Grade: 3.0/5.0

Kaseem Bentley had three major goals with his move to the Bay Area. One, to record his new stand-up comedy album Lakeview at a live show in San Francisco. Two, to visit his mother. And three, to see how his beloved hometown of San Francisco is “turning to shit.”

Bentley, a former teacher, grew up in the Oceanview neighborhood of San Francisco. Known by locals as Lakeview, the steadily gentrifying neighborhood has been described as “hard to find.” And it’s just one of the neighborhoods in San Francisco that has undergone tremendous change in the past decade. Bentley jokes in his album about the new sort of locals he’s observing — and it’s everyone from tech whizzes working at start-ups to activists dedicated to the cause of saving “lesbian seagulls.”

Lakeview is an album that finds its strengths in Bay Area-centric humor. Nestled within well-received crowd work, in which Bentley takes great pride in raking his audience over the coals, the references to the absurdity of fighting for a seat on BART as well as to Bentley’s observations about how Latinx culture has changed over the years generate the most appreciative laughter from his audience. But if tapping into locals’ sentimentality toward their town is where the album is at its most beloved, it’s in Bentley’s hard-hitting race-based quips that the album is at its most ambitious.

Bentley, after all, is pulling no punches and is sparing no one. Lakeview opens on Bentley joking with an Indian audience member who had called Bentley out for making a blanket statement about how homogeneously white the crowd was.

“I don’t know what it is about Indian people selling out Black people,” Bentley quips, before moving on to his next target, a white audience member who looks “like a Jonas brother who didn’t get famous.”

Whether or not someone appreciates race-related jokes is a matter of taste, but it’s a risky territory that Bentley navigates strategically, shifting between critical, thoughtfully crafted monologues and ridiculous one-liners. His reflections on race are woven into his familiarity with the Bay Area — and that’s why so much of it lands.

Despite success with this subject matter, Bentley tilts in the latter half of the album toward a completely different array of topics. At 41, Bentley has finally begun to reflect on getting older and on building his legacy. For Bentley, getting old is like being stuck between a rock and a hard place — or rather, between taking Metamucil and having to attend a party when you’d rather be eating frozen yogurt. Although the segment is as relatable as the rest of the set, it doesn’t earn as many laughs.

Bentley’s’ energy — so exuberant at the album’s start — dips somewhere along the way. By the time listeners arrive at the penultimate track on the album, “Ugly Couples with Ugly Babies,” they may feel a longing to return to the album’s stronger opening. The lull could have been softened had Bentley committed to stronger vocal choices when impersonating the characters of his stories.

In particular, there’s one character Bentley stands to speak more of: Keisha, the hypothetical daughter the comedian dreams of adopting one day. Bentley endeavours to capture Keisha’s essence in the final, nearly eight-minute segment of the album, building his original momentum. It’s here that Bentley wears his heart on his sleeve; the affection and joy with which he describes children like Keisha is so palpably personal, especially when Bentley draws upon anecdotes from his time working as a teacher.

In some ways, Bentley’s work as a teacher has continued. Lakeview is abundantly truthful, reflective and thoughtful. What becomes clearest is that Bentley is a man who knows himself well and refuses to sugarcoat his experiences. And it’s here that the fourth intention for his return to the Bay Area emerges — Bentley is here to impart his wisdom, and we’d do well to listen to what he has to say.