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Television Review

In HBO's ‘Insecure,’ Issa Rae is winning even when she’s losing

Issa Rae stars in “Insecure,” a new HBO show based on her Web series “The Misadventures of Awkward Black Girl.”John P. Fleenor/HBO

I encounter it all the time, as a gay man. Someone is looking for a stylish shirt, or the toniest restaurant, and he or she will turn to ask me, openly assuming I’ll know. Because all urban gay men are up on chic culture, all gay men know where to shop and how to cook, all gay men are fabulously fashion-forward. To me, it’s not an insult, necessarily, so much as a misguided assumption based on media-bred stereotypes.

I am not a Bravo gay, as anyone who knows me, my wardrobe, and my favorite restaurants can confirm.

And Issa is not the black woman many of the people around her, black or white, expect. In her smart, charming new HBO comedy, “Insecure,” Issa Rae portrays a woman — also named Issa — who works with a group of white people at an LA nonprofit that enriches education for black kids. With what they feel is respect, Issa’s colleagues treat her as the big expert in all things black or black-ish. “They think I’m the token with all the answers,” Issa says in a voice-over, when one eagerly asks her the meaning of “on fleek.” She doesn’t like it, being boxed in, presumed upon, unknown behind the stereotypes, but she smiles — with tinges of passive-aggression on her lips — through it all.

At another point in the “Insecure” premiere, which airs Sunday at 10:30 p.m., Issa is addressing a group of grammar school students. A black girl asks her, “Why you talk like a white girl?,” a comment that gets big laughs from the other kids while it makes Issa squirm.


But “Insecure” expands beyond Issa’s racial identity; it’s a lovely comedy about identity in general — romantic, professional, and sexual, as well as racial — and how to forge your own despite other people’s preferences. Developed by Rae and Larry Wilmore, based on Rae’s Web series “The Misadventures of Awkward Black Girl,” “Insecure” keeps these broad notions of self-realization alive in the background of the series, as a valuable context.


And then in the foreground, they give us the extremely specific and winning Issa, who is turning 29 in the premiere. Issa is dissatisfied with her life as she approaches 30, not just her patronizing workplace but her live-in boyfriend, Lawrence (Jay Ellis), who’s passive in all aspects of his life, including Issa. She wants to blossom, but she is, as the title has it, insecure. She doesn’t find making changes an easy process — who does? — which is why she delivers rapped, improvised affirmations to herself in the mirror on a regular basis.

Issa is far from a sad sack, in case I’m making her seem that way. She’s full of energy and good humor, which emerges repeatedly, including a freestyle rap at a nightclub about her friend’s broken body part — and romantic life — that had me laughing out loud. A montage in which Issa tries on different colors of lipstick — and the personalities that go with them — also cracked me up. She is an easy TV character to root for, with her bright and yet irony-tinged spirit. She is particularly funny with her best friend, Molly, a corporate attorney played with sharp wit by Yvonne Orji. Molly is more assertive than Issa, as she tries to find a boyfriend online, but she’s dealing with her own loneliness. Together, they’re too much fun to watch, with enough chemistry between them to create a fresh TV spin on the female buddy relationship.


And what actually happens on “Insecure”? Not an awful lot, which is a virtue. Like “Louie,” “Atlanta,” and “Better Things,” the show operates more as a slice of life than as a plotted story. It’s an extraordinary portrait of an ordinary, relatable, and delightful person.


Starring Issa Rae, Yvonne Orji, Jay Ellis, Lisa Joyce. On HBO, Sunday at 10:30 p.m.

Matthew Gilbert can be reached at gilbert@globe.com. Follow him on Twitter @MatthewGilbert.