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Rappers and R&B singers weren’t always requisite bedfellows. While singers like Bobby Brown faced little to no backlash when sprinkling bars between notes, rap listeners initially weren’t as forgiving. Simply put, in a genre obsessed with street credibility and hardcore imagery, dabbling in R&B equaled selling out.

Back in 1989, Eric B. & Rakim’s guest appearance on Jody Watley’s friends—one of rap’s first forays into R&B territory— didn’t go over so well; perhaps because Rakim—an MC revered for his superior lyricism on tracks like “I Ain’t No Joke” and “Microphone Fiend”— delivered two watered down verses on the track. “When Rakim did [‘Friends,’ with Jody Watley], we were all confused…” legendary mixtape DJ, Ron G, told XXL in the August 2009 issue (The Hip-Hop Soul Issue). I was like, “How do you go from hard edge to soft edge and you’re a hard artist?”

By the early 1990s, Rap and R&B collaborations were commonplace. The Notorious B.I.G. dropped eight bars on Mary J Blige’s “Real Love” Remix and Wu-Tang Clan’s Old Dirty Bastard, Method Man and U-God made an appearance on SWV’s “Anything” Remix.

Now 20 years after Rakim plunged into uncharted waters, the line between rap and R&B has become significantly blurry. Still, MCs like Fabolous, who has become R&B’s go-to guest collaborator over the years, spits lyrical verses whether working with The-Dream or Jay-Z. “I’m one of the few artists that is able to do that and still hold his credibility and also not lose his edge as far as being creative and lyrical,” Fab told XXL during the behind the scenes shoot for the August 2009 cover. “At the same time too ’cause when I attack a joint even R&B-wise, I go at it the same way I would go at a hip-hop joint but just more stay in the subject of the R&B song.”

Fab’s not alone. MCs like Jay-Z, Ludacris and Jadakiss have consistently recorded stellar verses on R&B tracks throughout their careers. Here, ranks the Top 25 best rap performances on an R&B song.—Compiled by Matt Barone, Carl Chery, Mike Delfin, Kamaria A. Gboro, Clover Hope, John Kennedy, Rob Markman, Patresha Williams and Taiia Smart Young

25. Keith Murray on R. Kelly’s “Home Alone,” R. (1998)

24. Heavy D on Monifah’s “I Miss You,” Moods…Moments (1996)

23. Styles P on Akon’s “Locked Up,” Trouble (2004)

22. Big Boi on Missy Elliot’s “All N My Grill,” Da Real World (1999)

21. Skillz on Aaliyah’s “Are You That Somebody” Remix, Are You That Somebody Remix 12″ (1998)

20. Lil Wayne on Destiny’s Child’s Soldier,” Destiny’s Fulfilled (2004)

19. Mase on 112’s “Love Me,” Room 112 (1998)

18. LL Cool J on Mary J Blige’s “Mary Jane (All Night Long)” Remix, Mary Jane (All Night Long) 12″ (1995)

17. Ludacris on Ciara’s “Ohh,” Goodies (2004)

16. Jadakiss on Usher’s “Throwback” Remix, Confessions Special Edition CD (2004)

15. Kanye West on Dwele’s “Hold On” Remix, Hold On Promo 12″ (2004)

14. Common on Erykah Badu’s “Love of My Life (An Ode to Hip-Hop),” Brown Sugar (Original Soundtrack) (2002)

13. Big Pun on Brandy’s “Top of the World Part II,” Top of the World Part II CD Single (1998)

12. Lil’ Kim on Mary J Blige’s “I Can Love You,” Share My World (1997)

11. Nas on Allure’s “Head Over Heels,” Allure (1997)

10. Andre 3000 on Lloyd’s “You” Remix, You 12″ (2007)

9. Fabolous on Lil’ Mo’s “Superwoman Pt.II,” Based on a True Story (2001)

8. Rakim on Truth Hurts’ “Addictive,” Truthfully Speaking (2002)

7. Smiff-N-Wessun on Mary J Blige’s “I Love You” Remix, I Love You 12″ (1995)

6. Foxy Brown on Case’s “Touch Me, Tease Me,” Case (1996)

5. AZ on D’Angelo’s “Lady,” Lady 12″ (1996)

4. The Notorious B.I.G. on Mary J Blige’s “Real Love,” What’s the 411? (Remixes) (1993)

3. Jay-Z on Mya’s “The Best of Me Part 2,” Best of Me 12″ & DJ Clue-Presents: Backstage-Mixtape (Music Inspired By The Film (2000)

2. Raekwon & Ghostface on Jodeci’s “Freak’n You,” Get On Up 7″ CD Single (1995)

1. The Notorious B.I.G. on Total’s “Can’t You See,” Total (1995)

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