.

‘Leo’ (2023)

Sandler voiced the main character in the animated musical comedy ‘Leo’. He played a 74-year-old lizard who has been the class pet in a Florida elementary school for decades. When he learns he only has one year left to live, he plans to escape to experience the outside world, but he gets caught up in the problems of the anxious students.

‘Leo’ was a massive hit for Netflix, becoming the platform’s biggest animated film debut. The movie was praised for its humor, heart, and catchy songs. Sandler’s performance as the grumpy but wise old lizard was funny and touching, making the film a hit with both kids and adults.

‘Spaceman’ (2024)

In the science-fiction drama ‘Spaceman’, Sandler played Jakub Procházka, a Czech astronaut on a solitary mission to the edge of the solar system. Six months into his journey, he realizes his marriage back on Earth might not be waiting for him. He is helped by a mysterious, spider-like creature from the beginning of time that he finds hiding in his ship.

This was a contemplative and visually unique film that showcased a more introspective and somber side of Sandler’s acting. His performance as the lonely astronaut was subtle and melancholic. The film was a bold and artistic choice, further demonstrating his desire to work on diverse and unconventional projects.

‘Happy Gilmore 2’ (2025)

Adam Sandler reprises one of his most iconic roles in ‘Happy Gilmore 2’. The film sees Happy returning to the world of professional golf, this time competing on the senior tour. He must once again face off against his old rival, Shooter McGavin, while also dealing with a new generation of golfers and the challenges of getting older.

The sequel brings back the beloved characters and slapstick humor that made the original a 90s classic. Sandler easily steps back into the role of the hot-tempered golfer with a heart of gold. The film is a nostalgic treat for longtime fans and a massive hit, proving the enduring appeal of the character.

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