Jonah Hill is taking a smoke break when a building security guy who looks like he hasn’t taken an ounce of shit since the Nixon administration gives him an earful. “There’s no smoking within 15 feet of the front door,” the man scolds. Hill dutifully scurries a few storefronts down the Manhattan sidewalk, muttering some annoyance under his breath. Then, with the anxious excitement of a teenager, he spends a solid 10 minutes detailing the complications of being a Kanye West fan in the MAGA-hat era. “It’s starting to feel like we’re on the wrong side of history,” he concludes, voicing the concern of a generation brought up on Kanye’s blustering brand of ambition.

At 34, Hill is a comedy veteran, a two-time Oscar-nominated actor and, with this week’s coming-of-age gem Mid90s, a film director. He’s also an obsessive music nerd. This becomes clear throughout Mid90s, which stars a tight crew of foul-mouthed and gold-hearted skaters in Los Angeles during the time of Ninja Turtles and chain wallets. Within the film’s first few minutes, the 13-year-old main character sneaks into his older brother’s room and gawks in awe at a row of period-perfect rap CDs—albums by the likes of Mobb Deep and Gang Starr that were painstakingly chosen by Hill, who also wrote and music supervised Mid90s. From there, it feels like a minute doesn’t go by without a song breaking in. He takes every opportunity to spotlight his favorites, from Philip Glass to the Pixies, but the movie’s many moments that play out to ’90s rap are especially meaningful to Hill.

“Hip-hop is often butchered in film—it’s usually used to show someone driving through the hood or making a billion dollars and buying champagne—but it was the emotional backbone for me growing up,” he says in the offices of A24, the indie production company that’s backing Mid90s. “So a large ambition in making this film was to frame A Tribe Called Quest or Wu-Tang Clan in the same way that the Beatles were framed to our parents’ generation.”

He mostly listens to hip-hop in his everyday life, including the boom-bap sounds of his youth and newer artists like Drake, Earl Sweatshirt, and Fat Tony. But he is decidedly not into a lot of today’s most viral hip-hop. He even gave the adolescent stars of his film iPods filled with ’90s touchstones in hopes of turning them away from SoundCloud rap. And, according to Hill at least, it worked. “I’ve gotten them to admit that their generation’s music is trash,” he says with some pride.

And yet, as he talks about the songs streaming through his headphones as of late—from ’60s psych to ’70s singer-songwriter fare to classical—it seems that, by and large, his ear is still open.

Harry Nilsson is my favorite, he’s the OG to me. His voice is so beautiful, and I love his sense of humor, and the pain beneath it. We had his song “Without Her” in Mid90s at one point, in a scene where the kids in the film were listening to it in the car. But then we realized that the scene was way better with no music—and because it was me being corny, and obviously these kids aren’t listening to Harry Nilsson. A lot of times you pick songs you’ve always wanted to see in a film because they’re so great, and then you’re like, “OK, what’s appropriate for this story?”