Nineteen Great Songs Made By Teenage Rappers in the Last 19 Years

Is age really nothing but a number?

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Complex Original

Image via Complex Original

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Hip-hop has always been a youthful genre: From the earliest days of parties in Bronx parks to the current era of YouTube videos and Tumblr posts, teenagers have been the ones driving the genre forward.

With their healthy disregard for tradition, brash confidence and wide-eyed excitement, teenagers tend to be at the forefront of the culture, often sparking its most exciting—and often most controversial—trends. Not only are they the ones consuming the culture, teenagers are often the ones making it.

Over the years, teen performers have been responsible for some of rap's biggest hits—almost every major rapper in the '80s, from Run DMC to Rakim, released their first songs as teenagers—as well as some of its greatest controversies. In some cases, age was a convenient marketing gimmick, in others it was merely incidental to a blossoming talent. Some former teenage sensations are now among the most well-loved names in rap, while others stopped making music before the age of 20.

There's always going to be a fair amount of hand-wringing about The Teens and the way they ruin everything, but, as these standout performances show, they've been all right all along.

Written by Kyle Kramer (@kylekramer)

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OutKast "Player's Ball" (1994)

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Label: LaFace/Arista
Producer: Organized Noize
Birthdate: André 3000 - May 27, 1975, Big Boi - Feb. 1, 1975
Age: André 3000 - 18, Big Boi - 18

Even as teenagers fresh out of high school, Dre (this was pre-3000) and Big Boi were making music that sounded timeless, kicking complex flows their peers wouldn't catch up to until the late '90s over warm funk melodies that could have been straight out of the '70s. Originally intended as a Christmas song, "Player's Ball" was adjusted to feature a less seasonally-specific hook (although plenty of holiday references still remained in the lyrics), helping it climb to No. 1 on the Billboard rap charts for six consecutive weeks. A resounding career-launching move—it featured the production of Organized Noize, who would also go on to make classics with Goodie Mob and TLC —the single helped announce the arrival of the South as a progressive part of the hip-hop world.

Shyheim "On and On" (1994)

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Ahmad "Back In the Day" (1994)

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Label: Giant/Reprise/Warner Bros. Records
Producer: Ahmad, Redfoo
Birthdate: 10/12/1975
Age: 19

Even according to the young, youth is wasted on the young. There may be no group as jaded or as nostalgic for the innocence of childhood as teenagers, who are both eager to prove they're real adults and starting to realize that a lot of parts of adulthood suck. Ahmad's "Back in the Day" is the gospel for this group, the words of an 19-year-old sharing the wisdom of old age and wishing his only responsibility was still finishing his homework. The blueprint for many songs by nostalgic teenagers since, "Back in the Day" perfectly captures the wistful vibe of the rearview look with its warm chorus and deeply descriptive verses. As a result, ever since back in the day, the song's been a classic.

Foxy Brown on "I Shot Ya (Remix)" (1995)

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Label: Def Jam
Producer: The Trackmasters
Birthdate: 9/6/1979
Age: 16

When "I Shot Ya" producers The Trackmasters saw Foxy Brown perform at a Park Slope talent show, they were so impressed they recruited her to rap alongside proven heavyweights Keith Murray, Fat Joe and Prodigy on the remix. If anyone was worried that a teenage girl might not have the ferocity to match her collaborators' hardcore lyrics, those fears were quickly dispelled by one of the most swaggering, shit-talking debuts of all time, filled with head-turning lines like "Bitches grab ya tetas, get them n****s for they cheddar/Fuck it, Gucci sweaters and Armani leathers." With such overt confidence and natural flow, Brown quickly became a hot commodity, guesting on high-profile songs with Jay-Z, Toni Braxton and others before even releasing her platinum debut album at the age of 17.

B.G. "Bling Bling" (1999)

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Label: Cash Money/Universal
Producer: Mannie Fresh
Birthdate: 9/3/1980
Age: 18

As far as rap success goes, if the first step is having a video that involves bowls full of money and stretch Hummers and the second is owning a private jet, then the third is coming up with a phrase so good it becomes part of the soccer mom lexicon. By all three counts, Cash Money succeeded with "Bling Bling," a posse cut from B.G.'s Chopper City in the Ghetto. Not only was B.G. still a teenager on the song, the track was the biggest spotlight to date for the 17-year-old Lil Wayne, whose hook and verse hint at his future pop appeal and lyrical dominance, respectively. Even Baby, who's not technically a teenager (he's 30 here), manages to steer clear of adulthood, pointing out that "the Cash Money motto is to drink 'til you throw up." Featuring carefree money boasts over a spry Mannie Fresh beat, the song still sounds relevant today in the Young Money era, proving the staying power of both diamonds and youth.

Lil Wayne "Tha Block Is Hot" (1999)

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Label: Cash Money/Universal
Producer: Mannie Fresh
Birthdate: 9/27/1982
Age: 16 
Perhaps because he's always had an ear for simple, catchy pop hooks, perhaps because he rapped with a distinctive New Orleans accent, perhaps because he started out as just a child, it would take a decade for Lil Wayne to earn acceptance as a great rapper. But even by the time of his solo debut Wayne was spitting complex internal rhymes, switching up flows and displaying an eye for detail to great effect in his verses, particularly on a line like "Pile up in the Eddie Bauer and blocka at every hour." Paired with a highly quotable call-and-response hook from Juvenile and B.G. and a characteristically spry Mannie Fresh beat, the song was a fitting breakout display for the artist who would become one of rap's biggest stars. Even hundreds of freestyles later, Wayne's account of neighborhood crime remains one of his best descriptive moments.

Lil Boosie "For My Thugz" (2002)

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Bow Wow f/ Birdman "Let's Get Down" (2003)

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Label: So So Def/Columbia
Producer: Jazze Pha
Birthdate: 3/9/1987
Age: 16

Lil' Bow Wow may have seemed like an easy target—a child rapper who made an album called Doggy Bag? Of course there was criticism!—but the little dude had more to boast about than a lot of artists twice his age, even if it mostly was due to the work of producer and mentor Jermaine Dupri. Not only did he have girls trying to get at him, he was boasting of his prowess with the ladies in a PG tone and a teen's voice, which makes a line like “I'll find me another one, more interesting more fun/The man has just begun” even colder. With a T.I.-esque flow, paired with a killer, clattering faux-Neptunes beat courtesy Jazze Pha, the kid, the self-proclaimed “Mr. 106 and Park,” was unstoppable.

J-Kwon "Tipsy" (2004)

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Label: So So Def/Arista
Producer: Trackboyz
Birthdate: 3/28/1986
Age: 17

In the midst of this song's thundering drums, crisply delivered background whispers and riotous hook, the anti-teen-drinking PSA at the beginning could easily get lost on an inebriated dancefloor. But the fact is, while this might have been a radio-crushing single perfect for yelling the lyrics to in any context (if you never mumbled "here comes the five to the four to the three" while doing your math homework, you ain't about that life), it's, above all, an ode to the fact that J-Kwon had a fake ID. A really good one, presumably, if he made this song and was still getting away with using it.

The Pack "Vans" (2006)

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Label: Up All Night/Jive
Producer: Too $hort (exec.), Young L
Birthdate: Lil B - Aug. 17, 1989, Stunnaman - Sept. 30, 1987, Lil Uno - July 19, 1990, Young L - Unknown
Age: Lil B - 17, Stunnaman - 19, Lil Uno - 16, Young L - unknown

In the days before The Based God's sneakers became full-on holy relics, Lil B and his fellow members of The Pack—Young L, Lil Uno and Stunnaman—were just really big fans of Vans. Swearing off the relatively expensive name brands like Nike, the group's ode to skate shoes caught the ears of Too $hort, who signed them and oversaw the single's wider release. With a minimalist Bay Area beat from Young L and the synthetic, repetitive hook of "got my Vans on but they look like sneakers," the song was a sleeper hit that hinted at the offbeat brilliance yet to come from the group's individual members.

Huey f/ Bow Wow "Pop, Lock & Drop It (Remix)" (2007)

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Label: Jive
Producer: Calvin Miller Productions
Birthdate: 1/1/1989
Age: 18

Huey's album may have been called "Notebook Paper"—part of a proud tradition of teenage rappers with school-themed releases—but his breakout hit offered instructions so straightforward they didn't need to be written down. Unmistakeably a product of the wave of St. Louis pop rap smashes that ruled radio in the mid-'00s due to Huey's slurred Rs, the so-obvious-it's-brilliant hook and the stomping beat (also Bow Wow's Chingy reference on the remix), "Pop Lock and Drop It" transcended being a momentary dance trend by providing the perfect phrasing for yuppies in their thirties trying to explain the art of hip-hop dance. Perhaps recognizing that he would never again have as big a song (few artists do), Huey also stepped up to the plate to deliver a new, improved verse on the remix, which included a standout T-Pain appearance.

Lil Mama "Lip Gloss" (2007)

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Label: Jive
Producer: James "Groove" Chambers
Birthdate: 10/4/1989
Age: 17

Unlike in the real world, where tremendous wealth or power conveys social status, school hallways have more unpredictable, down-to-earth signifiers: a cool pair of shoes, the ability to grow a beard or, in Lil' Mama's case, a really on-point lip gloss game. Over a stomping beat made for outsized shit talk (it samples one of the original shit-talking teen performances, "Roxanne's Revenge"), Lil' Mama goes in on her skill in applying lip gloss, the variety of flavors at her disposal and the envy she inspires. Drake may brag about older rappers asking him for help, but Lil' Mama had the motherfuckering principal seeking her out for advice. An unexpected pop hit—the song peaked at No. 10 on the Hot 100—"Lip Gloss" made makeup sound like the coolest thing out. There's still a wide open lane for a smash hit about gel pens, though.

Soulja Boy Tell 'Em "Turn My Swag On" (2008)

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Label: Collipark/Interscope
Producer: Natural Disaster, Top Cat
Birthdate: 7/28/1990
Age: 18

While his "ringtone rap" has long made him the poster boy for everything wrong with teenage rappers, Soulja Boy's canny use of social media, disregard for doing what's expected and careful eye for emerging trends have also made him an example of why The Youth are so great. Years ahead of its time, the titanic "Turn My Swag On" is not only the critical link between the opulence of peak T.I.- and Young Jeezy-era Atlanta rap and Waka Flocka Flame's high-decibel simplicity, it's a de facto anthem for getting ready for just about anything. Having trouble waking up, paying attention at work or getting excited to go to your cousin's wedding? You may want to check to see if your swag has been turned off during the dull, anti-swag grind of your post-teenage years. If it has, have you considered what the Deandre Way can do for you?

Lil B "We Can Go Down" (2009)

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Earl Sweatshirt "Earl" (2010)

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Mac Miller "Donald Trump" (2011)

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Label: Rostrum
Producer: SAP
Birthdate: 1/19/1992
Age: 19

The track that catapulted Mac Miller from Pittsburgh's Other Rapper and Occasional Guy on Blogs to the type of artist capable of putting out a No. 1 album, "Donald Trump" works because it taps into an emotion that any teenager who doesn't already have Donald Trump levels of money feels at some point or another. "Hopefully, I'll be at the top soon/For now I'm at my house on the couch watching cartoons," Miller raps, an inspirational guru for those looking for some Supreme on their way to supreme consciousness. Over producer Sap's beat and the insanely catchy "ba-ba-ba-ba-ba-baaa" Sufjan Stevens sample, the line "We gonna take over the world while these haters getting mad" goes from generic rap platitude to triumphant declaration—especially since the song made Trump himself one of Miller's haters. Pissing off America's most insufferable rich dude is something all 19-year-olds should aspire to do.

Joey Bada$$ "Waves" (2012)

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Label: Cinematic Music Group/Creative Control
Producer: Freddie Joachim
Birthdate: 1/25/1995
Age: 17

Joey Bada$$'s mission statement of a single starts out with a voice saying, "you remember back in the days," before throwing us back to the days when a young rapper might prove himself not by unleashing some hot new dance craze or dumb piece of slang but rather by spitting a series of ferocious boasts, battle-ready put-downs and lines eager to prove their cleverness. Lyrics like "Since then it's been a disaster for you and your favorite rapper/Go ahead ask 'em 'Who is Joey Bad?'/Watch 'em gasp, asthma, damn it's so sad" land like a flurry of punches, showcasing Joey's dense rhymes and flexible flow. Optimistic, a little bit silly and overly precocious, the song encapsulates everything great about teenagers and sets the stage for the young rapper to achieve some of his goals. Like, you know, being in Complex.

Chief Keef "Love Sosa" (2012)

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Label: Glory Boyz Entertainment/Interscope
Producer: Young Chop
Birthdate: 8/15/1995
Age: 17

With his simple, almost anti-lyrical style, mumbled delivery and a rise to fame so fast that many dismissed it as pure hype, Chief Keef had plenty of people hoping that his first single after signing a major label deal would be a flop. Instead, the insanely catchy sing-song hook and monster Young Chop beat set the track up to be Keef's biggest hit yet, reaching No. 56 on the Billboard Hot 100 and laying out a blueprint for his rapid evolution from shouting rapper to left-field pop innovator. Full of simple but fantastic lines like "She gon' clap for Sosa/He gon' clap for Sosa," the song showed Keef's appeal more clearly than ever: he makes the wildly unique look alarmingly easy.

Chance the Rapper "Juke Juke" (2012)

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