Jalen Rose cracks jokes with ‘scrappy’ comedian Yvonne Orji

Actress and comedian Yvonne Orji, known for playing Molly on the HBO hit “Insecure,” has an enviable Hollywood career. But she also has an incredibly unorthodox résumé for showbiz — one that exemplifies the old Sinatra tune “My Way.” On this week’s “Renaissance Man,” the Nigerian American talked me through her conversion from academia to comedy and how she landed a massive role with barely an acting credit to her name.

“I grew up in a very strict immigrant household,” she told me. “I didn’t even know entertainment was an option. I was focused on STEM, science, all of that stuff. And I got my master’s in public health before I even realized that entertainment was a possibility. I was ‘Bamboozled by Jesus,’” referring to the title of her 2021 memoir.

Raised outside of DC, she attended a fancy Pennsylvania boarding school so she could be around the elite. But while in school, she heard a calling into the arts world from two entities: Jesus Christ and organic chemistry.

“I definitely was still on track to being a doctor. And I think it was when organic chemistry told me, like, ‘Girl, you might want to pick another major.’ And I was like, ‘You right’ … That was the hard decision to say, ‘Hey, Mom and Dad, I’m not going to go to med school.’”

She realized she enjoyed reading books. And last I checked, the Bible is a book. She become born again. Yvonne also entered a beauty pageant, which required her to have a talent. After learning that getting straight As was not a sanctioned one, she prayed for divine invention. And no joke, she told me God said she should do comedy, which gives me hope that Richard Pryor is in heaven.

“So slowly I leaned into it and I had two weeks to prepare. People ended up laughing, and the rest is history.” She now has two degrees (undergrad and master’s) and an HBO comedy special. She has opened up for Chris Rock at MSG and is now also hosting the dating show “My Mom, Your Dad” on HBO Max. Romance is an interesting lane because Yvonne, 38, is vocal about saving herself for marriage and has noted the irony that her last name is pronounced “orgy” but she’s a virgin. You could say she’s self-aware and self-deprecating.

She’s also scrappy. Before she became an actress, she was hosting shows, weddings and funerals. One of those gigs landed her on the radar of “Insecure” co-creator and star Issa Rae.

“Issa actually saw me hosting a fashion show, and then she came out to see me do
comedy and was just like, ‘Yo, that was funny.’ But this is years before ‘Insecure.’ So we kind of had a black girl in LA trying to make it, you know, vibe about us, and so it was just like we respected each other.”

When casting began for “Insecure,” Yvonne was trying to crossover into acting, but she had no representation. She enlisted a friend who worked for a management company.
“Basically the arrangement was, if I make it on the show, I give them a cut … So it’s a lot of actors, actresses that have résumés out the wazoo, they’re killing it. And I’m just like, ‘Oh, OK, well, I’m just going to list in the fact that I am Yvonne Orji, and that is enough.’” She made an impression by talking with her hands and creators saw there was “something there.”

“I was not their first choice going into the auditions, but every time that I auditioned, I kept getting better because behind the scenes … I was choosing between paying my cellphone bill or getting a private tutor for an hour, and I was like, ‘Well, listen, they’re going to have to notify me by email if I get it, because my cellphone will be cut off. And so it was just all the little things I was doing to give myself a fighting chance. And so they noticed it and they were like, ‘Each time you came, you kept giving us something different. You kept adding to it, you kept becoming the character.’ And then [they said], ‘If she’s doing this without any direction, imagine what she could do when we give her, what we actually want for her to work with.’”

In sports terms, it’s like Jimmy Graham getting drafted in the NFL with only one year on the gridiron. But she attributes that work ethic to her immigrant background. Even when she was bullied as a kid, her mother told her: “I did not come to this country for you to make friends.”

She admits that was harsh, but it pushed her. She only saw herself succeeding — even if she was an underdog in places like Hollywood. And “Insecure,” which she helped make a huge success, had a cascade effect in the industry. “I think it changed the landscape of TV … for certain what is possible for black shows.”

What’s next for Yvonne? Well, med school is clearly off the table, though she can conquer anything at this point, and she would have a great bedside manner. Whatever it is, we know one thing: She’ll be led by that Jesus GPS. And I’ll be tuning in for it all.

Detroit native Jalen Rose is a member of the University of Michigan’s iconoclastic Fab Five, who shook up the college hoops world in the early ’90s. He played 13 seasons in the NBA, before transitioning into a media personality. Rose is currently an analyst for “NBA Countdown” and “Get Up,” and co-host of “Jalen & Jacoby.” He executive produced “The Fab Five” for ESPN’s “30 for 30” series, is the author of the best-selling book, “Got To Give the People What They Want,” a fashion tastemaker, and co-founded the Jalen Rose Leadership Academy, a public charter school in his hometown.