The Rise Of The Featured Rapper In Pop Music

Illustration by Mark Alan Stamaty.

Twenty-five years ago, in late July 1990, the Billboard Hot 100 welcomed a No. 1 single that, while very mediocre, would turn out to be quietly historic: the first of a new breed of chart-topper.

The song was “She Ain’t Worth It,” a one-off pairing between Hawaiian pop crooner Glenn Medeiros andâ€"dropping in more than halfway through with a rap bridgeâ€"New Jack Swing megastar Bobby Brown. Forgettable as it was, “Ain’t” holds two distinctions: It’s the first chart-topping sing-and-rap two-artist pairing in Billboard history, and it’s alsoâ€"with a couple of asterisks**â€"the formal debut of the word “featuring” on a No. 1 hit.

It is hard to overstate how popular that word has become on the charts over the last quarter-century. On the Hot 100 for the week ending July 25, 2015, the word “featuring” appears no fewer than 29 times. Along with a couple of instances of “with,” & an ampersand or two between acts who do not normally team up and are not formally duetting, fully one-third of the chart consists of one-off collaborations.

The song that started all this was neither exceptionally creative nor unprecedented. Prior to “She Ain’t Worth It,” a handful of sing-and-rap pairings fell short of Billboard’s No. 1 spot. But Medeiros’ hit went the distance because it had genre crossover baked into itâ€"its very awkwardness made it an effective hybrid.

According to Fred Bronson’s Billboard Book of No. 1 Hits, the pairing was suggested after Medeiros had already completed a recording of the song, an up-tempo follow-up to his 1987 top-20 ballad “Nothing’s Gonna Change My Love for You.” But then Rick James, a friend of the head of Medeiros’ label, suggested that the genteel young singer try working with Brown, arguably the top artist in pop at the time; Brown’s Don’t Be Cruel was the top-selling album of 1989, and on his most recent hit, the No. 2 summer ’89 smash “On Our Own” from the soundtrack to Ghostbusters 2, Bobby had even rapped. In the studio with Medeiros, on the spot, Brown wrote a quick eight-bar bridge. (What, you don’t remember its classic lyric? “The girl is jazzy, but she’s nothing but TROUBLE.”) With a snatch of Bobby’s rap at the start of the record and all of 20 seconds in the middle, “She Ain’t Worth It”â€"Glenn’s bid for pop-pinup stardomâ€"was complete.

When “Ain’t” reached No. 1 in the summer of 1990, it mostly affirmed that Brown was at the apex of his imperial period, able to turn even this twaddle into gold. (Medeiros never returned to Billboard’s Top 20. He is now the head of a prestigious private school in his native Hawaii.) But it also affirmed the commercial potency of both the featured-artist credit and its artistic sibling, the rap bridge, as the vector of pop crossover. If 20 seconds of Bobbyâ€"not even an actual rapperâ€"dropping eight bars could help non-threatening boy Medeiros top the charts, the warbler-and-rhymer possibilities were endless. Arguably, this is as important a record to the hybridization of pop and rap as the storied “Walk This Way” by Run-DMC and Aerosmith.

When “She Ain’t Worth It” reached No. 1, it affirmed that Bobby Brown was at the apex of his imperial period, able to turn even this twaddle into gold.

Mind you, it’s not like artist pairings on hit singles didn't exist before 1990, or even before hip-hop. If you go about a quarter-century in the other direction from “She Ain’t Worth It,” to the charts of the 1960s, you will find plenty of collaborative hits on the Hot 100. The Crystals’ 1963 No. 1 “He’s a Rebel” features lead vocals from another Phil Spector protégée, Darlene Love. The Temptations’ 1965 No. 1 “My Girl” was not only written by rising Motown star Smokey Robinson, its backing track was recorded by him, as well. (Indeed, the entire Motown hitmaking system was built by Berry Gordy around collaboration.) Bob Dylan’s 1965 classic “Like a Rolling Stone,” a No. 2 hit, showcases guitar by Mike Bloomfield, axeman from the Paul Butterfield Blues Band. Elvis Presley’s 1969 “comeback” chart-topper “Suspicious Minds” features very audible vocals by country’s Ronnie Milsap and Muscle Shoals vocalist Jeanie Greene.

The difference between then and now is none of these celebrated ’60s musicians were listed as featured artists on these singlesâ€"Robinson earned only songwriters’ credit; Bloomfield, Milsap, and Greene were liner-notes fine print; Love wasn’t credited at all. In rock’s early years, even when pop acts relied on an army of collaborators, the music industry perpetuated the myth of the single, self-contained “artist” as the face of each hit.

So what happened between the dawn of rock ’n’ roll and the turn of the 21^st century that expandedâ€"some might say bloatedâ€"songs’ above-the-line credits? As a mongrel form from birth, rock ’n’ roll has always been about mashing up genres and formats which are rooted in notions of gender, race, and culture. But it took the rise of hip-hop, a more conspicuously hybridized art formâ€"where the team-up of rappers, DJs, and backing tracks is text, not subtextâ€"to put the featured performer at center stage. Maybe it’s a drag for Billboard magazine’s chart-layout department, but the modern approach to artist credit is probably the way it should have been all along.

The problem of how to credit artist collaborators goes all the way back to the dawn of charts. You can see it on Billboard’s very first recorded-music survey, which coincidentally is celebrating an anniversary this weekâ€"75 years ago, the week of July 27, 1940, the magazine began publishing a “National List of Best Selling Retail Records.” And that very first Top 10 listâ€"one of many precursor charts to the Hot 100â€"was topped by a collaboration of sorts whose lead vocalist went uncredited. Perhaps you’ve heard of this crooner: one Frank Sinatra, who sang lead on “I’ll Never Smile Again,” a single by big-band leader Tommy Dorsey. Actually, Young Blue Eyes did receive his propers on the label of the 78-RPM record, which read “Tommy Dorsey and his Orchestra” and, in very small print at the bottom, “Vocal refrain by Frank Sinatra and The Pied Pipers.” But the entry on Billboard’s very first pop chart simply read “Tommy Dorsey.” Sinatra was surely the reason millions were buying that shellac platter, but to the industry Dorsey was the nominal performerâ€"bandleaders were to the pre-rock era what star DJs are to today. If Dorsey was the Calvin Harris of his time, Sinatra was his Rihanna.

Teen-beloved stars like Sinatra would do better in the rock era, when bandleaders generally took a backseat to pop idols. But song credits didn’t get any less opaque over the next couple of decades. From 1958, when Billboard premiered the Hot 100, through most of the 1960s, no chart-topping song listed a featured performer. Even the word “and” was reserved for permanent duos, established singer-and-the-blanks combos or, occasionally, a nose-to-nose vocal duet between performers of equal stature.