These days, the line between Hip Hop and pop is nearly invisible. In many cases, rap artists routinely drive the sound and the success of global pop culture. At the same time, pop stars have long looked to our culture for credibility, swagger, and that extra edge to push their music beyond traditional audiences.
The relationship is symbiotic. Rappers bring edge, rhythm, and cultural capital, while pop singers provide hooks, mass appeal, and crossover star power. When they link up, the results often dominate radio, streaming playlists, and TikTok feeds alike. These collaborations aren’t just songs — they’re milestones that showcase how deeply the genres are woven together.
Here, we spotlight songs proving how these two entities build connections through memorable collaborations. It all adds to the blurring of genre boundaries and shapes the mainstream sound for generations.
1. Baby – Justin Bieber feat. Ludacris
Bieber’s breakout hit proved Hip Hop was willing to embrace him early. With Ludacris jumping on the track, “Baby” became a pop-rap phenomenon, turning a teen idol into a global star and cementing hip hop’s role in his rise.
2. Bad Blood (Remix) – Taylor Swift feat. Kendrick Lamar
Taylor surprised the industry by linking with Kendrick for the remix to “Bad Blood.” His sharp verses gave the pop anthem Hip Hop weight, while the star-studded video premiere turned the collab into a full-blown cultural event.
3. Boys (The Co-Ed Remix) – Britney Spears feat. Pharrell Williams
Pharrell and Chad Hugo of The Neptunes gave Britney’s “Boys” a new spark with this remix, released on the Austin Powers in Goldmember soundtrack. Pharrell’s feature and production helped push Britney deeper into Hip Hop’s orbit at the height of her pop reign.
4. Dirrty – Christina Aguilera feat. Redman
Christina flipped her image with “Dirrty,” teaming up with Redman and producer Rockwilder for a club-ready anthem. The lead single from Stripped shocked pop audiences but won Hip Hop credibility, cementing her as an artist unafraid to push boundaries alongside rap heavyweights.
5. Suit & Tie – Justin Timberlake feat. JAY-Z
After a six-year hiatus, Justin Timberlake returned with “Suit & Tie,” linking with JAY-Z and longtime collaborator Timbaland. The classy comeback single fused soul, pop, and Hip Hop, with Hov’s verse elevating it into a polished masterpiece.
6. &burn – Billie Eilish feat. Vince Staples
Billie’s first major Hip Hop crossover came with “&burn,” a darker reimagining of her single “watch.” Vince Staples’ verse matched her moody delivery, giving the track a sharper edge and signaling her early embrace by the rap community.
7. Right There – Ariana Grande feat. Big Sean
Ariana carried her R&B-inspired debut into Hip Hop territory with “Right There,” pairing smooth vocals with Big Sean’s playful verse. Much like the Mac Miller-assisted “The Way,” this Yours Truly standout helped solidify her chemistry with rap collaborators early in her career.
8. Dark Horse – Katy Perry feat. Juicy J
Katy Perry’s trap-inspired single became an unexpected Hip Hop crossover, with Juicy J delivering one of the most memorable guest verses of the 2010s. The collaboration shot to No. 1 on the Hot 100, proving how seamlessly pop hooks and rap features could dominate the charts.
9. B**ch I’m Madonna – Madonna feat. Nicki Minaj
Madonna’s Diplo-produced single turned into a wild party anthem, with Nicki Minaj’s fiery verse elevating its chaos. The track’s star-packed video added to its spectacle, proving the Queen of Pop could still thrive alongside Hip Hop royalty.
10. My Darlin’ – Miley Cyrus feat. Future
On Bangerz, Miley linked with Future for “My Darlin’,” a ballad built around the classic “Stand By Me.” Produced by Mike WiLL Made-It, the track blended pop melodrama with Auto-Tuned rap vulnerability, showcasing the duo’s chemistry in heartbreak mode.
11. Rich Girl – Gwen Stefani feat. Eve
Following Eve’s “Blow Ya Mind,” Gwen Stefani teamed with the Philly emcee once again on “Rich Girl,” a Dr. Dre-produced smash from Love. Angel. Music. Baby. Borrowing from Fiddler on the Roof, the track mixed Gwen’s theatrical pop with Eve’s stylish rap verses.
12. Havana – Camila Cabello feat. Young Thug
Camila Cabello’s breakout solo hit paid homage to her Cuban roots while enlisting Young Thug for a slick Atlanta rap contrast. The sultry track soared to No. 1 on the Billboard Hot 100, cementing her post-Fifth Harmony stardom.
13. All Night Long – Demi Lovato feat. Missy Elliott and Timbaland
Opening Demi Lovato’s Unbroken, this Miami-recorded party anthem brought unexpected Hip Hop energy. Timbaland handled the production and ad-libs, while Missy Elliott slid in with a playful verse that gave the pop track undeniable crossover flair.