In recent years, Chattanooga has emerged as a sort of musical sister city to St. Augustine. Local punks caravan up to this scenic slice of Tennessee for weekend mini-fests once or twice a year, while DIY River City acts like Rowdy Downstairs and Sal Atticum have recorded music in Oldest City mainstay Jacob Hamilton’s home studio.

That may not seem to have much to do with rising rapper Isaiah Rashad. But the ’Nooga native’s second album, 2016’s The Sun’s Tirade, is a simmering stew of hypnotic grooves and staggering lyrical insight. Like the First Coast itself, Rashad knows how to stretch his legs, exuding a playful, Southern-fried beauty while possessing far deeper roots than what first meets the eye. It takes multiple listens to fully appreciate Rashad’s far-reaching range, just like it takes a long time to truly understand the intricate, often paradoxical layers of Northeast Florida. And, hey — Rashad recently described The Sun’s Tirade to XXL as “a long, hot-ass day … [Like] a conversation with the sun.” If there’s one thing we Floridians know, it’s long, hot-ass days spent conversing with (and cursing) the sun.

Rashad got his first big break by signing to modern rap superstar Kendrick Lamar’s Top Dawg Entertainment label. And, like Lamar, Rashad knows how to flex his muscle over nearly any strain of hip-hop — thundering trap, brassy boom-bap, avant-garde soul, luxuriant G-Funk. But the outer sheen of The Sun’s Tirade, which greatly improves upon Rashad’s already promising 2014 debut Cilvia Demo, masks a far starker core, with Rashad vocally and openly addressing the pitfalls of depression, drug addiction, isolation in response to success, procrastination and, most of all, parenthood.

The year-and-a-half that Rashad spent working on The Sun’s Tirade coincided with the first year-and-a-half of his first son’s life; in August, his family expanded with the birth of another child. “For a majority of [that time], I was coming to a realization about what I really wanted this to be about,” Rashad told XXL last September. “I realized I could’ve talked about anything, [but] I tried that general ‘have fun’ shit and threw those out because they didn’t mean anything to me. And then I was like, ‘How can I convey how I feel in a way that won’t sound like I’m depressed?’”

It’s ultimately up to the listener to decide whether The Sun’s Tirade hits that mark, but to this listener’s ears, the album sounds nuanced, painstaking and meditative. Rashad kicks “Rope // rosegold” off with the line, “When I’m sober / I might testify”; on “Dressed Like Rappers,” he sheepishly says, “I can’t admit / I’ve been depressed / I hit the wall / Ouch.” But on “Stuck in the Mud,” he sounds more hopeful: “Can I sleep for a while? Can I work on myself?”

Given the rap game’s long tradition of boisterously delivered bullshit, those clear-eyed one-liners are staggering (and sound even better on record). But Rashad’s true skills are highlighted on the invigorating “Free Lunch,” which weaves a three-minute bildungsroman that plumbs the psychological depths of making it as a successful rapper by reminiscing about the first numbers Rashad memorized as a kid: the last four digits of his Social Security number, which he had to recite every day at school to get his free lunch.

That sense of unfiltered humanity kept Rashad afloat in the years between Cilvia Demo and The Sun’s Tirade, when he became addicted to a potent mixture of Xanax and alcohol, fought regularly with his closest confidants, and was almost kicked off the Top Dawg Entertainment label. And that’s the last thing anyone expected from the scene-stealing rookie who wowed crowds as an opener for Juicy J, Joey Bada$$ and ScHoolboy Q and earned praise for his live TV performance at the 2013 BET Hip-Hop Awards with Kendrick Lamar.

“After Cilvia Demo, the highs of how tight that was, when I came back down to Earth, it was like, ‘Damn, I did do a whole bunch of shit that was fucked up that I have to deal with’,” Rashad told XXL last fall. “[I was] having a hard time being a rapper for real — balancing responsibilities, maintaining friendships with people I work with, people I came up and moved across the country with — and taking the responsibilities of being an artist [and] a dad [seriously].” When Rashad started falling out with those longtime friends, TDE CEO Anthony “Top Dawg” Tiffith sent him back home to his mother in Chattanooga, who delivered her son back to LA two weeks later with a fresh haircut and a fresh perspective on his career.

“My mom always says 25 is when you get some type of common sense,” Rashad told XXL shortly after his birthday last May. “Some type of awareness of what you’re supposed to do. You can figure out your way through the bullshit a little better. Stuff starts making sense and you start making plans.” Which means Rashad’s Lil Sunny Tour stop at Jack Rabbits this week presents a rare chance to get up close and intimate with the artist Pitchfork recently called “one of rap’s most promising talents” — and that rare MC who values substance, honesty and introspection over flash, pretensions and braggadocio.

“I’m really a recluse,” he told XXL. “I don’t talk about shit. So [with The Sun’s Tirade], I was like, ‘I could make something up,’ but I figured telling the truth would be easier than lying.”