No Reason To Pretend is a weekly column by Stephen Kearse that explores the intersection of hip-hop and pop culture.
Issa, the main character of HBO’s Insecure, spends a fair share of her time in front of mirrors, rapping. Her raps, always self-written, are bad. The words fumble out, inflected at odd points, and connected by clumsy, simple rhymes. This roughness is intentional — Issa tends to turn toward rapping when she’s particularly emotional or facing hard decisions — and actor/writer Issa Rae, a veteran practitioner of awkwardness, sells it well. She truly cannot rap, and it’s funny to see her repeatedly try. But it’s not just a joke. The motif’s real treat is the explosive confidence that rapping always manages to create, however briefly. In a show about deeply ingrained insecurity, rap is a continual source of fleeting but thorough conviction.
Issa Rae has a well-documented history with rap. J, the protagonist of Rae’s breakout web series The Adventures Of Awkward Black Girl, also loved to rhyme. The show frequently played this up, giving her a rap song as a ringtone, jump-cutting to uncomfortable freestyles, and dedicating entire scenes to J enthusiastically reciting ratchet romps in the privacy of her car. The show’s soundtrack was just as driven by rap, featuring interludes backed by Ice Cube, Wiz Khalifa, Childish Gambino, 50 Cent and others. The Doublemint Twins, a joke group that Rae is actually a member of, also have a few choice features on the show. Outside of ABG, Rae once ran a vlog series titled Ratchetpiece Theatre, where she snarkily dissected various rap songs.