Issa Rae, ‘Rap Sh!t’ Cast Predict Grammy Winners, from SZA to Meryl Streep to Nicki Minaj

For Issa Rae, music has always been an extra cast member on the call sheet.

The nine-time Emmy nominee has used music as a storytelling tool, extending the voices of her complex and comedic characters — from the groundbreaking series Insecure and to her current adventure Rap Sh!t to the web series that launched her career, The Misadventures of Awkward Black Girl.

“Music elevates the storytelling of everything. I write to music, [and] you can have a scene that plays out great but music will add that little bit of tension, or that spark, or that feeling. It will cement a scene in your brain,” she tells The Hollywood Reporter. “There are so many songs that I associate with specific scenes that have also, in turn, affected my life and my memories, and it just adds an extra feeling to that song. So, they really work hand-in-hand beautifully.”

Rae is so connected to music that it’s hard to not think of her when you look at the nominees at the 2024 Grammy Awards. SZA is the top contender with nine nominations, and season 2 of Insecure was dedicated to the singer, playing the majority of her acclaimed debut album Ctrl; SZA even recorded an original song (“Quicksand”) for the series. Victoria Monét, who has seven nominations, helped close out season 3 with her track “The Glow” and also had a second song on the show’s soundtrack. Leon Thomas, who is nominated for best R&B song for SZA’s “Snooze,” played the role of Eddie aka “Neighbor Bae” on the show. And others who have been featured on Insecure or Rap Sh!t are nominated at the Feb. 4 awards show, including 6lack, SiR, Alex Isley and ThankGod4Cody, who is signed to Rae’s record label Raedio.

So it’s only appropriate that THR recruited Rae — along with the stars of Rap Sh!t (KaMillion, Aida Osman) — to predict who will walk away as winners at the Grammy Awards. In an interview, as they discuss their love for nominees like SZA, Nicki Minaj, Janelle Monáe and Meryl Streep, the breakthrough actresses also dote over their bad-ass boss while Rae — who stars in the box office hit Barbie — breaks down her dance to Dua Lipa’s “Dance the Night” in the film.

Issa, what’s it like to see artists who were featured on your shows competing at the Grammys?

It’s an honor that Insecure has been able to feature so many artists, given them their first syncs. We’ve done the same on Rap Sh!t, and to see them be awarded and acknowledged at the Grammys, I feel proud of them, and I feel proud of our collective taste in our ears. We’re obviously fans first — that’s why they make it onto the soundtracks. So, we’ll continue to be fans and root for them forever.

Let’s get into these predictions, starting with ALBUM OF THE YEAR, which is dominated by female acts. The nominees are: SZA, SOS; Taylor Swift, Midnights; Olivia Rodrigo, Guts; Miley Cyrus, Endless Summer Vacation; Jon Batiste, World Music Radio; Lana Del Rey, Did You Know That There’s a Tunnel Under Ocean Blvd; Janelle Monáe, The Age of Pleasure; boygenius, the record.

AIDA OSMAN I think Taylor Swift, only because of the pattern of the Grammys [and] who they love. But I want SZA to win.

ISSA RAE I think SZA’s gonna take it. Taylor Swift didn’t even cross my mind, which means I’m not the demographic. I haven’t heard it. I’ve heard it’s great, and people are comparing her to Michael Jackson. I don’t know which people are doing that — whites! But I’m gonna give it to SZA.

KAMILLION I love Lana Del Rey. I’m like, “Where you been girl?” But I think I’ma give it to SZA for sure.

RAE Janelle Monáe’s album was phenomenal.

OSMAN: Yes it was.

RAE Yeah, come on. Show us some more titties. Ha ha.

KAMILLION Titties! We needed you.

Do y’all have a favorite song on SZA’s album?

RAE “SOS.” It just started off right. It just transports you into a world. Oh, and “Blind.”

OSMAN I like “SOS” because it’s like her take on Frank Ocean a little bit, but she’s like yelling it. It’s so cool. “All that sauce you gave for free!”

RAE I like that actually.

Year after year we see the rapper or the R&B artist of the year lose, while Taylor could win her fourth album of the year Grammy. I mean, Beyoncé has lost how many times? 

RAE That was infuriating.

So a lot of us are wondering if SZA could actually win. How devastating would it be if she doesn’t win?

KAMILLION I don’t think it will be disappointing. I think she knows that she’s that girl and what she deserves. Sometimes you just don’t get what you deserve, and eventually you do. But I’m rooting for her. I think to see the girl that we relate to … win a Grammy? Like, that’s big. But she’s ain’t going to stop if she don’t win.

OSMAN She’s got nine nominations. I think she’d be really proud of that. We love SZA. And Taylor has Ice Spice on that album, too. That “Karma” track. So, it’s like, she tapped us. She tapped us.

RECORD OF THE YEAR: SZA, “Kill Bill”; Taylor Swift, “Anti-Hero”; Billie Eilish, “What Was I Made For?”; Miley Cyrus, “Flowers”; Victoria Monét, “On My Mama”; Olivia Rodrigo, “Vampire”; Jon Batiste, “Worship”; boygenius; “Not Strong Enough.”

OSMAN I think TikTok won. All of these songs are TikTok songs. I can not avoid these on the internet.

KAMILLION I want Victoria Monét to win, but I think Miley Cyrus is going to take this. Or Billie. (Looking at Issa), “Did you hear that song a lot? It was in Barbie.”

RAE I didn’t hear that as much as I heard Dua Lipa [“Dance the Night”] and “I’m bad like the Barbie” [Nicki Minaj and Ice Spice’s “Barbie World”]. But I like “What Was I Made For?” The first time I saw Barbie and I heard that song, I got chills. I was like, “This is beautiful.”

There’s Olivia Rodrigo. Is she killing it?

OSMAN The kids love her. They will die about that girl. She’s a Disney girl.

RAE I honestly think Taylor Swift will take record of the year. And if she takes record of the year and SZA gets album of the year, then everybody’s happy.

That’s true because Taylor has never won record of the year, so I think she’d be very happy.

RAE Let’s only give her that.

BEST NEW ARTIST: Ice Spice; Victoria Monét; Jelly Roll; Coco Jones; Noah Kahan; Gracie Abrams; Fred again; The War and Treaty. 

And I want to point out that The War and Treaty is a country-soul married duo, and the female member (Tanya Trotter) was in Sister Act 2 and sang “His Eyes on a Sparrow” with Lauryn Hill.

RAE Oh shit! Yo, it pissed me off in Sister Act 2 when she got interrupted, because that stupid nosy nun came in. They were getting it in, and I never got to … Well, I guess it’s on the soundtrack. But, anyway, I will be looking them up.

KAMILLION I’m just confused at Jelly Roll and Victoria Monét — they’ve been killing it for a minute. Like it’s underdog season, but how they get [nominated for] best new artist?

OSMAN I don’t know Jelly Roll.

KAMILLION I know Jelly Roll. Gang gang.

OSMAN The country artist? Are you friends with Jelly Roll?

KAMILLION Gang gang.

OSMAN OK! Gang gang with Jelly Roll.

RAE Wow. You’re so versatile.

KAMILLION Jelly been killing for a minute. I remember when he was in the clubs. Jelly tapped in.

RAE Where’s he from?

KAMILLION He’s from the country-country. He a country boy. Tatted up, piercings. He rockin’ with us.

OSMAN Maybe Jelly Roll’s going to win best new artist. Probably.

KAMILLION I think so. I think Jelly Roll’s gonna win.

RAE I feel like Ice Spice will probably take it ‘cause her come-up is crazy. And the Grammys, they’re always like, “We’re cool!” And I feel like they’re going to want to acknowledge her rapid ascent and give it to her, because she’s been able to do a lot in a short time. But I love Coco and I love me some Vicky Monét.

BEST R&B SONG: Halle Bailey, “Angel”; SZA, “Snooze”; Victoria Monét, “On My Mama”; Coco Jones, “ICU”; Robert Glasper, SiR and Alex Isley, “Back to Love.”

OSMAN Oh no, this is hard!

RAE This is very hard. I mean, these songs are great. And because it’s R&B, the Grammys are like, “This is for the Blacks.” So anybody can take it.

OSMAN I think “On My Mama” will win. It had such a big year. “Snooze” was amazing, too.

RAE I’m torn between “On My Mama” and “Snooze.”

KAMILLION “ICU” did really good. I like “On My Mama” but I feel like it hasn’t been out long enough. As far as “Snooze,” I just hear that song all the time, everywhere. So either “ICU” or “Snooze.” But I would like to see Victoria take home something.

OSMAN I heard “Snooze” at Walgreens the other day.

KAMILLION But shout-out to Halle though. I feel like she should be in the pop category. Where are the Black girls in pop?

RAE Was “Angel” a pop song?

KAMILLION It’s poppy.

OSMAN It’s poppy but she was singing.

KAMILLION It’s like pop-R&B.

OSMAN Need a new category: P&B.

KAMILLION Create the category like you did best African music performance. Let’s go!

KaMillion, you have written for so many artists including Rihanna, H.E.R., Trey Songz and Keke Palmer. If you could write a song about Issa and Aida, what would it be about?

KAMILLION It would be the greatest song on Earth. I think it would sound like a box of crayons. I don’t know if crayons have a sound, but it would sound like a box of crayons. It would smell like Baccarat. And it just would be shaking ass all over the world. Even in New Zealand.

Issa and Aida, y’all approve?

OSMAN I love it!

RAE Yeah. I love coloring.

KAMILLION It will be very fun. It will be comical, ‘cause they’re funny as hell. Very witty.

RAE Takes one to know one.

KAMILLION Thank you girl.

BEST R&B ALBUM: Victoria Monét, Jaguar II; Babyface, Girls Night Out; Summer Walker, Clear 2: Soft Life EP; Coco Jones, What I Didn’t Tell You [Deluxe]; Emily King, Special Occasion.

KAMILLION I didn’t know Babyface had an album out. But shout-out to the legend.

OSMAN I just seen him at a restaurant. I’m going with Victoria Monét’s Jaguar II.

RAE: That or Summer Walker.

This is Summer’s first nomination for her own music. She was previously nominated for appearing on Kendrick Lamar’s Mr. Morale & The Big Steppers but had never earned a nomination for her own songs or albums.

KAMILLION For real? All those albums. Seriously?

RAE Then they’re not gonna pick her.

OSMAN How is Soft Life EP [in an] album Music News? I’m confused.

An EP can be in an album category.

OSMAN There’s no rules anymore.

RAE Yeah, they just be making shit up. I think Coco Jones’ album was very, very good. But I don’t know that they’re going to give it to her. Well, maybe they will. I don’t know.

KAMILLION I’m stumped on this one.

RAE I’m stumped.

OSMAN I always pick who has the most nominations. Victoria — she has seven.

BEST TRADITIONAL R&B PERFORMANCE: SZA, “Love Language”; Babyface and Coco Jones, “Simple”; PJ Morton and Susan Carol, “Good Morning”; Kenyon Dixon, “Lucky”; Victoria Monét, Earth, Wind & Fire and Hazel Monét, “Hollywood.” 

Victoria’s 2-year-old daughter is nominated here and could make Grammy history if she wins.

OSMAN Aw. So cute. They need to put Hazel in movies. She’s so cute.

RAE She’s adorable.

OSMAN Put her in Boss Baby, like live action. Give her a film. Issa, let’s write a film for Hazel.

RAE I’ll do that tomorrow.

KAMILLION “Love Language” maybe.

RAE How does “Love Language” go again?

(Interviewer sings SZA’s “Love Language”)

RAE You’re not giving me nothing. I could have done that (laughs). SZA has like 43 tracks [on that album].

OSMAN Victoria Monét and her baby. Her baby girl.

KAMILLION Let’s do it Victoria.

RAE And Earth, Wind & Fire. You can’t beat them. They’re legacy R&B, if you’re talking traditional.

BEST MELODIC RAP PERFORMANCE: Doja Cat, “Attention”; Lil Durk and J. Cole, “All My Life”; Drake and 21 Savage, “Spin Bout U”; SZA, “Low”; Burna Boy and 21 Savage, “Sittin’ on Top of the World.”

RAE How does “Low” go?

OSMAN (Singing) “I’m the lowest of the low…”

RAE Oh! I love that song! (Starts singing “Low” with Aida). I still don’t know what “Love Language” is.

I think Burna Boy and 21 Savage because they [sampled] Brandy. It’s a recognizable song. Everybody knows it, you know, from 20 years ago, 30 years ago? 

KAMILLION How does “Attention” go?

OSMAN Is it the, “Bitch I said what I said…”

KAMILLION That’s not it. That’s not that one. I woulda known that one. That’s my girl. “I’d rather be famous instead, I let all that get to my head.” That’s not that one. “Ooh, she a rebel, she a…”

That’s “Paint the Town Red.” That’s nominated in the pop category. She’s rapping more on “Attention.”

RAE: She must be melodically rapping (laughs).

KAMILLION I think Lil Durk and J. Cole. “They been tryin’ to keep me down.”

OSMAN I think “Spin Bout You.” I don’t have an opinion here. I think it’s my favorite song out of all of them. It’s not an educated guess, it’s just what I want.

BEST RAP SONG: Nicki Minaj and Ice Spice, “Barbie World”; Doja Cat, “Attention”; Lil Uzi Vert, “Just Wanna Rock”; Drake and 21 Savage, “Rich Flex”; Killer Mike, André 3000, Future and Eryn Allen Kane, “Scientists & Engineers.”

RAE I don’t think I’ve heard “Scientists & Engineers.” That’s embarrassing for me. I love me some Andre 3000.

KAMILLION I mean, he is playing flutes now.

RAE Yeah, which I love.

OSMAN And them overalls. Shout-out to them overalls. Give a Grammy to them overalls.

RAE Give a Grammy to that face! Mm-hmm.

KAMILLION I think Lil Uzi Vert…

RAE I can’t contest that.

KAMILLION Nicki Minaj and Ice Spice might take it for the [win].

OSMAN That movie did a billion dollars…

RAE I think they’re going to [win] for the soundtrack Music News. 

The crazy thing is Nicki Minaj has never won a Grammy.

RAE She’s never won a Grammy?

OSMAN Really?

RAE Has Lil Kim ever won a Grammy?

Yes, but only for “Lady Marmalade” with Christina Aguilera, Pink and Mya.

OSMAN (Rolling eyes) Oh, wow.

RAE They are disrespectful. But they disrespect rap a lot. Well, I think Nicki’s going to take it on one of these. “Barbie World” was too big.

KAMILLION “Super Bass” didn’t win? That’s crazy. Wow.

BEST AFRICAN MUSIC PERFORMANCE: Burna Boy, “City Boys”; Tyla, “Water”; Davido and Musa Keys, “Unavailable”; Ayra Starr, “Rush”; ASAKE and Olamide, “Amapiano.” 

KAMILLION All these songs is big. This is going to be a tough category for them to choose from.

RAE Yes, they’re superstars.

KAMILLION Like “Amapiano,” I was just turning up to that yesterday. “City Boys” is crazy. Ayra Starr, “Water,” I don’t know man. I can just tell you who I want to do a song with — Burna Boy.

OSMAN She’s an opportunist. I’m going to say Tyla’s “Water.” Just because I couldn’t escape the song. I also can’t do the dance at all. I’ve tried so much.

KAMILLION I’m going to say Davido or Burna Boy.

OSMAN I don’t know a lot of these songs, which is embarrassing as an African.

RAE I, too, think they’re going to give it to Tyla because they are as ignorant as me.

KAMILLION Because it’s more popular, right?

RAE Yeah, it’s TikTok-y. And Trevor Jackson remade it, so obviously that’s going to take it [to the top]. (Laughs).

BEST AUDIO BOOK, NARRATION, AND STORYTELLING RECORDING: Meryl Streep, Big Tree; Michelle Obama, The Light We Carry: Overcoming In Uncertain Times; Senator Bernie Sanders, It’s OK to Be Angry About Capitalism; William Shatner, Boldly Go: Reflections on a Life of Awe and Wonder; Rick Rubin, The Creative Act: A Way of Being. 

Michelle’s Becoming won this award in 2020 and Viola Davis’ win last year made her an EGOT. Meryl still needs a Grammy and Tony to become an EGOT.

RAE That’s a cheat code.

Michelle already won, so I can put my Rooting for Everybody Black aside. Give it to Meryl, because she deserves the EGOT. I’m sorry. Give it to her. I feel like they, the Grammys, know they want to give it to her. They want her to be acknowledged for her greatness.

OSMAN Also, if there is a white actress that would be Black…

RAE Because they say that she kind of looks like Future, too, so there it is.

OSMAN No way!

RAE They have similar features. Have you seen the Future and Meryl Streep side-by-side? 

OSMAN I’m actually just noticing.

KAMILLION I want Meryl Streep to win.

RAE That is so pure. There was just no explanation. “I want her to win.”

OSMAN I think Rick Rubin is going to win. I can’t escape this creative act on TikTok. It’s everywhere. “Ideas are living things. Ideas are…” It’s beautiful advice. I’m just saying it’s everywhere.

BEST SONG WRITTEN FOR VISUAL MEDIA: Nicki Minaj and Ice Spice, “Barbie World”; Billie Eilish, “What Was I Made For?”; Dua Lipa, “Dance the Night”; Ryan Gosling, “I’m Just Ken”; Rihanna, “Lift Me Up.” 

Issa, what was it like doing the dance to Dua Lipa’s song in Barbie?

RAE Dancing to it was my worst nightmare. It was the worst day of my life. It was the best day of my life being on that set. It was exciting, and then literally the first day, I had to learn the choreography to shoot the [following] day. And it was terrible. We also didn’t have the lyrics to the song. Greta was like, “Oh, it’s going to be a Dua Lipa song.” But all we had was the instrumental, so I was just like, “What the fuck is this? What am I dancing to? (laughs).” And for that, I want “Barbie World” to win because I didn’t have to dance to that.

KAMILLION I want my boss’ movie to win.

OSMAN I’m kind of stuck. I guess we’re both kind of stuck. Rihanna has been our boss in another way, too, so I don’t want to cause friction.

RAE But “Lift Me Up” was very sad.

OSMAN And it wasn’t an album. It still wasn’t a Rihanna album.

RAE It wasn’t the album. Everybody was expecting a single.

KAMILLION She won’t give us one. She won’t give us one.

RAE And I feel like … nevermind. Not going to complete that thought.

OSMAN I’m going to say “What Was I Made For?” by Billie Eilish.

RAE What do you want to win?

KAMILLION Barbie.

OSMAN I want “Barbie World” to win because I love Ice Spice and Nicki Minaj.

KAMILLION (Looking to Issa) And we love you.

KaMillion and Aida, what has it been like working for Issa? How is she as a boss?

KAMILLION She’s been such a joy. She’s so inspiring. It’s so crazy watching her work. Sometimes you think she has a twin because she’s everywhere. She’s like Santa Claus. How can you be everywhere and [giving] all these gifts? She’s always on time, no matter what. And it’s like, “How are you on Rap Sh!t set every day and you had all this shit dropping and I ain’t even know about it, and then you just drop stuff on your timeline like it ain’t nothing?” I’m like, “What? You did that, too?” So yeah, I want to be like her. She’s a fucking mogul, man. I mean, coffee shops!

RAE Thank you. I feel like she said it for everybody.

OSMAN You don’t want me to tell you how much I love you? What can I say? I love you so much. I’ve loved you for years. You’ve been on my screen way more than you could imagine. I used to play Insecure when I was in college because there were not a lot of Black girls in my school. I went to school in Nebraska, and I wanted to just hang out with my girls, so I would just let Issa and Molly sometimes play on mute while I wrote. I want to be just like her.

RAE Thanks so much for that.

KAMILLION And it’s not just because you’re sitting right here. We really feel like that.

OSMAN Yeah. It’s not because you pay me a lot.

KAMILLION Yeah. You pay real well.

RAE Yes, thank you. She pays well (laughs).