In 2020, rapping is singing and vice versa, but it obviously wasn't always that way. Throughout rap history, artists have flirted with the idea of trading gruff, aggressive vocals for melody, but the transition was usually gradual.

Back in 1989, Biz Markie unleashed some hilariously amateur vocals on his song "Just a Friend." While you might think that was his first time singing on wax, he'd actually indulged in some melody on a song from his Goin' Off album, which was released the year before. Drake, who became a near-instant superstar with the release of his breakout single "Best I Ever Had" in 2009, had actually made a complete dive into R&B at least one year before the release of that particular song.

Future and Young Thug, two other rap vocalists that helped remix the rap genre as a whole with their singing in Auto-Tune styles, didn't start out their career using Auto-Tune. As a member of Organized Noize sometime during the early-to-mid 2000s, Hendrix, who was rapping under the name Meathead at the time, was doing some straightforward rapping. He wouldn't dive into the world of singing until he dropped his debut mixtape, 1000, in 2010. By the time he dropped his Hndrxx album in 2017, he was all in with the melody.

For his part, Thugger was delivering Lil Wayne-esque raps throughout most of his first mixtape, I Came From Nothing, but at one point on the 2011 project, he does some warbling that served as a precursor to the elastic, extraterrestrial vocals he'd flaunt on subsequent projects like Slime & B, his newly released joint mixtape with Chris Brown.

Whether it's an A-List superstar experimenting as they sing their own hook or a rising star releasing their first Auto-Tune-heavy single, everyone starts somewhere. Today, XXL takes a look back at artists singing on their own songs for the first time. Peep the list below.

  • Lauryn Hill

    "His Eye Is on the Sparrow"

    Lauryn Hill had teamed up with Wyclef Jean and Pras years earlier, but the Sister Act 2: Back in the Habit soundtrack song "His Eye Is on the Sparrow" in 1993 marked the first time she could be heard singing on a song of her own. The track is performed by Hill and Tanya Blount, both of whom acted in the Whoopie Goldberg-starring film.

  • Kanye West

    "Heavyhitters" Featuring GLC

    Before Kanye West went full Auto-Tune on his 808s & Heartbreak album or even before he crooned on The College Dropout tracks "We Don't Care" and "Spaceship," Kanye West dipped his toes in the singing waters on "Heavyhitters." The GLC-featured song belongs to his 2003 mixtape, I'm Good. He doesn't go all in here, but he carries enough for this one to qualify as his first on-record singing performance on a solo record.

  • Ja Rule

    "The March Prelude"

    The first time Ja Rule sang on a record of his own was for the first song on his 1999 debut album, Venni Vetti Vecci. On "The March Prelude," Ja lets out a drowsy thug's prayer to set off his debut LP. This was just a prelude to the sultry duets he'd drop in subsequent years ("Put It on Me (Remix)" with Lil Mo, "Mesmerized" with Ashanti), but it's clear Murder Inc. liked what they heard here.

  • Pharrell


    Although Pharrell had sung small parts on songs dating back to 1993 (SWV's "Right Here (Human Nature Radio Mix)"), he didn't belt out any notes on a song belonging to himself or his group N.E.R.D until May 2001. That's when he laced the group's song "Lapdance" with his falsetto.

  • Biz Markie

    "This Is Something for the Radio"

    Biz Markie is most known for belting his heart out on his 1989 single "Just a Friend," but he first did some singing a year earlier. On his 1988 song, "This Is Something for the Radio," which belongs to his 1988 album, Goin Off, Biz provides some casual harmonies for the hook.

  • Missy Elliott

    "First Move"

    Before she unloaded her debut album, Supa Dupa Fly, in 1997, Missy Elliott was part of an R&B group called Fayze. In 1991, the group released the song "First Move," on which Missy sings.

  • Nicki Minaj

    "Kill Da DJ"

    Nicki Minaj showcased her pipes for the first time on her Beam Me Up Scotty mixtape cut "Kill Da DJ." The project was released on April 18, 2009.

  • Drake

    "Brand New"

    Drake's first foray into singing came on "Brand New," a track that leaked onto the internet in early 2008. The song eventually landed on his breakout 2009 mixtape, So Far Gone.

  • Trippie Redd

    "Dirty Redd"

    Coming of age during the advent of genre-fluid, Auto-Tune-heavy SoundCloud rap, its no surprise that Trippie Redd was melodically inclined from the jump. The first song Trippie Redd uploaded to his SoundCloud account was "Dirty Redd," and on it, he sings some flexes.

  • PnB Rock


    On the intro song for his 2014 mixtape, Real Nigga Bangaz, PnB Rock does some singing as he spits about his life of hardships.

  • Future

    "Life of a G"

    After operating as an Organized Noize member who rapped under the name of Meathead, the rapper re-emerged as Future with his debut solo mixtape, 1000. On "Life of a G," which is the first full song on the project, he sings parts of the hook.

  • XXXTentacion

    "Vice City"

    XXXTentacion sings the opening few seconds on the very first song he ever uploaded to SoundCloud. It's called "Vice City," and he dropped it back in 2013.

  • Skooly


    Skooly first tried his hand at singing on the lead single for Money Swag, a 2009 release from his group Rich Kidz. The song is called "Wassup," and it finds Skooly, then known as Skoolboi, delivering a simple melodic hook that immediately gets stuck in your head,

  • Tory Lanez

    "T Dot Girls"

    On "T Dot Girls," Tory Lanez made known his knack for singing all the way back on his first mixtape 11 years ago. For the track, which belongs to 2009's T.L 2 T.O, Lanez half-sings a hook paying homage to girls from Toronto.

  • Kid Cudi

    "Day 'n' Nite"

    Kid Cudi's debut single, "Day 'n' Nite," established him as a leader at the forefront of rap's venture to the melodic side of music. For the song, which dropped back in February of 2008, Cudi sings about depression and the use of drugs to help deal with it.

  • Fetty Wap

    "Make It"

    Before Fetty Wap struck gold with "Trap Queen" in April of 2014, he debuted some of his singing vocals on "Make It," a track he'd released a couple of months prior to dropping his breakout single.

  • Post Malone

    "That's It"

    Having been raised on the sounds of rock and hip-hop, Post Malone's rap style was always destined to incorporate lots of singing. For "That's It," which is a song Posty uploaded to his SoundCloud account in January of 2015, he sings in a way that reflects his style to this day.

  • Young Thug

    "Ball on Y'all"

    Young Thug jumped into some slight singing on his 2011 debut mixtape, I Came From Nothing. You can hear Thugger sing on the song "Ball on Y'all." It's not the eccentric, hyper-animated stuff that would come just two years later, but it's an early sign that Thugger was never going to just do one thing.

  • Gunna

    "Hard Body"

    Before he was Gunna, Sergio Kitchens rapped under the slightly different name Yung Gunna, and he dropped a mixtape called Hard Body in July of 2013. The titular song is the first Gunna track you can hear him sing on.

  • Ski Mask The Slump God

    "Intro (I Don't Care)"

    Back in July of 2016, Ski Mask The Slump God gave the whole singing thing a try on his Slaps for My Drop-Top Minivan cut, "Intro (I Don't Care)." For the song, Ski uses some Auto-Tune and sings over a beat that features a sample of Vanessa Carlton's "A Thousand Miles."

  • Childish Gambino


    The earliest available recording of Childish Gambino singing comes on his Poindexter cut "Extraordinary." For the song, he croaks some lyrics that interpolate Jay-Z's American Gangster cut "Say Hello."

  • Rich Homie Quan

    "I Go in on Every Song"

    Rich Homie Quan was out here singing from the jump. On the hook for the title track of his I Go in on Every Song mixtape, which was released on April 1, 2012, Quan sings the hook. He flaunts his sing-song rap flow throughout the entire project.

  • K Camp

    "You Know"

    K Camp showcased his melodic side for the first time on his own song "You Know." The track belongs to his first official mixtape, Become a Fan, which was released on April 28, 2011.

  • Snoop Dogg

    "Pay for Pussy"

    Snoop Dogg tried his hand at singing for the first time on a short, interlude-ish song called "Pay for Pussy." The song belongs to his debut No Limit Records album, Da Game Is to Be Sold Not Told.

  • André 3000

    André 3000 jumped into singing waters for the first time on wax all the way back in 1996. That's when he joined his OutKast groupmate Big Boi to sing the eerie hook for "Elevators (Me and You)." The song came out when OutKast's ATLiens album was released on Aug. 27, 1996.

  • Lil Uzi Vert


    Lil Uzi Vert's first official foray into melody unfolded on his 2014 song, "Understand." The Metro Boomin-produced track was released on The Real Uzi, which dropped back on Aug. 5, 2014.

  • ILoveMakonnen

    "The Newness"

    In August of 2010, four years before he released his breakout single, "Tuesday," ILoveMakonnen used his Myspace page to drop "The Newness," which appears to be the very first song he ever posted online. He sings for a portion of the hook.

  • CeeLo Green

    CeeLo Green's got a sing-song verse on Goodie Mobb's debut single, "Cell Therapy," and his vocals can be heard on the hook, too. The song was released in 1995.

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