If hip-hop is a monument to American imagination and expression, you can trace it story by story. Since its inception in 1973, the genre’s development can be traced era by era, region by region and scene by scene.

GRAMMY.com’s published hip-hop essentials lists leading up to the present, but this playlist is the culmination.

To mark hip-hop’s 50th anniversary, press play on the playlist below, or head to Amazon Music, Spotify, Apple Music and Pandora for a crash course in this quintessential stateside artform — further proof of the genius of Black American music.

And for a deeper dive, revisit GRAMMY.com's essential releases by decade, which unpack hip-hop's most impactful albums and tracks from the 1970s, 1980s, 1990s, 2000s, 2010s, and the 2020s thus far.

19 Concerts And Events Celebrating The 50th Anniversary Of Hip-Hop

Coolio was living in the "Gangsta's Paradise" of his own creation when the 1996 GRAMMY Awards rolled around. The year before, the ode to hip-hop culture had not only become a global No. 1 hit for the rapper, but also the best-selling song of 1995 in the U.S. And that February night in Los Angeles' Shrine Auditorium, the track won Coolio his first GRAMMY, for Best Rap Solo Performance.

Receiving the trophy from Salt-N-Pepa and Mary J. Blige (clad in head-to-toe leopard print), the rapper emerged from backstage with his overjoyed entourage in tow, and started out his acceptance speech by claiming his GRAMMY "for the whole hip-hop nation."

"West Coast, East Coast, worldwide — united we stand, divided we fall. Recognize," he continued before going on to thank God, his then-fiancée Josefa Salinas and his kids, as well as Stevie Wonder, Quincy Jones, his collaborator L.V., Michelle Pfeiffer (who starred in the song's music video) and others.

Coolio then ended his remarks on a serious note, acknowledging, "We've had a lil' problem lately in high schools and I only got one ting to say to all my Black and Latino brothers out there fightin': Ain't no gangsters living in paradise." 

During the telecast, Coolio also took to the stage to perform "Gangsta's Paradise," which had earned a second nomination for Record of the Year. (That major award ultimately went to Seal's "Kiss From a Rose," along with Song of the Year.)

Sadly, the gangsta rap pioneer died in September 2022 at age 59 after suffering an accidental overdose laced with fentanyl. Press play on the video above to revisit Coolio's GRAMMYs win and check GRAMMY.com for more new episodes of GRAMMY Rewind.

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Lil Wayne had already hit a new high point when he released "A Milli" in the winter of 2008. "Lollipop," the single that directly preceded "A Milli," had scored the rap legend his first hat trick by hitting No. 1 on the Billboard Hot 100, Hot R&B/Hip-Hop Songs and Hot Rap Songs charts.

With "A Milli," the rapper born Dwayne Carter Jr. continued his chart-topping success by capturing yet another No. 1 on the latter two tallies and winning him the GRAMMY for Best Rap Solo Performance at the 2009 ceremony. The modern classic also heralded Wayne's blockbuster album Tha Carter III, which became the final album of the decade to sell more than a million copies in its opening week.

In this new episode of Hip-Hop Re:Defined, rising rap star Armani White tackles Wayne's noughties smash, with the Philadelphia-born newcomer building his flow over the same stuttering sample of A Tribe Called Quest's "I Left My Wallet in El Segundo" as the original.

"A millionaire/ I'm a West Philly millionaire, tougher than Nigerian hair/ My criteria compared to your career just isn't fair," White raps, personalizing the lyrics with a shout-out to his hometown while still echoing Weezy's trademark cadence.

In May, White dropped his major-label debut, Road to Casablanco, with the EP led by his viral single "BILLIE EILISH" and its official remix featuring Ludacris, Busta Rhymes and N.O.R.E.

Press play on the video above to watch White rip through "A Milli," and check back to GRAMMY.com for more new episodes of Hip-Hop Re:Defined.

K-Pop's Hip-Hop Roots: A History Of Cultural Connection On The Dancefloor

"We done split it down the middle so you can see both the visions," raps Big Boi on "Tomb of the Boom," one of the highlights from Outkast's 2003 magnum opus. And he wasn't kidding.

Essentially two solo albums for the price of one, Speakerboxxx/The Love Below saw Atlanta's premier hip-hop duo take the creative reins for one disc each, resulting in a whopping 135 minutes and 40 tracks of genre-hopping genius.

Favorably compared with classic double albums such as Prince's Sign O' The Times, Pink Floyd's The Wall and the Beatles' The White Album, the follow-up to 2000's Stankonia enjoyed similarly super-sized success, too. It topped the Billboard 200 for seven weeks on its way to worldwide sales of 11.4 million, spawned two No. 1 hits and picked up six nominations at the 2004 GRAMMY Awards — which resulted in three wins, including the coveted Album Of The Year.

And a full 20 years on from its Sept. 23, 2003 release, Outkast's fifth studio effort still stands up as a fearless, funkadelic and forward-thinking body of work. Below, take a look at 10 reasons why Speakerboxxx/The Love Below still has the power to get us all shaking it like a Polaroid picture.

It Helped Outkast Join An Exclusive Chart Club

Only 14 acts in the history of the Billboard Hot 100 have knocked themselves off the top spot. And Outkast joined that illustrious group — which also now includes the likes of Drake and Taylor Swift — in 2004 thanks to two of the era's most addictive hits.

The Little Richard-goes-power pop of "Hey Ya!" was the first to reach the summit, spending nine weeks there between December 2003 and the following February. And then it was finally dislodged by the brassy Southern hip-hop of Sleepy Brown collaboration "The Way You Move," which enjoyed just seven days in pole position before Twista's "Slow Jamz" put an end to the Outkast stranglehold.

It Doubled Outkast's GRAMMY Count

By 2004, Outkast were no stranger to the GRAMMY Awards. They'd picked up Best Rap Performance by a Duo or Group for "Ms. Jackson" and Best Rap Album for Stankonia in 2002, and then emerged victorious in the former category again a year later for "The Whole World." But it was the 2004 ceremony where they truly reigned supreme.

The duo stole the show with two memorable performances. First, Big Boi performed "The Way You Move" in a star-studded Funk Music Tribute, which also included legends George Clinton, Earth Wind and Fire and Robert Randolph. Later, André 3000 closed out the show with a celebratory rendition of Best Urban/Alternative Performance winner "Hey Ya!"

The "Hey Ya!" performance was a fitting end to the night indeed, as the pair took home the final — and most prestigious — award: Speakerboxxx/The Love Below was crowned Album of the Year. (It also won Best Rap Album earlier that evening.)

It Spawned Several Classic Videos

Outkast had always been a visual hip-hop outfit, but their videography undeniably peaked with the Speakerboxxx/The Love Below campaign. "Hey Ya!" deservedly picked up four MTV Video Music Awards thanks to its inspired tribute to the Beatles' debut on "The Ed Sullivan Show" — and André 3000's portrayal of all eight of the fabulously named musicians in the video, including guitarist Johnny Vulture and drummer Dookie Blossom Gain III.

Also directed by Bryan Barber, the "The Way You Move" video saw Big Boi showcase his lyrical flow in everything from a rim shop and old-school music hall to dojo and safari retreat. "Roses," meanwhile, finally allowed both members to share the screen as warring members of rival high school crews in a tongue-in-cheek homage to West Side Story.

It Boasts An Impressively Diverse Guest List

Big Boi roped in several usual suspects on Speakerboxxx, including Big Gipp on "Tomb of the Boom," Killer Mike on "Bust" and Cee-Lo Green on "Reset," while also securing the talents of heavy hitters like Jay-Z, Ludacris and Lil Jon and the East Side Boyz. While an undeniably impressive guest list, André 3000's choice of collaborators was even more intriguing.

Shortly before teaming up with the rapper on her own track "Millionaire," Kelis lent her signature husky tones to the appropriately creepy funk of "Dracula's Wedding." Hot on the heels of Come Away with Me, Norah Jones provided the necessary sultriness on the acoustic "Take Off Your Cool." And perhaps most unexpected of all, Hollywood actress Rosario Dawson proved her diva credentials on the metallic funk of "She Lives In My Lap." The Love Below's roll call was yet another sign that Outkast weren't interested in playing by hip-hop's rules.

It Samples Wisely

Considering Speakerboxxx/The Love Below consists of 40 different tracks and clocks in at nearly 135 minutes, it's surprising that Big Boi and André 3000 only relied on a handful of samples. And like their choice of collaborators, they're far from obvious, either.

Who knew that The Sound of Music showtune "My Favorite Things" would work as a drum and bass instrumental? Or that Timmy Thomas' one-hit wonder "Why Can't We Live Together" and the sensual New Jack Swing of Aaliyah's "Age Ain't Nothing But a Number" would fit perfectly as on "Pink and Blue"?

Elsewhere, the propulsive electronic hip-hop of opener "Ghetto Musick" borrows from Patti LaBelle's '80s soul jam "Love, Need and Want You," while "She Lives in My Lap" lifts from both Geto Boys' "Mind Playing Tricks on Me" and Volume 10's "Pistolgrip-Pump."

It Paved The Way For Genre-Hopping

While genre boundaries have been well and truly broken down in today's streaming era, back in 2003, most major artists stayed in their lane — but not Outkast.

The Love Below certainly has little regard for pigeonholing, veering from big band crooning ("Love Hater") to celestial neo soul ("Prototype") to twitchy electro ("Vibrate") with both confidence and panache. The more-focused Speakerboxxx also keeps listeners on their toes, whether it's with the squelchy P-funk of "Last Call," punchy rap-rock of "Bust" or the mariachi-tinged hip-hop of "The Rooster."

Despite its mammoth running time, the album impressively never repeats itself, providing more flashes of invention than most of the duo's peers manage in an entire career.

Even The Interludes Are Inspired

Of Speakerboxxx/The Love Below's 40 tracks, 11 could be classed as interludes — a number that would normally draw groans, especially considering how much they're often the bane of a hip-hop album. But while the blink-and-you'll-miss-it contribution from comedian Henry Welch ("D-Boi") and the brief helium-voiced reprise of "Bowtie" are rather pointless, the majority of the breathers do add something to the record.

"Interlude" is a hypnotic spoken word piece which offers a crash course in Outkast history ("Believe in the dirty Southernplayalisticadillac-funky-ATLiens/ Together, makes Aquemini"). "The Love Below (Intro)" is a sumptuous orchestral number in which André 3000 throws things back to the Rat Pack. And "God (Interlude)" finds the latter living up to his horndog reputation in a cheeky prayer recited over some sun-dappled guitars.

It's About Both Love And War

As titles such as "Happy Valentine's Day," "Behold a Lady" and, of course, The Love Below would suggest, André 3000's half of the album is largely focused on the affairs of the heart — no doubt informed by his break up from Erykah Badu and subsequent quest to find 'the one.'

But to counterbalance all the love talk, Speakerboxxx is a more socially-conscious record in which Big Boi tackles themes of spirituality, philosophy and politics, none more so than on "War," a fervent protest song which no doubt left George W. Bush's ears burning ("Basically America, you got f—ed/ The media shucked and jived, now we stuck, damn.")

The Pair Deliver Career-Best Vocals

Free from having to battle for space on the same track — they only appear together on "Ghetto Musick," "Knowing" and "Roses" — Big Boi and André 3000 have arguably never sounded better than on their respective discs.

The former is in particularly ebullient form on his alter ego Sir Lucious Left Foot's origin story "Unhappy," and also spars well with hip-hop giants Jay-Z and Ludacris on "Flip Flop Rock" and "Tomb of the Boom," respectively. His regular partner in crime, meanwhile, appears to relish channeling his inner Prince on the falsetto-led "Spread" and final single "Prototype."

It Helped Revive The Hip-Hop Double Album

The mid-'90s had been a boom period for the hip-hop double album, with Tupac Shakur's All Eyez on Me, Notorious B.I.G's Life After Death and Wu Tang Clan's Wu Tang Forever regarded as the holy trinity. But the concept had fallen out of favor until Outkast's Speakerboxxx/The Love Below shifted nearly six million copies in the United States alone.

Following its triumph, Nas (2004's Street's Disciple), UGK Underground Kingz (2007's Outkast-featuring Underground Kingz) and Tech N9ne (2008's Killer) all got in on the act. More recently, Vince Staples (2015's Summertime '06), Drake (2018's Scorpion) and Kendrick Lamar (2022's Mr. Morale & The Big Steppers) have also tried to bottle lightning twice. But while they all have their high points, none quite match up to the sheer brilliance of Outkast's crowning glory.

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Although they might seem like disparate genres today, K-pop and hip-hop go way back. Their link can be traced to a single nightclub in Korea: Moon Night. 

Located in Seoul's Itaewon neighborhood, Moon Night wasn't particularly remarkable among the many other bars catering to tourists and American servicemen at the nearby military base. However, in the late '80s and early '90s, the club was ground zero for the genesis of the nation’s first K-pop group and the founding of the country’s "Big 3" music entertainment labels. 

Moon Night is so crucial to the development of K-pop as we know it today because the club played music beloved by its target clientele: Americans. And in the midst of hip-hop's golden age, hip Korean audiences got hooked.

Over decades, that connection to hip-hop has developed and evolved to create the juggernaut that is contemporary K-pop. Today, the influence of hip-hop can be seen in K-pop dance, dress and even instrumentation.

Pioneering K-Pop On The Dancefloor

Where nightlife in Korea was long separated by nationality — Korean citizens had their own establishments, as did U.S. military personnel — a new kind of integrated club scene blossomed in the 1990s. For the first time, Koreans could legally patronize the same bars as American G.I.s. 

Around 1 a.m., clubs like Moon Night would transition from a "normal Korean club" to a foreigner haven, recalls Dr. Michael Hurt, an Assistant Professor at the University of Suwon's International College.

That Moon Night became the Ur of K-pop as we know it was chiefly because Black American soldiers patronized the club, which played hip-hop. As Koreans and Black soldiers socialized, a new culture of hip-hop dance, or "rap dance," and music grew. Dr. Hurt experienced the eagerness with which young Koreans learned hip-hop moves while visiting Moon Night in the '90s. 

Dr. Hurt — who is Black and Korean and has been living in country for various periods since the mid-'90s — recalls clubgoers asking to dance with him. They would follow along with every step. While hip-hop music was important to the progenitors of K-pop, Koreans at the time were most fascinated by dance moves, and the emphasis on dance remains an important aspect of K-pop today. 

By the early '90s, hip-hop had begun to egress its original audience and evolve into a new form. The cross-cultural connection happening at Moon Night was replicated across Seoul; Dr. Hurt notes that Koreans and Black Americans also found common musical interest at Blue Monkey in Sincheon and Golden Helmet in Hongdae.

Future K-pop heavy hitters like Yang Hyun-suk of YG Entertainment, Park Jin-young of JYP Entertainment, and Lee Soo-man of SM Entertainment were rumored to have patronized Moon Night. However, Dr. Hurt theorizes that if they were in the club scene they also visited other places too.

K-Pop's First Generation Of Stars: Born At Moon Night, Shared Online 

While hip-hop was largely inaccessible to Koreans in the 1990s, there were always dedicated Korean listeners. This young, niche community consisted of members like Seo Taiji, who brought rap dance to the public and became K-pop's first stars. 

Seo Taiji and Boys reportedly learned how to dance from Black American soldiers at Moon Night. (Yang Hyun-suk, who later on became the founder of YGE, and Lee Juno were the "and Boys" component of the trio.) Their example laid the groundwork for the second generation of K-pop stars. 

"[Seo Taiji and Boys] were like gods on earth," recalls Dr. Hurt. 

The members became the undisputed purveyors of hip-hop in Korea, utilizing American hip-hop, metal and punk to create a unique musical fusion. The practice of mixing and melding genres is the standard in K-pop to this day.

Seo Taiji and Boys' 1992 performance of "난 알아요 (I Know)" on a competitive TV show struck a chord with the nation's youth, effectively introducing hip-hop to the general public. The performance also filled a capacious hole left in the Korean music industry after the roll back of Emergency Measure No. 9 (which only allowed patriotic or "healthy" songs to be broadcast), which banned hundreds of songs from the likes of Bob Dylan, Johnny Cash and Eric Clapton. Therein, Seo and company brought a new sound to the previously restricted airwaves. 

Still, a lesser-known idol predates Seo Taiji and Boys' rise by a couple of years. Once again, Moon Night remains in the backdrop.

If Seo Taiji and Boys is K-pop’s first idol group then Hyun Jin-Young is K-pop’s first solo artist. Though his career was brief, Hyun Jin-Young "is generally credited with bringing hip-hop to the mainstream in Korea," says Dr. Crystal Anderson, Associate Director of Engaged Learning and African and African American Studies at George Mason University. On hits like, "슬픈 마네킹 (Sad Mannequin)," Jin-young sang, rapped, and performed dance moves, such as the Roger Rabbit, over a hip-hop beat. "Without him, you wouldn't have [K-pop] idols, but at the same time, Seo Taiji showed that it could be lucrative and popular." 

Artists like Hyun Jin-Young, Seo Taiji, and, later, H.O.T were at the forefront of Korea's "rap dance" scene in the mid-to-late '90s. At the turn of the century, hip-hop culture began to circulate even further via the internet.

"The young hip-hop community [in Korea] has always been pretty hardcore because they had to be to even get enough information to maintain community," Dr. Hurt notes. "[Things] like what are the new fashions, you had to be deep into it."

Youth were largely responsible for disseminating the burgeoning sound of K-pop. "Music ​is ​not ​becoming ​popular ​at ​church. ​It ​starts ​from ​some ​kid ​pirating ​a ​CD," says Kirsten Keels, a 2021 Fulbright Korea scholar.  

Online, Koreans could explore hip-hop even further. In BTS’ book, Beyond The Story, RM recounted learning  about hip-hop through interviews and documentaries about rappers posted on YouTube as a teen. His interest in hip-hop would later cause a ripple effect that would lead him to his current position in BTS.

"Legitimizing" Hip-Hop In K-Pop's Second Generation

By the second generation of K-pop, which roughly begins in 2003, the days of "rap dance" had fizzled out in favor of a distinct K-pop sound. However, hip-hop’s presence in the genre remains in the form of creating a designated rapper in each idol group.

Korean Americans also played a significant role in the "legitimization" of hip-hop and K-pop. "In the early days of K-pop, particularly with the idol groups, you would have one or more members who were Korean American. The idea was they were closer to the source material and therefore it was more authentic," says Dr. Anderson. 

This rings true for K-pop groups like H.O.T — Lee Soo-man of SM Entertainment's first massively successful group —  and 1TYM, which had Korean American members. Both groups have been cited as inspiration for groups like BTS and 2PM. H.O.T's successful formula became the blueprint for many K-pop groups. They industrialized the K-pop system, much as Motown developed its artists and hit-making processes. 

Hip-Hop Artists And K-Pop Idols: Past And Present

Decades after its inception, K-pop and hip-hop acts continue to work together. In 2004, Snoop Dogg and Warren G hopped on Jinusean’s track, "2 All My People." The song's infectiously funky beat made the two rappers' appearance feel seamless.

In 2010, Kanye West was featured on JYJ’s "Ayy Girl" (West also appeared in the music video). And two years later, Psy, who has been a lifelong fan of M.C. Hammer, performed the rapper’s signature dance move next to him at the 2012 American Music Awards.

K-pop and hip-hop royalty came together in 2013 when BIGBANG’s G-Dragon and Missy Elliott gave a mesmerizing performance of "Niliria" on "M-countdown", a weekly music program broadcasted by M-net.  It was a legendary moment in K-pop history because it brought together two highly respected rappers from different countries.

One group in particular has a slew of hip-hop collaborations – BTS. It doesn’t come with much surprise, since the septet’s CEO has openly stated "Black music is the base" of their musical identity. BTS and its members have collaborated with the likes of Nicki Minaj, J.Cole, Wale, Desiigner, Juice WRLD, and Lil Nas X (with whom they performed at the 2020 GRAMMYs). Recently, Jungkook, the youngest member of the group, made his solo debut with the song "Seven" featuring Southern rapper, Latto. The song hit No. 1 on the Billboard Hot 100.

In 2017, Jay-Z signed former 2PM leader Jay Park (who takes his name from the multi-GRAMMY winner) to Roc Nation. The following year, Park was seen at Roc Nation’s annual brunch where he snapped pictures with the likes of Beyoncé and Big Sean. His debut EP, Ask Bout Me, featured rappers such as 2 Chainz, Rich The Kid, and Vic Mensa.

Hip-hop’s influence on K-pop runs through the genre’s past, present and future. K-pop and hip-hop artists have always had moments of mutual respect. Even at the most unsuspecting times, the two genres have always found ways to collaborate. 

Understanding Appropriation

However, the earnestness with which K-pop takes inspiration from hip-hop has understandably been questioned. The topic of cultural appropriation continues to be divisive, and unanimous consensus a rarity. "One person's appropriation isn't necessarily another person's appropriation," says Dr. Anderson. 

Lately, the conversation around cultural appropriation in K-pop is commonly in relation to visual signifiers. Instances where K-pop idols have been in the hot seat include but are not limited to: ATEEZ’s Hongjoong wearing cornrows in promo images, BLACKPINK’s Lisa sporting box braids on multiple occasions, and MAMAMOO’s Hwasa donning a durag. While there's often swift backlash from fans, response from record labels is typically delayed — if they acknowledge the uproars at all.

In 2019 and 2020, respectively, former CLC member Sorn posted a picture of someone dressed in a mask that resembled a racist caricature, while Stray Kids' Hyunjin imitated a Korean cartoon character that was reportedly based on Black racial stereotypes. The latter eventually issued an official apology, while Sorn continued to get into hot water — most recently for a photoshoot where she flaunted an afro. 

These recent cases are just repeat offenses of longstanding practices. In the '90s, JYPE Founder Park Jin-young put backup dancers in blackface and afros. The Bubble Sisters infamously wore blackface for their debut cover art and corresponding promo pictures in 2003. 

BTS' J-Hope raised eyebrows with his remake of Webstar and Young B’s 2006 track "Chicken Noodle Soup." The 2019 track featured Becky G, while J-Hope appeared with a gelled hairstyle that resembled dreadlocks. While the look bordered on appropriation, Young B praised the song in an interview with Billboard. 

"People of all cultures know the song," Young B said."[J-Hope and Becky G] made it even bigger for this day and age. I’m very open-minded and I feel like [the remake] is good for the culture. It was created in Harlem, and now it’s a worldwide thing."

"There’s a legit reason for people to be angry because aspects of African American culture have been and continue to be appropriated… the problem with Black popular culture is [it’s] so damn successful," Dr. Hurt says."[It’s] so hyper-successful that in a way you can't make restraining claims on it. I don't think it's at all realistic anymore." 

Cases of appropriation can get harder to identify when there seems to be no clear signs of foul 

play. RAIN and J.Y. Park’s 2020 duet, "Switch To Me," is redolent of Bobby Brown’s 1988 tune, "Every Little Step." The beat, clothing, and dance moves show that Park Jin-young was inspired by Brown. 

"My baseline for a negative appropriation and misappropriation is a racial performance that mocks or demeans," Dr. Anderson adds. "We need to recognize that there's another perspective, not necessarily to excuse some of the more egregious cases of negative appropriation,. We can't use our American racial lens and just put it over this thing and have it make sense because there are other factors at play."

Sometimes the boundaries are pushed too far and are met with legal contention. In 2004, first-generation K-pop group Baby V.O.X released "Xcstasy," utilizing a freestyle Tupac made while incarcerated. The group’s label founder, Yoon Deung Ryong, vehemently denied the rumors that they illegally used the late rapper’s voice and likeness. However, reports from that time failed to corroborate their label’s defenses. In 2020, "Cupid Shuffle" singer Bryson Bernard accused and threatened to sue K-pop group Seventeen for their song "Left & Right" which sounded comparable to his 2007 hit. 

Over the past three decades, hip-hop has become part of Korea’s public consciousness resulting in the K-pop we see and hear today. The spark that Black American GIs, Seo Taiji, and hip-hop-loving Korean youth lit has exploded into a billion dollar industry. Although it can come at the cost of misappropriation and well-meaning appreciation, it ultimately shows the influence of hip-hop and Black popular music around the world.

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