Rolling Ray Compares Drake & Sexyy Red To Biggie & Lil Kim

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Notorious B.I.G. AKA Biggie Smalls Receives Billboard Music Award.
Rapper Notorious B.I.G. AKA Biggie Smalls (Christopher Wallace) joined by Sean (Puffy) Combs and Lil' Kim receives Billboard Music Award on December 6, 1995 at The Coliseum in New York City, New York. (Photo by Larry Busacca/Getty Images)
The reality television and social media personality thinks that folks aren't ready for this comparative conversation.

Whenever there's a big bond between a male rapper and a female rapper, our hetero-centric and gossip-loving culture tends to ship them on impact. After all, there's plenty of precedent for this kind of relationship to develop, as well as many examples of it not happening or turning out pretty sour. Moreover, rapper, reality TV star, and social media personality Rolling Ray brought forth a pretty interesting theory and interpretation on Twitter last Sunday (March 17). "Hear me out... Drake is endorsing Sexy Redd like Biggie did with Lil Kim! But yall not ready for that conversation!" he shared with his followers. "& they situationship will get deeper! Watch," Ray added on Instagram, captioning a screenshot of his tweet.

Furthermore, for those unaware, Drake and Sexyy Red have quite the close bond these days, as they've performed together on tour and have at least one collab under their belt. The "Rich Baby Daddy" duo, though, have also been pretty cheeky when it comes to their relationship. They've joked about being involved sexually, being each other's muse or spouse, and about the 6ix God being... well, a rich abby daddy. Not only that, but as their stardom continues to build and progress, we have a feeling they'll stay on each other's good side.

Rolling Ray's Take About Sexyy Red, Lil Kim, Drake & Biggie

Meanwhile, some younger readers might not know the connection between Lil Kim and Biggie. These two childhood friends from Brooklyn became close artists under Bad Boy Records, and did have a romantic fling throughout The Notorious B.I.G.'s tragically shortened life. To this day, Kim continues to pay tribute to him as a far greater figure than the sum of the lenses through which she viewed their versatile bond. As such, Rolling Ray is insinuating that Drake and Sexyy Red's connection runs much deeper than joking about them being together.

But it's important to note that he also has a certain bias in this situation, as he insulted the "SkeeYee" MC not too long ago for her looks. Regardless, do you think that these are two comparable MC-femcee pairings in hip-hop or is there no basis at all? Whatever the case, drop your thoughts down in the comments section below. Also, stick around on HNHH for the latest news and updates on Biggie, Lil Kim, Sexyy Red, and Drake.

About The Author
Gabriel Bras Nevares is a staff writer for HotNewHipHop. He joined HNHH while completing his B.A. in Journalism & Mass Communication at The George Washington University in the summer of 2022. Born and raised in San Juan, Puerto Rico, Gabriel treasures the crossover between his native reggaetón and hip-hop news coverage, such as his review for Bad Bunny’s hometown concert in 2024. But more specifically, he digs for the deeper side of hip-hop conversations, whether that’s the “death” of the genre in 2023, the lyrical and parasocial intricacies of the Kendrick Lamar and Drake battle, or the many moving parts of the Young Thug and YSL RICO case. Beyond engaging and breaking news coverage, Gabriel makes the most out of his concert obsessions, reviewing and recapping festivals like Rolling Loud Miami and Camp Flog Gnaw. He’s also developed a strong editorial voice through album reviews, think-pieces, and interviews with some of the genre’s brightest upstarts and most enduring obscured gems like Homeboy Sandman, Bktherula, Bas, and Devin Malik.
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