Highway Robbery, a collaboration between Freeway and Bay Area legend the Jacka, has been held up for years by logistical and legal hurdles—which is a shame, because it's the best and most natural-sounding project Freeway has been involved with since 2007. "Got with Jacka 'cause he pray like I pray," he growls on the album's second track, "Dunya", a reference to their shared Muslim faith. But the two share a lot more than that: they are both pained, repentant, and thoughtful, their lyrics glowing with hard-won wisdom and regrets. They are stubby, stocky, unlovely guys with devoted regional fans, and on Highway Robbery they sound like they've been sitting on the same porch together for decades.

The producers on Highway Robbery include the Jacka's frequent collaborator Jeffro and other Bay Area rap staples, like Traxamillion and Young L; the bulk of the music is low-key, liquid, and unmistakably bluesy. The guests that float through are on the same wavelength—Trae tha Truth on "Just Remain", Freddie Gibbs on "Cherry Pie". On "Write My Wrongs" Cormega drops by, whose stern and reflective new album Mega Philosophy put some metaphysical weight and writerly bite behind conscious-rap scolding. These are serious rappers, and you don't bob your head to Highway Robbery so much as nod slowly, your eyes squinted from the glare of all the old-head wisdom unfurling in front of you.

Highway Robbery isn't all hard-won old-man jewels, though. There are airy party tracks, too: "Sunnah Boys", featuring Killer Mike, high-steps through some jazzy keyboard chords and candy-coated synths. "Shuckin & Jivin" is a lip-licker sex jam from Young L, and it knocks like retooled "Mr. Me Too" stripped for scrap. It also represents one of two appearances on the album of wild card Husalah, a human exclamation point who lends unstable energy to any song he's on. Even though Highway Robbery is an independent release, Free and Jacka have somehow managed to liberate a Daft Punk sample, and a high-profile one, for "One More Time", and they slow it down and pump it full of low end.

Freeway raps in a lower register than normal, and he sounds incredible; more importantly, he sounds palpably at home. As a member of the scattered early-'00s Roc-A-Fella dynasty, he has a lot of past to compete with, and he's been working gamely against the cultural tide for the last few years, trying to reinvent himself as a backpack rapper and then as a nostalgia act. But here, he finds a milieu that suits him. He and Jacka trade lines with gusto and fire: "Pray you keep my family safe/ They didn't ask to be here, they shouldn't pay for my mistakes". The Jacka moans on "Dunya", "No matter how much I smoke, the pain won't burn away." "My close homies turned on me for no reason, they're such traitors," Free seethes, adding a gut-kicker: "My last album was only in fourteen stores."

Simply put, Freeway always works best when he's got a foil, and the Jacka is his most natural partner since Beanie Sigel slipped sadly off the grid. When you listen to him here you aren't, for the first time in years, pondering Roc-A-Fella. He's talked in interviews about being energized by the grind of artists like Jacka, who has built up a formidable mystique as a sort of Bay Area philosopher king, and frankly, Free should do three projects like this a year: the regional rap landscape is dotted with serious-minded, knotty rappers—Vic Spencer or Lil Durk from Chicago, or Young Moe from Alexandria, with whom he's worked before—who would make perfect complements. Free's hunger is a precious resource, and it's hard not to want to hear more of it in the world.