Judd Apatow digs deep with his comedies, exploring the pain beneath the punchlines. After working on the now-cult-hit coming-of-age sitcoms Freaks and Geeks and Undeclared, Apatow carved out a filmography that traces the major milestones of adult life: sexual awakening (The 40-Year-Old Virgin); pregnancy (Knocked Up); illness (Funny People); reaching middle age (This is 40); and committing to relationships (Trainwreck).

Apatow’s latest film, The King of Staten Island, is his most poignant yet. A story of loss and mental illness, it confidently punctuates drama with comedy rather than the other way around. And it hums with a raw, messy energy that captures the mood of the moment.

The opening scene is unlike anything in Apatow’s previous films. Scott Carlin — a semi-fictional version of star Pete Davidson — barrels down the highway in a distressed state. He closes his eyes, unconcerned about the risk he’s taking. This moment recalls Davidson’s cryptic, seemingly suicidal Instagram post from just two years ago.

The film goes on to paint an alternative portrait of Davidson’s life that depicts what might’ve happened if he didn’t pursue comedy and land a spot on Saturday Night Live. In this alternate universe, he’s an aspiring tattoo artist still living with his mom (Marisa Tomei) and reeling from the loss of his father to a fire. (Davidson’s real father was a firefighter who died on 9/11.)

When Scott’s younger sister (Maude Apatow, Judd’s eldest daughter) goes off to college, he’s left to help their mother cope with empty nest syndrome while wrestling his own demons. He mostly tries to drown them with drugs.

Scott’s mother throws a wrench in the works when she falls into a whirlwind romance with Ray (Bill Burr), a Staten Island fireman. Scott initially tries to sabotage the relationship but ends up befriending Ray and peeking inside his father’s life by hanging around the firehouse. This is where the film stops meandering and really finds its footing.

In one of his early interactions with the firefighters, Scott bemoans the idea of them having families, spewing bitterness about his father leaving his behind in the line of duty. Later on, the senior of the squad, Papa (Steve Buscemi), says his piece about why heroes deserve families. Scott nods and comes to empathize, shamelessly shedding a grudge he’s held onto for years. It’s refreshing to see this kind of civil discourse during a time in which so many people refuse to swallow their pride and open their eyes to non-toxic perspectives. As Papa speaks from a good heart and Scott lets his guard down to truly listen, you’ll think, “Why is this so fucking hard for others right now?”

This scene’s warm, tender dialogue also stands out given the fact that it’s delivered by Buscemi, who fought fires in the ’80s and returned to his engine company after 9/11 to help sift through the rubble of the World Trade Center.

The film’s strength lies in its authenticity. Its world feels lived-in and achingly real. The performances have a naturalistic quality as well. When Scott finally confesses his love for his longtime casual girlfriend, Kelsey (Bel Powley), it’s far from a cinematic gesture. He doesn’t spit out a perfect monologue or deliver his few lines in the most romantic way possible. He awkwardly, bluntly blurts out his thoughts as most people would.

Burr delivers the best, most complex performance of his career. He makes you feel the weight of his character’s sloppy life and his desperate desire to pick up the pieces, even if that means bonding with someone who tried to wreck everything all over again.

As his mother and sister, respectively, Tomei and Apatow capture the bitterness beneath their concerns for Scott as well as the love that ultimately shines through their wounds.

Yes, the film is funny, too. But the laughs come as relief. They’re not the top priority here. Among many other things, that makes The King of Staten Island Apatow’s boldest film yet.

The King of Staten Island will be available on VOD starting Friday, June 12.