Issa Rae’s office in South Los Angeles overflows with trinkets from her many successes. Awards perch on virtually every surface. Three boxes of President Barbie dolls, her character from last year’s biggest blockbuster, sit high on a shelf. There are purple roses, bottles of LeBron James’ Lobos 1707 tequila—a company Rae invests in—and custom pillows from Insecure, her hit HBO series that ran for five zeitgeist-capturing seasons. But at the moment, the item that Rae is most excited about is her brand-new Moleskine notebook. Rae buys a new notebook every year and fills it with personal reflections, creative ideas, and tasks to complete for her many businesses. Last fall, her 2023 journal started getting so full, she wrote in smaller and smaller fonts to preserve space.
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“Now these conglomerate leaders are also making the decisions about Hollywood. Y’all aren’t creative people. Stick to the money,” she says. “The people that are taking chances are on platforms like TikTok: that’s what’s getting the eyeballs of the youth. So you’re killing your own industry.” “I have my little stake in this limited plot of land, and I’m gonna make sure that I bring in as many people to live on it as possible,” she says. “So until we run out of opportunities, they’ll be good.”
