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10 Songs From The Late '80s That Kicked Off R&B and Rap Collaborations

Rapper Heavy D out on the town circa 1989 in New York City, New York.

Photo by Michael Ochs Archives via Getty Images.

10 Songs From The Late '80s That Kicked Off R&B and Rap Collaborations

Rap and R&B go hand-in-hand. But this wasn't always the case. Let's go back to the late '80s to look at the early history of R&B and rap collaborations.

This article has been handpicked from the Okayplayer editorial archives and included in our Hip Hop 50 collection as a noteworthy inclusion to the genre's rich and diverse narrative. The article has been edited for context to ensure its accuracy and relevance.

The year 1988 was when R&B’s sonic aesthetic officially switched to New Jack Swing. This occurrence sent a ripple effect throughout black music. Prior to 1988, R&B kept the rising influence of New Jack Swing at bay while traditional R&B/soul artists still dominated the Hot Black Singles and Top Black Albums charts. The combination of the Minneapolis Sound, spearheaded by Prince, Jimmy Jam & Terry Lewis, Andre Cymoné and Jesse Johnson, and innovative production from the likes of Full Force, Nick Martinelli, Larry Blackmon, Foster & McElroy, L.A. & Babyface, and more, had a hand in changing the sound of black music forever.

This sea change opened the door to R&B artists finally doing collaborations with rappers. Many of black music’s gatekeepers weren’t fond of rap, including Don Cornelius, Frankie Crocker, and Donnie Simpson. Older Black music executives never embraced the genre, but when they saw how many rap singles and rap albums topped the chart in 1988 they began to suggest established R&B acts collaborate with rappers to stay relevant and make hits on black radio both old and young fans could enjoy.

Most early R&B/rap collaborations were either forced or orchestrated by record executives. Very few were organic, but the success of these early pairings ensured they’d become standard as the years passed.

A couple of things to note: I won’t be including songs where the artist themselves rapped either part of or an entire verse themselves (example: Bobby Brown on “Don’t Be Cruel” or Vanessa Williams on “The Right Stuff”). I'm also leaving out early forced collaborations, likeChaka Khan’s cover of Prince’s “I Feel For You” with Grandmaster Melle Mel. Chaka hated it and it didn’t lead to more pairings of the sort.

With that being said, here are the first 10 R&B/Rap collaborations on record.

Rick James featuring Roxanne Shante - “Loosey’s Rap” (1988)

10 Songs From The Late '80s That Kicked Off R&B and Rap CollaborationsCover of Rick James, Roxanne Shante and Big Daddy Kane's 1988 single, "Loosey's Rap."Source: Reprise Records

Rick James left Motown after the failure of his 1986 LP The Flag, and signed with Reprise/Warner for his 1988 offering Wonderful. Rick hadn’t had a hit since his 1985 project Glow, so Warner paired him with Roxanne Shante of the Juice Crew. Cold Chillin’ was on Warner Bros, and because of the success of Big Daddy Kane-penned albums for people like Biz Markie, a collabo seemed like a definite home run.

Rick James begrudgingly agreed. On the single sleeve, both Roxanne Shante & Big Daddy Kane are credited in small type so as to not deter rap-hating radio programmers/DJ’s or older music fans from playing or purchasing it. The song began to take off. Inexplicably, Roxanne Shante was nowhere to be seen in the video once it hit BET and MTV. In August 1988, “Loosey’s Rap” hit number one on the Hot Black Singles and would be the last number one of Rick James’ music career. Sadly enough, he never once acknowledged Roxanne Shante’s role in making the song a hit. The success of this experiment ensured there’d be more collaborations with rappers in the future.

Midnight Star featuring Ecstacy (of Whodini) - “Don’t Rock The Boat” (1988)

10 Songs From The Late '80s That Kicked Off R&B and Rap CollaborationsCover of Midnight Star and Ecstasy's 1988 single, "Don't Rock The Boat."Source: Sound of Los Angeles Records

Midnight Star were in the process of starting over. They lost their hitmaking songwriters/producers in founding duo Reggie & Vincent Calloway after their smash 1986 LP Headlines, once the accompanying tour ended. They needed a hit lead single to provide momentum for their album in a foreign black music landscape in 1988. James Brown was made relevant again by production from Full Force. And a rapper feature on Rick James’ first single resulted in a hit so SOLAR’s Midnight Star tapped Ecstacy from Whodini to appear on “Don’t Rock The Boat”.

In this particular case, Ecstacy wasn’t going to alienate their core fan base or make consumers or radio DJ’s shy away from a Midnight Star song. Further proven by the fact they didn’t give Ecstacy’s name the small type treatment on the single cover. As a result, “Don’t Rock The Boat” peaked at number three on the Hot Black Singles chart in November 1988 but never cracked the Hot 100. This ensured that more established Black music acts would employ a rapper in hopes of securing a hit as the sound of R&B switched over to New Jack Swing.

Levert featuring Heavy D - “Just Coolin’” (1988/89)

10 Songs From The Late '80s That Kicked Off R&B and Rap CollaborationsCover of Levert and Heavy D's single, "Just Coolin'"Source: Atlantic Records

In the case of Levert, both Gerald Levert and Marc Gordon were young enough to have grown up with Rap. In fact, Levert was adept at making hits as the sound of R&B shifted (their 1987 jam “Casanova” being proof of this.) Just Coolin’ is the album-defining cut, the titular song. Heavy D wasn’t placed on here as an afterthought and no A&Rs or executives had to force Levert into collaborating with him. If anything, “Just Coolin’” didn’t sound too far off from the Eddie F, Teddy Riley or Marley Marl production Hev would’ve rapped on for one of his own singles.

As to be expected, “Just Coolin’” hit number one on the Hot Black Singles charts in March 1989 but never crossed over to the Hot 100, further cementing the inevitability of R&B acts doing more organic collaborations with rappers or raps groups. More importantly, Hev appeared in the video and performed the song live with Levert on multiple occasions.

Al B. Sure! featuring Slick Rick - “If I’m Not Your Lover (Remix)” (1989)

10 Songs From The Late '80s That Kicked Off R&B and Rap CollaborationsCover of Al B. Sure and Slick Rick's 1989 single "If I'm Not Your Lover" Source: Warner Music Group

Al B. Sure! had come off the 1988-89 Heart Break Tour with New Edition and Bobby Brown, a bonafide superstar. His final single off In Effect Mode was “If I’m Not Your Lover," the remix featured Slick Rick whose voice he imitated on “Off On Your Own (Girl).” On the single cover you practically needed a magnifying glass to see Slick Rick’s name as the featured artist. Surprising no one, the single peaked at number two on the Hot Black Singles charts in May 1989 but again failed to cross over to the Hot 100. We were only about a year deep into the world of R&B and Rap collaborations but they were about to become more frequent between spring and summer 1989. There was no video, but Slick Rick did perform the song with Al on multiple televised occasions.

O’Jays featuring The Jaz - “Have You Had Your Love Today?” (1989)

Cover of The O'Jay's 1989 album, Serious. Source: EMI

Gerald Levert and Marc Gordon of Levert were responsible for teaming the legendary O’Jays up with an upcoming MC and EMI labelmate The Jaz. The O’Jays have been hitmakers since 1963, but in a post-New Jack R&B climate, Eddie Levert put his trust in his son Gerald to craft the sound that would continue their streak of success.

Of course, the pairing between the O’Jays and fast rap aficionado The Jaz resulted in yet another No.1 hit on the Hot Black Singles chart in June 1989. Stop me if you’ve heard this one before, but the song failed to cross over to the Billboard Hot 100. Nonetheless, it helped the O’Jays’ 1988 LP, Serious, become yet another hit album on their already impressive resumé.

Joyce “Fenderella” Irby featuring Doug E. Fresh - “Mr. DJ” (1989)

Cover of Fenderella and Doug E. Fresh's 1989 single, "Mr. DJ."Source: Motown Records

Joyce Irby broke from her old group Klymaxx in hopes of finding solo success on Motown. Her lead single featured human beatbox legend, Doug E. Fresh, leader of the Get Fresh Crew. Doug’s album The World’s Greatest Entertainer had set the black music charts ablaze so he was a hot commodity when he teamed with Joyce. Doug E. Fresh & The Get Fresh Crew’s “Keep Risin’ To The Top” was one of the biggest songs of the previous summer and they fully expected Doug to deliver another summer smash. The end result was an uptempo New Jack Swing-flavored dedication to the DJ off her debut solo LP Maximum Thrust.

“Mr. DJ” peaked at number two on the Hot Black Singles charts in June 1989, usually battling the O’Jays own hit song with a rap feature for the number one spot.

Jody Watley featuring Eric B. & Rakim - “Friends” (1989)

Cover of Jody Watley and Eric B. & Rakim's 1989 single, "Friends."Source: MCA Records

Jody Watley’s self-titled 1987 solo debut LP went Platinum and yielded four hit singles. She was a triple threat on the R&B, pop, and dance charts, alongside Janet Jackson and Madonna. Her sophomore album, Larger Than Life, opened with another big single “Real Love” which would go gold out the gate. Jody Watley was a crossover star at the time she dropped her follow up single, a collaboration with MCA labelmates Eric B. & Rakim. It was the perfect storm, a dream scenario. An established R&B, pop and dance hitmaker teamed with one of the most widely respected rap acts would potentially result in a smash.

The single was released in April 1989 and steadily rose up the charts. The video became popular on both BET and MTV, garnering a coveted spot on Donnie Simpson’s Video Soul Top 20 countdown. “Friends” peaked at number three on the Hot Black Singles chart in July 1989, but the big news is it managed to do what no previous R&B/Rap collaboration had done before: crossover to the Hot 100 charts. “Friends” reached number nine on the Billboard Hot 100 in August 1989. When Jody Watley performed “Friends” on The Arsenio Hall Show, Eric B. & Rakim weren’t present but she performed Rakim’s verse effortlessly. This monumental event in R&B/Rap collaboration history has largely gone overlooked close to 30 years after the fact.

Quincy Jones - “Back On The Block” (1989)

Cover of Quincy Jones' 1989 single, "Back on the Block." Source: Warner Music Group

Music industry legend and super producer Quincy Jones released his first album since 1981’s The Dude in August 1989 titled “Back On The Block.” One of the most groundbreaking things about Back On The Block was Quincy Jones’ willingness to include MCs on his album, not just as featured performers hand-picked to make him a hit single but as crucial contributors to his project. His son QD III was a rap fan and a music producer in his own right and put his father on to the genre. Unlike many of his contemporaries and frequent collaborators, including Ray Charles, who didn’t care much for rap music or rappers, Quincy knew the best way to incorporate what they do into his compositions and help rap get the much-needed critical praise it deserved.

Quincy Jones tapped Grandmaster Melle Mel,Kool Moe Dee, and Ice Tto contribute his comeback album that opens with QD III and Quincy Jones going back and forth spitting Big Daddy Kane-helmed rhymes. Even though rap was being recognized by the American Music Awards and Grammys and Billboard introduced the Top Rap Songs chart back in March 1989, the genre still faced resistance from those who didn’t consider it a legitimate art form. Back On The Block helped to change that.

Rappers were included in Quincy Jones’ February 10th 1990 appearance on Saturday Night Live. This was huge. Having several MCs appear in the critically acclaimed 1990 Quincy Jones documentary Listen Up: The Lives Of Quincy Jones was an even bigger gesture. Most important was having these same rappers appear on the album intro, title track and song “Jazz Corner Of The World (Introduction To Birdland)." Back On The Block won Album Of The Year at the 1991 Grammy Awards and the song won the Grammy Award for Best Rap Performance By A Duo Or Group. This album’s mainstream and critical success did a wealth of good for rap music and helped to further legitimize the art form even in the eyes of its detractors.

Foster & McElroy featuring MC Lyte - “Dr. Soul” (1989)

Cover of Foster & McElroy's 1989 single, "Dr. Soul."Source: Atlantic Records

Denzil Foster and Thomas McElroy are one of the most underrated songwriting and production duos in modern black music history. They’ve been the team behind the successes of Timex Social Club, Club Nouveau, Tony! Toni! Toné! and EnVogue. But back in September 1989 they released an album called FM2 on Atlantic Records. Their second single off the album featured labelmate MC Lyte whose sophomore album, Eyes On This, dropped the week after theirs did. In any event, the New Jack Swing dance track “Dr. Soul” peaked at number ten on the Hot Black Singles Charts in December 1989, becoming the biggest hit off the album and further proving the drawing power of an MC on an R&B track.

Janet Jackson featuring Heavy D - “Alright” (1990)

Cover of Janet Jackson and Heavy D's 1990 single, "Alright."Source: A&M Records

Janet Jackson’s 1986 album Control was a landmark release in modern black music that forever changed the trajectory of R&B. Her 1989 follow up, Janet Jackson's Rhythm Nation 1814, re-established her place among the elite in her field as the album produced hit after hit. “Miss You Much," “Rhythm Nation” and “Escapade” were all massive smashes and her fourth single “Alright” was no exception. Not only was there a remix featuring a verse from Heavy D but he was also featured in a version of the song’s video that received a ton of play on BET and MTV.

The Heavy D featured version of “Alright” peaked at number two on the Hot Black Singles chart and hit number one on the Dance charts in May 1990 and topped out at number four on the Hot 100 in June 1990. What made this particular R&B/rap collabo different was it would be the last one before Vanilla Ice released “Ice Ice Baby,” which would become the first rap song to reach number one on the Billboard Hot 100 charts in November 1990.

After 1990, all bets were off. Soon R&B artists were featured on rappers’ songs to make them hot as opposed to the other way around.


Dart Adams is Boston-based creative who has written for NPR and Producers I Know. Follow his latest and greatest @Dart_Adams on Twitter.