The comedian reveled in the discomfort of taping the Josh Safdie-directed ‘Love You.’

There’s a moment in Adam Sandler’s new comedy special, Love You, when the comedian picks up an acoustic guitar and very intently and fluently plays “Malagueña,” the classical guitar instrumental by Cuban composer Ernesto Lecuona, before he launches into “Mutterin’,” a comedic song about murmuring negative asides under his breath.

In Sandler’s first Netflix special in six years, he finds humor in most things — whether it be a low-brow, scatological sketch about a wish-granting genie, or a clever riff on non-sensical word pronunciations as he toggles between spoken bits and songs. But one thing Sandler takes very seriously is his musicianship.

“When I was a kid, my dad had an acoustic guitar, and he would play ‘Malagueña.’ That song means a lot to me,” Sandler tells Billboard.  One day, Sandler — who was already taking guitar lessons while growing up in Manchester, New Hampshire — came upon a Stratocaster in a store window. “I was in bands all through junior high and high school and I said, ‘Oh my God, I would do anything for that guitar.’ My dad said, ‘I’m not just going to get it for you, but if you learn “Malagueña” note for note, I’ll get that guitar for you.’ I practiced it for a year until my father was impressed enough he got it for me when I was 12. I think of that every time I pick up a guitar.”

And he picks up the guitar a lot in Love You, which was directed by Josh Safdie, whom Sandler worked with to great acclaim on the 2019 drama Uncut Gems. Instead of the usual comedy special where the comedian walks out onto a brightly lit stage to applause, Love You opens with a decidedly more frantic, in-your-face tone.  Sandler pulls up to the venue dealing with a shattered windshield, he’s then barraged by autograph seekers, he can’t find a clean hoodie to wear, his coffee order is wrong, and he’s running late. Once he gets on stage in the darkly lit small club — a deliberately disheveled Nocturne Theater in Glendale, California — things aren’t much better: there are technical glitches with the screens, and a stray dog even wanders onto the stage.

When Safdie came to him with his slightly skewed vision for the special, Sandler says, “It definitely took me a little while to go ‘yes.’ I just thought we were going to shoot the show because I had been doing the show for a while and I had that down, so I was excited to do that, but Josh kept saying, ‘Let’s try to do something different.’” The special is a scaled-down version of the arena show Sandler took on the road last fall, which grossed $28.5 million in 27 shows, according to Billboard Boxscore.

Though Sandler knew some of the curveballs that were going to come his way at the Nocturne, Safdie’s plan kept Sandler on his toes, and gives the special a jagged edge. “That made it more exciting the days we were shooting,” Sandler says. “I definitely never knew when something was going to come at me and throw the rhythm off, and I had to try to react and keep the show going as smoothly as we could. It made it more of an electric vibe.”

As if there wasn’t enough disruption, an unplanned kerfuffle breaks out between some audience members. “It was kind of early on in the show, and then all of a sudden you felt some hostility in the crowd,” says Sandler, who quickly diffused the situation. “When you’re on the road, it’s going to happen. Things get out of control in the audience and you got to react to it and try to calm things down.”

Just as his 2018 special, 100% Fresh, ended with a sentimental, sweet musical tribute to the late Chris Farley, his friend and former Saturday Night Live castmate, Love You similarly concludes with “Here Comes the Comedy,” a warm salute to the healing power of comedy, as footage of the dozens of comedians who have influenced and delighted Sandler since his youth appear on the finally operational monitors. In the six-minute number, written by Sandler and his longtime musical partner Dan Bulla, Sandler plays the Stratocaster his father gave him when he was 12.

Sandler apologizes that he has to cut the interview short because he’s in the middle of pre-production on Happy Gilmore 2, his sequel to his 1996 comedy classic. The movie will start shooting in New Jersey next year and Sandler’s already teased that the new version will include a number of cameos, just as the original did, including Kansas City Chiefs tight end Travis Kelce, who sported a Happy Gilmore cap at this April’s Coachella. “He’s gonna come by. He’s a very nice guy,” Sandler said on The Tonight Show on Aug. 20.  “You guys would love him in real life. What a big, handsome guy. Funny and cool as hell. He’s a stud and he’s so funny.”

There’s no word on whether Kelce’s girlfriend, superstar Taylor Swift, will also make a cameo, but Sandler is an unabashed Swiftie. He and his family attended a Los Angeles show on the Eras tour in August 2023, as well as the Los Angeles premiere of Taylor Swift: The Eras Tour concert film. When asked his favorite Swift song, Sandler struggles to pick just one, but it’s clear he has plenty riffling through his head from years of being the ultimate girl dad.

“Everything [my two daughters] throw on I love, but one of the first ones they threw on when they were young was ‘The Best Day,’” he says of Swift’s sentimental track about her mom from 2008’s Fearless. “We connected with that when the kids were young. Every album, we listen the first day it comes out. There’s not a song they don’t know every word to.”

Like Swift, Sandler is no stranger to the Billboard charts. Between tunes like “The Chanukah Song,” The Wedding Singer’s “Grow Old with You” and “The Thanksgiving Song,” as well as his Grammy-nominated comedy albums, Sandler’s landed on 10 different charts, including topping the Comedy Albums chart in 2019 with his 100% Fresh album. It’s something he’s kept an eye on since his early days.

“When I was young and my albums came out, I worked with Brooks Arthur,” he says, referencing the renowned late music producer whom he collaborated with for nearly 30 years. “He  used to talk to me about his charts and I’d ask him, ‘How are we doing on Billboard?’ I always wanted to know.”