Award-winning actor and comedian Adam Sandler has captivated comedy lovers for nearly four decades. Fans fell in love with him as a cast member on “Saturday Night Live,” where he debuted onscreen in 1991. After being fired from “SNL” in 1995, the Brooklyn, New York, native began creating now-classic comedy films like “Billy Madison,” “The Wedding Singer” and “Happy Gilmore.”

The five-time Primetime Emmy nominee solidified his place in Hollywood with performances in films like “Punch-Drunk Love” and “50 First Dates,” alongside Drew Barrymore. He poked fun at the woes of fatherhood in his 2010 film “Grown Ups” and brought humor to Hanukkah in the animated comedy musical “Eight Crazy Nights.”

But Sandler began his career as a stand-up comedian and has had several successful sold-out comedy tours. His latest, “You’re My Best Friend,” is currently underway. Here’s a look at our five favorite, and slightly underrated, moments from his career.

A prison football saga in ‘The Longest Yard’ with Nelly

A remake of the 1974 comedy, “The Longest Yard,” was a fun sports flick featuring familiar faces and fellow funny guys Chris Rock, Tracy Morgan and Terry Crews. Sandler portrays washed-up football player Paul Crewe, who’s found himself in hot water after being accused of shaving points during games. Persistent bad behavior lands Crewe a three-year prison sentence, where he helps lead a team of inmates against the guards in a football game.

“The Longest Yard” received mixed reviews following its release. But fans loved the sports banter and comedy. Plus, it was also the major motion picture debut for St. Louis rapper Nelly, who starred as the all-star running back for the inmates’ team in the 2005 film.

An endearing performance in ‘Spanglish’

Although it wasn’t one of his most popular films, “Spanglish” is a feel-good dramedy that showcases Sandler’s acting range. The 2004 film — directed by 22-time Emmy Award winner James L. Brooks — is about John Clasky (played by Sandler), a father and husband balancing family growing pains with the weight of career success. In the midst of discovering his wife is having an affair, Sandler begins falling in love with his housekeeper, a Mexican immigrant played by Paz Vega.

In the end, Sandler’s character doesn’t leave his wife for the housekeeper. She’s still learning to speak English while caring for her young daughter, who doesn’t understand why their life is so different from the rich American family she works for.

Sandler’s performance in “Spanglish” was endearing and bold. The film is full of unspoken truths about life — the differences that tear people apart and the similarities that bond them together, no matter what language they speak.

A humorous Hanukkah in ‘Eight Crazy Nights’

Sandler brought an animated comedic edge to Hanukkah when the film “Eight Crazy Nights” was released in 2002. The movie didn’t do so great at the box office, raking in nearly $10 million less than what took to create, but for Sandler fans, the outrageous humor in “Eight Crazy Nights” keeps it a favorite.

He’s joined by characters voiced by his wife, Jackie Sandler, and Rob Schneider as they navigate Sandler’s wild approach to holiday cheer.

Seriously in debt in ‘Uncut Gems’

The 2019 crime-thriller “Uncut Gems” depicted Sandler in a light completely different from what fans had experienced in his past work. He traded humor for a serious role, bringing to life Howard Ratner, a gambling addict who can’t seem to keep his deals or pockets straight.

The movie features an all-star cast, with Sandler starring alongside LaKeith Stanfield, Julia Fox and former NBA player Kevin Garnett. While the ending isn’t triumphant like in many of his comedies, some critics raved that it was one of Sandler’s best roles, a sincere performance rooted in the highs and lows of addiction.

A new generation of fans with ‘Happy Gilmore 2’

The sequel to his 1996 fan-favorite comedy “Happy Gilmore,” Netflix’s “Happy Gilmore 2” created a new generation of Sandler fans when it debuted in July. It had been nearly 30 years since viewers had seen Happy Gilmore on the golf course. And although he started a bit rusty, by the films end, the memorable character was hitting his signature soaring shots.

Like many of Sandler’s movies, “Happy Gilmore 2” included an endless number of celebrity cameos. Ben Stiller and Julia Bowen returned to their roles from the original. Billboard chart-topper and future Super Bowl halftime performer Bad Bunny played Gilmore’s golf caddie, plus Kansas City Chiefs player Travis Kelce, Post Malone, Kid Cudi and more all made appearances. Sandler even slipped in a clip of the late Cameron Boyce, the young actor who starred as his son in “Grown Ups.” It was a heart-tugging tribute to Boyce, who died in 2019.

“Happy Gilmore 2” was a stellar comedy experience that reminded viewers how good it feels to laugh freely.

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