After five years, Issa Rae’s beloved Web series turned HBO hit “Insecure” is entering its fifth and final season on Sunday. The series’s web of complex, endearing and often messy relationships has been the regular subject of Twitter discourse, recap podcasts and group chats since its premiere in 2015. The show has been lauded for being real, funny and having an incredible soundtrack.
Ahead of the premiere, we asked series regular Natasha Rothwell to make us a playlist inspired by the show. Rothwell plays Kelli, one of Issa’s college friends, and is known for bringing levity, life and plenty of zingers to every scene she’s in. But Rothwell isn’t just the show’s life of the party; she’s also a supervising producer who has written and story edited more than a dozen episodes of the show. Remember the poignant season four finale when Issa and Lawrence finally reunite years after their breakup, parsing through years of their relationship in a tender, dreamy and sometimes painful bottle episode? Rothwell wrote that one, and she’s not done yet. This past April, she signed a multiyear deal with ABC Signature, where she’ll be developing upcoming television projects.
The romantic-comedy buff curated a list of 10 songs to make you feel like you’re living in a rom-com, “Insecure” style.
Listen and read along with her commentary, edited lightly for clarity, below.
I can’t resist an ’80s throwback bop. I also can’t help but dance when I hear this song. It’s a vibe.
I love covers because I get to experience the familiar in a new way. This cover of Stevie Wonder’s “Overjoyed” is truly beautiful. I mean, it just hits different.
If you ever see me driving in L.A. and I’m singing my heart out, I probably have a crush and I’m most likely singing this song and doing my best to harmonize with Mega.
Music is a huge part of my writing process. I almost always make a playlist for the projects I’m working on. The right song can set the tone and even inspire. I wrote a rom-com over quarantine. When it sees the light of day, see if you can spot the “Snoh Aalegra” moments.
I’m a Libra, which means I’m always crushing on somebody. So, when I first heard this song, I had no choice but to go crush-hunting. Anyway, if you get a random flirty text from me next summer, this song is why.
I grew up in the church, and I love it when a secular song about romantic love gets the gospel treatment. And let me tell you, this song understood the assignment.
This year, cuffing season started the moment this song was released.
It’s no secret that I absolutely love karaoke. So, a word of advice for the newbies who want to tackle this song: Be careful. Any song brave enough to start with the chorus might inspire you to try and hit notes not meant for you. And yes, I am speaking from experience.
I’m glad this song didn’t come out when I was in high school. I almost certainly would have tried to enlist the school band to accompany me during a sportsball half-time big romantic gesture. I wish I were kidding.
If saying this gets me canceled, so be it: “Hold the Line” is Toto’s best song, not “Africa.” Now, you can either fight me on this or just play it the next time you’re getting ready for a date and thank me. Choose wisely.