Rae Khalil Talks Def Jam Debut, Collaborating With Freddie Gibbs & What Anderson .Paak Taught Her

Releasing a debut album is understandably daunting, but releasing your first album on a major label is a much different ball game. Not many people can say that their major label debut LP follows a head-turning stint on a Netflix hip-hop reality competition show ( Rhythm + Flow ) and a Grammy win alongside Billboard Hot 100 -topping cross-genre savant Anderson .Paak . Then again, there’s only one Rae Khalil.

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Speaking with Billboard via Zoom just days before the release of Crybaby – a luscious 13-track R&B fantasia that finds her moving from low-key neo-soul to jaunty new jack swing – Rae Khalil is on the precipice of a life-changing career shift to complement the turbulent tides of her personal life. Across the four-year journey to Crybaby, grief has relentlessly reared its head; Khalil lost her grandmother this year and her great-aunt passed “a couple [of] weeks ago,” which significantly altered her approach to completing her new LP and sharing it with the world.

“I would say I’m now dedicating this project and this part of my life to her and my family,” Khalil muses. “I think the No. 1 [thing] is being intentional and accepting all the emotions as they come. Some days are stronger than others.”

As she awaits Crybaby’s arrival on DSPs, some of those days were spent watching House of the Dragon – which she namechecks as the last time she shed a few tears herself. Officially released on Aug. 9, Crybaby cements Khalil’s major-label metamorphosis by way of slick production contributions from a bevy of craftsmen, including .Paak and Nascent, as well as winning collaborations with the likes of Freddie Gibbs , Benny Sings, Khal!l, Tiana Major9 , Zacari, AA Rashid and .Paak himself.

Sure, the cast of characters has gotten exponentially larger, but Crybaby is perhaps Khalil’s most honest and arresting work yet. The anxiety that comes from weighing the sacrifice of aligning yourself with the label system against maintaining complete independence grounds the LP, giving the record a worthy thematic center to match its generally gritty grooves. “My compass does just fine on its own/  So much pride, it built a second home/ I can’t hide behind me no more,” she croons on the stunning lead single “Is It Worth It?”

With a deluxe edition in the works and her eyes on an upcoming tour, Rae Khalil is ready to fully step into and own her own spotlight with Crybaby. In an intimate conversation with Billboard , she opens up about her four-year recording process, what she’s learned from Anderson .Paak, and the unfortunate mishap that gave way to a collaboration with her favorite rapper.

A lot of people got to know you through Rhythm + Flow back in 2019. What lessons did you bring from that experience to the creation of Crybaby ?

I would definitely say trusting my guts. It’s five years ago now, [it was] such a great time period in my life. I remember taking advice from a lot of people at that time and listening to what other people thought I should be doing. I learned that this is my career, I’m the one [who’s] going to be standing on the brand of Rae Khalil. If there’s anything that I’m making or doing, I really want to stand behind that 100%.

Why did “Crybaby” feel like the appropriate title track for this album?

I thought it’d be a cool idea to change the narrative for what that means. “Crybaby” originally has a negative connotation, of someone who’s a whiner. I wanted to switch it to be someone who doesn’t have a problem with being vulnerable and sharing the parts of themselves that are maybe a little bit more on the sensitive side… not being worried about what others think. Kind of repurposing the word, making it more positive.

When was the last time you cried?

S–t, I’m telling you that episode [of House of the Dragon] was so good last night, I did shed a couple of tears! But in all seriousness, this has been a pretty tough year for my family. We lost a matriarch in our family in my grandmother, and a couple weeks ago, we lost her sister as well, so it’s kind of a generational shift happening, but it’s allowing me to be more present. I think it’s making me focus on the lessons and values that my grandma taught me my whole life and implementing that in my career and my personal life.

How has it been for you suffering these kinds of losses, but also rolling out this project which obviously marks a major moment in your career?

Life will always happen, and it’s up to us to figure out how we are going to endure and persevere. I do think that there’s some type of poetic thing happening with losing people [who] were in my life and shaped my ideology. That chapter of my life is now closed, and [there are] so many new opportunities, especially in my career. I have opportunities to travel and meet new people and get to know myself more. I look at it as a beautiful tapestry of good and bad. It’s what’s required to happen for more growth.

What were you listening to in the house growing up and what were you listening to during the sessions for Crybaby ?

When I work on albums, I’m just so in the music process that I’m not really listening to music. I love driving back from the studio with just silence, and then I’ll dabble with some of the new songs coming out, but it really takes me a second to get back into the groove of being an avid music listener of what’s new.

But what shapes any talented artist is the diversity in what you listen to, right? [Growing up], I had Motown and soul and R&B, but I also really enjoyed *NSYNC and Backstreet Boys. That was my era of pop music — Britney Spears, Christina Aguilera, Destiny’s Child. Then I would hear Anita Baker and The Jackson 5 on the weekends while we’re cleaning. And my brother would be listening to Evanescence and my aunt would be listening to David Bowie and then my grandma’s listening to f—king Jean Carne and Sarah Vaughan.

Talk to me about how “Come Home” came together. There are really strong New Jack Swing vibes on that one, which gives the tracklist a nice jolt of energy.

I made that song two weeks before I had to turn in the project. It was really just a magical moment. I had another song [in its place], but certain things about it wouldn’t get cleared in time. So, I was in panic mode and I was like, “Well we need something with high energy because [the album is] just going to be a very R&B thing if we don’t have some type of upbeat moment.”

I just recently met Khal!l through Instagram, and he sent me a collection of songs, and “Come Home” was one of them. I went to the studio the next day and I made that song in three hours. I love that song so much.

How did you get AA Rashid on the intro?

“Hot Track” is my favorite song, and Shid is a mentor of mine, a very good friend and spiritual adviser. He just loves me. Obviously, I listen to Griselda, I’m a big fan — but a friend of mine would talk to me about his lectures. Some of them are on YouTube, and I watched a couple and really gravitated towards some of the things that he talks about.

Randomly, I was just in downtown LA with my partner at a liquor store and he was in there, and I was just like, “Wait, Oh my God!” We started talking and he had a book on him that he wrote, and he told me to buy it and I did – that was years ago. Then we just became friends; I just met him on the street and that night we ended up going to his house and hanging out. He’s just the best and has always been in my corner and always been a fan of my music.

It really was just me asking, “Hey, I know you do this for Westside Gunn, is there any way you could just come and sit and talk?” So, we just recorded him talking for about 10 minutes, and it was really me and my engineer that pieced it all together. I like how it sounds like a sequence, but it really is not. We had to move things around, that’s what’s so fun.

“Hot Track” is such a powerful song. My longtime collaborator and producer Jared Rubens found that sample; that song was probably one of the first songs we made in our New York sessions for this album, which had to be December 2022. I’m sitting there and I’m listening and asking about the sample and he’s like, “I don’t know, some song [“When Morning Comes”] by O.C. Smith.” I got chills because I’ve been hearing that name my whole life; he was a longtime friend of my grandmother’s. They traveled to Africa together. He had a church that my grandma went to, and he married my mom and my dad.

Jared didn’t even know any of this! Out of all the songs he could have sampled, it’s this song by this guy who was very close to my family. It was so reaffirming and reassuring that this is exactly what I’m supposed to be doing. That song means so much to me, especially now that my grandmother has passed. She had the opportunity to hear the song, and she really loved it.

Who is Cisco and why did he get a song named after him?

Cisco Swank! He’s a super-talented multi-instrumentalist, a Berkeley grad, who makes his own music. I forget how we met, but I think it was in New York. He’s just a whiz kid and a good friend of mine in the jazz community. We had a session and that song came together and he played everything. That’s why I named it that. It was really cool to see him hopping on the drums and then the organ and then the guitar. He spent like an hour and a half on the whole thing. These sessions were very intentional. We didn’t waste any time.

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I believe we might have started something else before, but once we did this song, it just felt right. I’ve been working on Crybaby for about four years and I’d say there are probably four songs out of the 13 that have made it through that whole four years. There’s been a lot of rearranging. In that specific spot where “Cisco’s Song” is, I had a couple of different ideas, but I wanted to honor him.

Obviously, you and Anderson .Paak have a rich history together. What kind of official and unofficial rules governed the Crybaby sessions?

I think the unofficial rule was: do your best and go as hard as you can. Even when you think you’ve done your best, go harder. In the span of four years, I’ve workshopped over 50 songs and I enjoyed them all. I was just trying to elevate how I [could] push until I felt like I said everything I needed to say. I wanted to make sure I didn’t feel like there’s anything missing or anything [that was] still required in the song.

A spoken rule was: We get an opportunity to do what we love, so let’s be grateful and show up with a positive attitude every time we’re in the studio. Every time that I’m with Anderson, whether it’s with my music or working with his or other artists’, I think there’s just a level of gratitude that’s in the room that derives from him. He’s really one of the hardest-working people I know. When I asked him about it, [he was] like, “Well, why wouldn’t I be? These are my dreams, right? Everything I wished for.” I try to take that in every session, even if I’m tired or we’ve been there for hours. These are literally my dreams, so we’re gonna be here till we get that snare sound right.

You also appeared on the new NxWorries album. Were there any songs that you guys had to decide if they would end up on that record versus yours?

No, that’s a big boy album! [ Laughs. ] Those guys have been doing it for a long time. I was just blessed [to be included]. But I will say that I had to f—king fight for me to be on “OutTheWay” — because, at the end of the day, that’s my big bro and I think he wants me to do my best. When I first did the song, he was like, “It’s cool.” But I think he was nervous. He said to me, “You’re already on another song. I don’t know… two songs?”

He kept telling me, “Every time I play it for other people, they’re like, ‘This one’s my favorite.’” I had to really prove my worth in a very humorous, sibling-like way. We have a lot of demos together; there’s a version of “Lockdown” somewhere that I have a verse on. I’m just happy that I got to be on such an iconic album.

This album skews primarily R&B, but we got to know you as an MC. Was that an intentional choice?

I’ve been singing since I was five, so I just wanted to be considered as good a rapper as I’m a singer. I had a chip on my shoulder for so long, but it wasn’t really until Anderson helped me realize that we can do everything. Why wouldn’t you put your best foot forward and showcase your strong suit? I believe that my rap ability is up to par with my singing, but I feel like I catch more ears with my singing voice. So why wouldn’t I sing very beautifully, in hopes that it’ll make people interested in what else I can do?

I thought an R&B album would be a perfect introduction to the huge tapestry of all the different things I want to do in music, you know. I kind of get nervous, that’s why it’s important for me to put “She’s A Bore” on there or “Hot Track” or “Overcast/Overture” because I still like to be myself and sing and rap, but I’m also giving you what you want from me.

Were there any particular pressures that you felt in crafting this album versus your other projects?

I was born in 1996, so I grew up with album rollouts. Loving music my whole life, it’s like, “Wow, I’m on a major label.” That means I have to make major label moves. I think it was December 2022, I had a full 13-track album called Crybaby with a bunch of songs that are not on there anymore, and I played it for Anderson. He was like, “This is good, but it’s not great.” I remember being crushed; I had been dedicating everything to these songs and he told me to dig deeper.

That’s where the “Is It Worth It” idea came from — just me asking myself those questions of, “Do I even want to do this to the extent of being in these rooms I don’t want to be in?”

I knew the gravity of being on a label like Def Jam, and I wanted the music to mirror that, and I think I did it. Songs like “Come Home,” “Is It Worth It,” “It Is What It Is,” and “Bittersweet” are all really strong and took a long time. This didn’t happen in a couple of months, so I just want people to feel the care and the time in the songs.

How do you think this album fits in conversation with your other projects from a thematic standpoint?

I think it’s an evolution and an elevation artistically. I think it’s more introspective. The last album’s called For the World, so I was making music for the world. I think these songs are more like diary entries, it’s not necessarily for the world. If anyone wants to listen, that’s awesome. But this is very personal, and I’m building on my own personal story as a person and an artist.

You are credited as executive producer on this record. How do you understand that term and what did that look like for you during the album-making process?

I think executive producing this album for me meant that I was a part of every single process. I can’t wait for the day when I can make an album and it’s like “Okay, I recorded it bye!” But I was there every day like, “Move this there. Turn me up here. Move me to the right a little bit. We need something like this, I’m going to call my friend. He’s going to come put violin. Who can I add [to] this? Now I need to call my homegirls, get some backing vocals.”

I was there in the mastering process, the mixing process. I saw some songs get mastered by tape. We didn’t choose those, but it was really cool to be in the room watching it. I wanted to make sure I was an integral part of every single aspect of the album. Even [with] the art direction, I’ve had that album cover for four years. Ever since the artist drew it, I knew I was going to work with it and have the picture inspire some of the songs. I was the catalyst and the crux to bridge the gap from the old Rae Khalil to coming into a major label and what that looks like.

Not everyone can say they have their favorite rapper on their major label debut album! What was it like working with Freddie Gibbs?

I originally had a different rapper on “Carpinteria,” and he was just lazy. The recording that he sent me… the audio was just shit. I asked him to redo it and he left me on seen. It was just a bunch of bullshit. I enjoy your music, but I’m not gonna put up with you not being communicative. I remember sharing that with Anderson and being so bummed out and crying, and he was like, “We’ll just get Freddie to do it.”

I just didn’t think it was real. I remember teasing him like, “Yeah, I remember you said that. We’ll see!” And then all of a sudden, it happened. I was like, “Oh my God, oh man, you made my dreams come true.”  I’ve been able to hang out with him more frequently, and he’s just so fun. I’m such a fan girl, so I’m always [asking him questions]. He blessed me with a beautiful verse. It was supposed to be a short verse, but he did such a long one. Apparently, he really loved the song!

Do you have any plans to tour the album?

Oh, that’s the dream! I would hope so. My manager’s telling me Billie Eilish is going on tour — and that’s really far-fetched, but if I could open up for her, I think that would open up a lot of doors. That’s who I have my eye on, you know. Hopefully, she reads this article.

Are you happy with the major label version of Rae Khalil?

I am so happy. This is coming from the girl who started rapping when Acid Rap was popular. I was like, “I’m never gonna sign!” [ Laughs .] I had no idea what I was talking about. There’s a reason why Beyoncé is still at Columbia. I’m that type of artist [who wants] to build a working symbiotic relationship [with a label]. It’s a business at the end of the day, so I want to do well in the business aspect so much so that I have more creative freedom in the music aspect. I love Tunji. I love Def Jam. I’m just really happy to be where I am.

I’m a little nervous. I started putting music on SoundCloud in high school, so to be at this point is really cool. I’m approaching everything with open arms.

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