ISSA RAE

Spreading the wealth

- Andrew R. Chow

ISSA RAE'S OFFICE IN SOUTH LOS ANGELES overflows with trinkets from her many successes: a Peabody award; pillows from her HBO show Insecure, which ran for five seasons; boxes of President Barbie dolls, her character from last year's biggest blockbuster. But at the moment, the item Rae is most excited about is her new Moleskine notebook. She buys one every year and fills it with personal reflections, creative ideas, and tasks to complete for her many businesses. "I love Mondays, and the first of the year is like a super Monday for me," she says. "To be able to open a new journal was very exciting in the nerdiest way possible."

Rae, 39, is especially determined to turn the page because last year was "not fun at all," she admits. In public, she was crushing it: she stole scenes in two of the year's most hyped films, Barbie and American Fiction, and released the second season of her critically acclaimed Max show Rap Sh!t.

But as the tagline for Season 3 of Insecure read, "glowing up ain't easy." And in her quest to become a media mogul on the level of Oprah or Debbie Allen, Rae has faced growing pains: she had to lay off eight employees during the WGA and SAG-AFTRA strikes, and watched projects get sidelined or canceled. In January, Rap Sh!t was axed by Warner Bros. Discovery. Perhaps worst of all, Rae says she's witnessed backsliding on pledges to increase representation and diversity. "I've never seen Hollywood this scared and clueless, and at the mercy of Wall Street," she says.