insecure issa rae hbo

Issa Rae Talks Music, Storytelling, and HBO’s Insecure

If there’s one word every millennial can relate to, it’s “insecure.” From navigating the complications of friendships and romance to making it in the career world, there’s nothing like adulting to give you an existential crisis. This feeling is captured perfectly in Insecure, a smart, relatable, and very original comedy series you need to be watching.

Insecure follows Issa and Molly, best friends and black women who are not exactly “killing it.” Over the course of the season, the two women have to face their own real-life flaws as they attempt to navigate different worlds and cope with an endless series of uncomfortable everyday experiences. Think everything from karaoke fails ending up on YouTube to relationship drama to code switching.

Created by, written by, and starring Golden Globes nominee Issa Rae, the series received rave reviews when it debuted on HBO last October. In celebration of this month’s release of the first season on digital download – just in time for us to work through all of our insecurities in the New Year – Fangirlish had the opportunity to chat with Issa about music, storytelling, and all things Insecure.

insecure issa rae

LOS ANGELES, CA – JANUARY 10: Actress Issa Rae speaks to reporters during HBO’s Insecure Takeover at West Hollywood’s The Den on sunset in celebration of digital download release on January 10, 2017 in Los Angeles, California. (Photo by FilmMagic/FilmMagic for HBO)

The past year has been quite the journey for Rae, who prior to the release of Insecure, was best known for her YouTube series The Misadventures of Awkward Black Girl. But just days after attending the Golden Globes (she received her first nomination for Best Actress in a Comedy Series for Insecure), Issa couldn’t be more humble. “I was so glad to experience [the Globes], but I’m so glad they’re over,” she said. “It hit me that week – a week back from break, basically, and I was like, Holy shit, this is like, a worldwide thing. People are gonna be watching. My family started hyping it up, like, Oh my god, Issa, you’re gonna be on TV! and What’s the dress? I was like, I don’t know the answers to any of these questions! But being there, I was surrounded by all the people I love and [my] heroes. I’m glad I was even able to be a part of it in some way.”

Though Issa may share some insecurities with her character when it comes to stressful situations, the success of the show’s first season has strengthened her confidence in other areas. “I think the show has made me feel more confident in my storytelling and being able to tell other stories – feeling like I can tell stories that people can relate to and work in a collaborative environment and put my ego aside,” she said. “This is the story that I wanted to tell, but a lot of it is acknowledging that so many people are making this story so much better than I could have imagined. I love that aspect of it.”

Of course, coming off of a strong freshman season presents its own pressures and challenges as Issa looks toward Season 2. “There’s a combination of comfort, but also stress,” she said. “Because the response was so positive to the first season, I don’t want to necessarily feel like I have to top that, but I want to match it in some way without feeling like I’m compromising the creativity. There’s an added level of pressure, and I’m trying not to think about it.”

“Because the response was so positive to the first season, I don’t want to necessarily feel like I have to top that, but I want to match it in some way without feeling like I’m compromising the creativity.”

Some of that pressure comes from the audience, who of course have their own opinions about Issa and Molly (and their jobs and love lives). Though Issa misses “creating within a vacuum,” as she did with Season 1, she’s committed to keeping the story real. “You want to tell a relatable story, but you can’t help but to be influenced by the outside world. That is the biggest challenge, taking that into account – trying to shut out everybody else and just be like, What is the story we’re trying to tell? and to make sure that it’s still a good story at the end of the day,” she said.

insecure issa rae hbo

From the “Bish Please” to “Insecuri-Tea,” INSECURE-themed cocktails were a hit at the show’s Season 1 digital release event in West Hollywood. (Photo by Fangirlish)

Whatever direction the story takes in Season 2, we know one thing: there’s sure to be an amazing soundtrack to back it up. The soundtrack for Season 1 is available now, and it’s definitely worth a listen. Issa talked us through how it came together: “I knew just from a personal standpoint, I was like, If I ever have a show, the music has to be on-point. I don’t care how garbage my show is – the music is gonna be great,” she said, laughing. “Having [Executive Producer] Prentice [Penny], who had a deep love for hip hop, and [Executive Producer] Melina [Matsoukas], who comes from the music video world… She brought on Solange, who is a DJ and of course is a musician herself and has amazingly eclectic taste. All of that combined. We were really passionate about making sure the music of the show told a story too and reflected the characters properly.”

The soundtrack features a strong selection of music from both indie and established artists that touch on a variety of social and relationship issues highlighted in the series. And of course, it wouldn’t be complete without Issa Rae’s hysterical “Broken Pussy,” featuring Kelis. As for Issa’s personal favorite tracks? “I love GoldLink’s ‘Palm Trees,’ I love Guordan Banks’ ‘Keep You In Mind’… That’s something I brought to the table. I was like, If there’s a sex scene, I know what I want to have sex to! I know what I want to cheat on my man with! This song.

So besides putting together another must-see season of Insecure, what’s next for Issa Rae? “I want to do so much more,” she said. “I want to work with other artists and other storytellers. I want to continue to produce, I want to go into film, I want to go into unscripted – any media that I can – and highlight women and minority voices. I love the challenge of telling stories.”

We’ll be here to watch and listen to them.

Insecure: Season 1 is available now on digital download. The official soundtrackMusic From The HBO Original Series Insecure, is also available now from all digital music providers.

Interview has been lightly edited for clarity. 

Fangirl, avid reader, & Anglophile. Current obsessions include: Dylan O'Brien, Teen Wolf, Game of Thrones, brunch, SDCC, and gingerbread lattes. Not a queen, a Khaleesi. Contact: