One Nightstand With Issa Rae

In One Nightstand, celebrity readers and writers join us at The Blond in 11 Howard to discuss some of their favorite books, allowing us to learn about their tastes and lives in the process.

Issa Rae has a confession. “I don’t think L.A. is a good dating city,” she says, shrugging. “I for sure romanticized it in Insecure, knowingly. I was like, ‘I’m deceiving people. I don’t care. This is what I want it to be.’”

The 40-year-old actor and writer may be out of the dating trenches — she married her husband, Louis Diame, in 2021 — but the slippage between the world she wishes existed and the one that does continues to be where she makes magic in her work. Her new essay collection, I Should Be Smarter by Now, is an honest account of the challenges that come with rising in Hollywood, from receiving tough feedback to learning to dish it out.

“It’s hard to work in a creative industry and collaborate with other people if you can’t be completely honest with them,” she says of her work. “As a creative myself, I know what it’s like to get my feelings hurt when I feel like I’m delivering what I think is the best parts of myself and my creative work and you don’t like it. So, I’m really sensitive in how I deliver news that I don’t appreciate something, or I don’t understand something. I’ve learned over time how to navigate that, but it’s a constant dance.”

In the essay Playing Well With Others, she writes about collaborating with director Melina Matsoukas while making Insecure. “That was the best example of working with her in a way of like ‘Oh, we’re on the same team,’” says Rae. “There were also other moments where I was like, ‘We will fight. We’re going to come to blows. But I respect you so much and I respect your opinion, and I respect the way that you think.’ And that should happen. I should be able to be like ‘I want to beat your *ss right now and you want to beat mine, and we’re still going to work together and it’s going to be fruitful.’”

Learning how better to navigate life’s challenges is a common through line in the books that Rae finds herself drawn to. She read her first recommendation, The Courage to Be Disliked by Fumitake Koga and Ichiro Kishimi, in January. “The most I read is generally in January, and I thought it was a great new year’s resolution book,” she says. “If you’re in a period of your life where you are determined to just shed and change, then this is for you.

“This book is really good because it almost frees you of the burden of your past defining you, which I find really powerful,” she adds. “It’s obviously easier said than done, but just the notion that that’s possible I think can help someone to at least try to overcome whatever it is they're going through.”

Her second book, The Wilderness by Angela Flournoy, tells the story of five friends over a 20-year friendship. “I actually met Angela in my 20s when I was in New York, as she was friends with one of my roommates,” says Rae. “We only knew each other in the club, brunch, dinner scene, and so I didn’t know the extent of her talent.”

Rae’s been a longtime fan of Flournoy, adding that she was “blown away” by the author’s 2015 debut, The Turner House. “She’s been through so much, and the way she writes people, you feel like you know them.”

An exec Rae works with recommended her third selection, Great Black Hope by Rob Franklin.“I love ensemble stories, but this was just so fresh and from a perspective that I was familiar with,” Rae says. “It just felt like it was asking questions that we don’t often ask about Black privilege, and also art and class in a way that was really, really compelling to me. And it was just juicy. It was a coming-of-age story that felt unique, but also something that I might see in an elevated CW show, which I love.”

Her final book, Eleanor Oliphant Is Completely Fine by Gail Honeyman, was attractive to her because of the humor, which Rae also keeps close to the surface in her work. “There was her clearly being on the spectrum in some way and the way that she was so blunt about things in an almost Amelia Bedelia-esque way,” says Rae. “It made me laugh so many times. Unexpectedly.” She adds: “And I found myself crying at parts in the book and I wasn’t expecting that. I really felt I wanted her to be happy.”

Watch the full interview below.