Feat. Don’t Fail Me Now: The rise of the featured rapper in pop music.

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 and—dropping in more than halfway through with a rap bridge—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 also—with a couple of asterisks**—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 it—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”—Glenn’s bid for pop-pinup stardom—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 Bobby—not even an actual rapper—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.

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 singles—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 21st century that expanded—some might say bloated—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 form—where the team-up of rappers, DJs, and backing tracks is text, not subtext—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 week—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 list—one of many precursor charts to the Hot 100—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 performer—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.

There was just one exception in the ’60s, a sort of proto–featured credit, on a No. 1 hit, and it involved the act that was the exception to a lot of rules: the Beatles. Their 1969 single “Get Back”—the 17th of the Fab Four’s record 20 No. 1s on the Hot 100—sports the credit “The Beatles with Billy Preston.” This was, to say the least, a notable achievement for the then–barely known Preston, who was still a couple of years away from launching his own career as a frontman. Notably, Preston doesn’t sing on “Get Back,” but he performs the irresistible keyboard solo that bridges the song’s first and second verses. What inspired the Beatles to give Preston a formal credit, since prior guest performers like Eric Clapton or David Mason had gone unmentioned, remains a mystery—it was likely because the Beatles were friends of Preston’s dating back to the live-revue circuit of the early ’60s, and stories have long circulated that the group briefly considered adding him as a member. But from a music-business perspective, what made the “Get Back” credit prophetic and apt was that it involved a black R&B performer supporting a white rock group—the very model of genre crossover that would take over the industry in the age of hip-hop.

Still, even after Preston’s turn in the spotlight, featured credits remained scarce through the 1970s—mind-boggling, considering some of the team-ups hitting the charts at the time. Carly Simon’s 1972–73 No. 1 hit “You’re So Vain” features backing vocals by none other than Mick Jagger—and yet the label of Simon’s single makes not a mention of Jagger. (As with many men, the song wasn’t really about him.) Another rock eminence, John Lennon, sang backup on No. 1 hits by two of his buddies: Elton John’s strange 1974–75 cover of Lennon’s Beatles song “Lucy in the Sky With Diamonds” (that’s Lennon singing and playing guitar on the song’s reggae break); and David Bowie’s 1975 pop-and-B crossover track “Fame.” (That’s Lennon punctuating Bowie with a squeaky “Fame!” in a high-pitched voice.) Does the erstwhile Beatle appear on the label of either 45? Nope and nope. For his part, Elton John sang backup on his friend Neil Sedaka’s 1975 No. 1 “Bad Blood” (no relation to the recent Taylor Swift song), and he, too, kept his name off the label.

If any form of ’70s music should have sported prominent featured credits, it’s disco, a producer-driven medium that showcased black and female vocalists for crossover consumption. And yet, the industry’s emphasis on lone-wolf performers held firm on the charts. In 1978, Australian pop singer Samantha Sang reached No. 3 in the U.S. with the midtempo disco ballad “Emotion,” a song that for all the world sounds like a Bee Gees song. That’s because Barry Gibb wrote it and sings in his patented falsetto on the chorus. But on this hit, as on the many hits Barry produced and performed on for his brother Andy, the bearded disco Jesus disappeared into the fine print.

By the ’80s, hip-hop finally emerged as a recorded medium, led by the Sugarhill Gang’s “Rapper’s Delight” (a song that probably should have included a prominent “featuring Chic” credit). Early on, rap made some use of the featured credit: Grandmaster Flash and the Furious Five’s 1982 single “The Message” name-checked both rapper Melle Mel and producer Duke Bootee on the label. And on their 1981 single “The Showdown,” the Sugarhill Gang made the artist credit part of the show: the song is officially by “The Furious Five Meets Sugarhill Gang.” Still, for most of rap’s first decade, most featured acts remained buried. Despite their prominence in the video, Aerosmith are not actually credited on Run-DMC’s No. 4 1986 hit “Walk This Way”; and on De La Soul’s 1988 R&B No. 1 “Me, Myself & I,” neither star producer Prince Paul nor special guest Q-Tip from A Tribe Called Quest (who is actually name-checked in the lyrics!) appears on the label. Heck, not even Vincent Price warranted a citation for his rap on Michael Jackson’s 1984 single “Thriller.”

Eventually, though, featured rappers became too prominent to ignore. Arguably, two hits set the template for commercial rap-and-pop crossover before “She Ain’t Worth It” came along. Chaka Khan’s No. 3 1984 smash “I Feel for You” (No. 1 R&B), was a pileup of guests, effectively a four-minute soul-rap revue. Khan’s name is rapped in a sampled loop at the record’s start by frequent Flash collaborator Melle Mel, even before the melody begins; that melody is kicked off by no less than Stevie Wonder on harmonica, and the bridge includes more rapping from Mel plus samples of Wonder’s 1963 No. 1 hit “Fingertips.” (As if all that wasn’t enough, the song was written by Prince.) As per 1984 standards, none of these artists is name-checked in the song’s credits. Were it to be issued today, “I Feel for You” would likely read “Chaka Khan featuring Stevie Wonder and Melle Mel.” (Even Prince might merit a topline credit.)* But regardless of the fine print, “I Feel for You” set an ’80s standard for showcasing featured performers and got the general public comfortable with hip-hop hybridity. The other standard-setter for pop-rap crossover actually did include a featured credit: the 1989 Top 10 hit “Friends,” by Jody Watley with Eric B. and Rakim. This solid slice of danceable R&B by the former Shalamar singer was made immortal by two long rap stretches by Rakim, widely regarded as the late ’80s king of flow. Even more than on “I Feel for You,” the way the rap segments are showcased on “Friends”—Watley producer André Cymone practically clears space in the mix for Rakim to spit and Eric B. to scratch—set a template and presaged what countless ’90s and ’00s hip-pop joints would sound like.

Featured credits didn’t exactly become commonplace after “She Ain’t Worth It,” but as rap was finally embraced at the center of pop, such credits became less remarkable. Moralist bogeyman and 2 Live Crew leader Luther Campbell scored a Top 20 hit, the Springsteen-sampling “Banned in the U.S.A.,” under the nom de rap Luke featuring the 2 Live Crew. Neo-folkie Suzanne Vega was remixed by a British DJ duo calling themselves DNA and had a pop-house hit with “Tom’s Diner,” credited to DNA featuring Suzanne Vega. Before 1990 was over, the hip-house jam “Gonna Make You Sweat (Everybody Dance Now)” by C&C Music Factory featuring Freedom Williams hit the Hot 100, eventually reaching No. 1 in February 1991. Rapper Williams got the featured-credit treatment, but “Sweat” made headlines by failing to credit its singer Martha Wash due to her non–model-thin looks. However, Wash would be effectively avenged less than a year later, by another club banger that set a couple of new standards of its own.

Most of us now think of “Marky” Mark Wahlberg’s 1991 pop-rap hit “Good Vibrations” as the thing he did before modeling underwear, acting in movies, producing bro-y TV shows, and talking to animals. But the song has a legacy, thanks to its full artist credit: Marky Mark and the Funky Bunch featuring Loleatta Holloway. The explosive voice you hear on the song’s chorus belongs to the gospel-trained Holloway, in a sample from her 1980 club smash “Love Sensation”—a song that had also been featured in uncredited samples on hits by Black Box and Samantha Fox. After getting the Martha Wash–style brushoff on those earlier tracks, Holloway successfully pressured Wahlberg’s label to give her featured credit on “Vibrations.” In essence, Wash and Holloway were setting the ’90s template for the female hook singer—the inverse of the featured-rapper model à la Rakim and Bobby Brown. When “Good Vibrations” topped the Hot 100 in October 1991, Holloway became not only the first act given full artist credit for a sample on a No. 1 hit but also the first chart-topping hook singer (a crown that would have already gone to Wash if C&C Music Factory had done right by her).

By the end of ’91, then, the two main models of featured-artist crossover on a big radio hit had been set: the featured bridge rapper, à la “She Ain’t Worth It,” and the featured hook singer, à la “Good Vibrations.” Each is a recipe for melodic, tempo, and genre crossover. The former model takes a fluffy pop song and adds a frisson of hip-hop edge; the latter takes a tart rap joint and leavens it with pop sweetness.

You can break down much of the next two decades of Hot 100 hits through this prism. Some ’90s and ’00s hits adhering to the featured–bridge-rapper model include Michael Jackson’s “Jam” featuring Heavy D; Blackstreet’s “No Diggity” featuring Dr. Dre and Queen Pen; Janet Jackson’s “Got til It’s Gone” featuring Q-Tip; Jennifer Lopez’s “I’m Real (Remix)” featuring Ja Rule; Beyoncé’s “Crazy in Love” featuring Jay-Z; and Rihanna’s “Umbrella” featuring Jay-Z (again). On the featured–hook-singer side, you have Salt-n-Pepa’s “Whatta Man” featuring En Vogue; Warren G’s “Regulate” featuring Nate Dogg; Coolio’s “Gangsta’s Paradise” featuring L.V.; Ja Rule’s “Always on Time” featuring Ashanti; and Nelly’s “Dilemma” featuring Kelly Rowland.

What has made the last 15 years on the chart so remarkable, however, is how many new permutations of cross-genre lead-and-featured artist have scored with the public—and how expansive the industry has become over what qualifies for credit. The liberalization of credits started by rappers has even spread across genres. In his second-wave, turn-of-the-millennium career, guitarist Carlos Santana took lead credit on a string of Top 10 hits while superstar singers including Rob Thomas, Michelle Branch, and Nickelback’s Chad Kroeger received the featured credits. On the mournful soul ballad “I Don’t Wanna Know” by Mario Winans, a No. 2 hit in 2004, the full artist credit included not just rapper P. Diddy but also blockbuster new age warbler Enya; she didn’t sing a note, but a sample of her “Story of Boadicea” formed the backbone of the track and qualified her for a feature (a remarkable inversion of the Loleatta Holloway featured-sample regime). On Kanye West’s 2005 No. 1 smash “Gold Digger,” actor-singer Jamie Foxx, coming off his Oscar-winning turn in Ray, received featured-artist credit for an imitation of Ray Charles that leads off the single and lasts less than 15 seconds; the rest of West’s hit rides atop a sample of the original Charles single “I Gotta Woman.” (West has been known to dole out featured credits to acts like Bon Iver whose contributions are almost undetectable.) In short, the featured-artist credit has become a little bit like the Best Supporting Actor or Actress Oscar: Sometimes the winner really had something closer to a leading role, and sometimes the part is not much more than a drive-by.

Halfway through the 2010s, the charts are awash in featured credits. Four-artist or even five-artist credits (between leads and features) are not unheard of on event singles. The rise of electronic dance music has also inverted the concept of the lead artist: French DJ David Guetta takes lead on virtually all of his tracks despite being supported by very starry singers and rappers, and of course Guetta’s fellow Frenchmen Daft Punk took the lead credit on their blockbuster “Get Lucky,” while their two veteran accompanists, Pharrell and Nile Rodgers, took featured roles. Bruno Mars launched his singing career in 2010 via a featured credit on “Nothin’ on You”—a song nominally led by a rapper, B.o.B, whom Mars has long since eclipsed. This year, Justin Bieber is resuscitating his career by accepting a featured role on “Where Are Ü Now,” a single led by superstar-DJ duo Skrillex and Diplo.

It’s funny when you consider that all this started, however inadvertently, with “She Ain’t Worth It”—a wafer-thin single by a boy-pop crooner looking to up his cred and a New Jack baller looking to expand his dominion. But then, that’s what the featured credit has always been about: mutual advantage. However self-contained some bands might be (or claim to be), pop music, even in the so-called Rock Era, has long been a fundamentally collaborative art form. Hip-hop and electronic music have only brought this collaborative nature out in the open. This summer, when you turn up your radio for Mark Ronson’s “Uptown Funk!” featuring Bruno Mars, Wiz Khalifa’s “See You Again” featuring Charlie Puth, or Taylor Swift’s “Bad Blood” featuring Kendrick Lamar, you’re experiencing the result of decades of music science—our most refined strains of genetically hybridized pop, clearly and unambiguously labeled.

**Here are those couple of asterisks: There are actually two No. 1 hits prior to “She Ain’t Worth It” that had some kind of “featuring” credit, but they’re odd cases that don’t really fit the mold. The 1974 No. 1 instrumental hit “T.S.O.P. (The Sound of Philadelphia)” by the Philadelphia studio collective MFSB features brief vocals by R&B trio The Three Degrees; some single labels formally credited the girl group, but on Billboard’s charts only MFSB were listed. In late 1984, the single “Careless Whisper” was issued in the U.S., Canada, and Japan with the credit “Wham! featuring George Michael”—but Michael was a member of Wham. In England and most other countries around the world, “Careless” was a George Michael solo single; Columbia Records used the odd “featuring” credit only in countries like America where Wham was a new act, one that had just broken weeks earlier with “Wake Me Up Before You Go-Go.”

*Correction, July 31, 2015: This article originally misstated the nature of Grandmaster Flash’s sampled contribution to Chaka Khan’s “I Feel for You.” Grandmaster Flash did not appear on the track.

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