The 41st GRAMMY Awards were momentous for Lauryn Hill. Not only did she take home five GRAMMYs — the most of any artist that night — but the rapper/singer also made history.

The then-23-year-old rapper/singer's 1999 win for her groundbreaking debut solo album, The Miseducation Of Lauryn Hill, marked the first ever Album Of The Year victory by a hip-hop artist. 

"This is crazy because this is hip-hop music," Hill said before delivering a hoard of thank yous. Watch Hill's heartfelt acceptance speech below.

The New Jersey native received the award from Whitney Houston, who hails from Hill's hometown of Newark. It was clear Houston was rooting for Hill, as she emphatically pointed to the crowd and screamed out a combination of "yes" and "amen," following Hill's name being called.

Over two decades later, Hill's feat remains remarkable. Outkast's Speakerboxx/The Love Below, which won in 2004, is the only other hip-hop album to win the prestigious category.

Hill took home four additional GRAMMYs that night: Best New Artist, Best R&B Album, Best Female R&B Vocal Performance and Best Rhythm & Blues Song (the latter two were both for her hit "Doo Wap (That Thing)"). Those wins added to her history-making evening, as Hill was the first woman to win five or more awards in a single night.

The eight-time GRAMMY winner took home another Album Of The Year the following year thanks to her feature on Santana's Supernatural ("Do You Like the Way"), a track she produced. Prior to going solo, Hill won two more GRAMMYs as a standout member of the rap trio the Fugees, who won Best Rap Album and Best R&B Performance By A Duo Or Group With Vocal in 1997.

Check back every Friday for new episodes of GRAMMY Rewind.

Remembering Betty Davis: 5 Essential Tracks By The Singer/Songwriter, Fashion Icon & Funk Pioneer

2023 has seen countless tributes to hip-hop, celebrating both its golden anniversary and the staying power of a genre that was vilified, underestimated, and branded a passing fad for decades. Nonetheless, while 50 is a major milestone, many believe hip-hop reached its peak decades ago.  

At the tail end of the golden age of hip-hop, the genre reached a new level of maturity. Twenty-five years ago, hip-hop music demonstrated a wide variety of production styles and a diversity of perspectives. Further proving that 1998 was a high watermark for hip-hop, several important and stylistically distinct albums by Jay-Z, Black Star, A Tribe Called Quest and Outkast were even released on the same day.

This diversity of expression resulted in multiple commercially successful, distinct subgenres and niche audiences. The culture moved beyond the bi-coastal hostility that had culminated in the tragic murders of Tupac and Biggie, and the South asserted itself in a big way. The year’s versatility was demonstrated through the emergence of an underground scene that was critical of mainstream hip-hop’s consumerist mentality, but nonetheless thrived alongside commercially successful albums by both new and established artists.  

Southern Hip-Hop Earns Respect 

By 1998 groups beyond the East and West Coasts had started to gain national visibility — a hallmark of hip-hop's growing maturity. 

While Outkast's Andre 3000 famously declared that  "The South got somethin’ to say" in1995, the group didn't earn widespread respect and recognition until three years later. Released in September 1998, Aquemini, garnered near-universal praise — earning Outkast a notoriously rare five mics in The Source — and is still considered to be one of hip-hop’s greatest albums. 

No other hip-hop group sounded like Outkast, and Southern flavor and slang pervaded the album (see the harmonica breakdown in "Rosa Parks"), but it was also the live instrumentation on tracks like "Liberation" and "SpottieOttieDopaliscious" that made the album so special. 

Fellow ATLiens Goodie MOB, a group in the Dungeon Family collective, also released an album in '98. Like Aquemini, their sophomore effort Still Standing was produced largely by Organized Noize and featured a similar production style. 

Outkast and Goodie MOB collaborated often in the 1990s: Aquemini’s "Liberation" only works because of the deeply soulful vocals of Goodie MOB’s Cee-Lo, and Still Standing’s "Black Ice" features one of Andre 3000’s most poetic and brilliant verses. While speaking to the many struggles of being young, Black and poor in the South, these two groups demonstrated how regional pride could be asserted in a more positive way, instead of spilling over into real-life violence; it was evidence of hip-hop’s maturity.

On the more commercial side, Atlanta rapper/producer Jermaine Dupri — who was already producing and writing songs for major R&B artists like Usher and Mariah Carey — released his debut album, resulting in one of the hits of the summer: the bouncy Jay-Z collaboration "Money Ain’t A Thang." New Orleans was also becoming an important locus of Southern hip-hop by 1998, with Master P’s No Limit Records releasing albums by Master P himself, Silkk the Shocker, C-Murder, Mystikal, and Snoop Dogg. Hits included "Make ‘Em Say Ugh" and "It Ain’t My Fault," both containing Mystikal’s distinctive high-pitched growling; his lightning-fast verse on the first song is truly something to behold. Also from Crescent City, Cash Money Records struck gold with Juvenile’s 400 Degreez and his booty-shaking anthem, "Back That Azz Up."

The Rise of Underground Hip-Hop

1998 was also the year "underground" hip-hop bubbled to the surface as a reaction to the genre’s crossover success. It was defined primarily by a critique of the presumed excessive consumerism of mainstream hip-hop, and a desire to return to the days when DJs, b-boys and graffiti artists were as important as rappers. 

Turntablism was strongly associated with this style, as were cyphers — gatherings where rappers, b-boys and beatboxers would form a circle and engage in freestyle battles. The emergence of underground hip-hop was another sign that the genre was maturing as a whole; artists were no longer as worried about the ghettoization by the music industry and some felt that it had strayed too far from its marginalized roots. 

The most significant underground hip-hop album of 1998 was Mos Def and Talib Kweli are Black Star, created by a young duo of Brooklyn MCs. Interestingly, it was released on the same day in September as Aquemini, as well as two other major albums of the year: Jay-Z’s Vol. 2…Hard Knock Life and A Tribe Called Quest’s The Love Movement — which although not an essential listen in their discography, did produce a hit with "Find A Way." Four major albums released on the same day was a testament to how far hip-hop had come. 

In fact, the Black Star album was an explicit critique of the type of consumerist mentality and sexually explicit/boasting lyrics Jay-Z employed on Hard Knock Life. Songs like "Definition" display Mos Def and Talib Kweli’s exceptional lyrical dexterity and clever references, while  "Hater Players" draws a clear line in the sand between commercial hip-hop and the "real MCs." In the latter, Kweli raps: "We ain't havin’ that, reachin’ past the star status that you grabbin’ at/ My battle raps blast your ass back to your natural habitat."

Mos Def’s adaptation of Slick Rick’s "Children’s Story" is a clever screed about the lack of originality within mainstream hip-hop. "They jacked the beats, money came wit' ease, but son, he couldn't stop, it's like he had a disease. He jacked another and another, Michael Jackson, Stevie Wonder." The song was a not-so-veiled reference to the production technique utilized by Puff Daddy, relying heavily on well-known samples of soul and R&B songs.

Black Star also distinguished itself from much of commercial rap of the time by uplifting, instead of denigrating, women. "Brown Skin Lady" is an ode to Black women throughout the African diaspora, presenting a clear contrast to the frequent use of the b-word on Hard Knock Life, particularly on one of its biggest hits, "Can I Get A…" Nonetheless, like many "conscious" rappers — notably, Common, who makes a guest appearance on this album — Black Star reflects the almost-universal homophobia in hip-hop at the time, particularly in Mos Def’s verse on "Re-Definition." 

Despite Jay-Z’s distrust and demonization of women on Hard Knock Life — his third and most commercially successful record — no one can dispute his tremendous verbal prowess and flow, evident on tracks like "N— What, N— Who." And while he called out "gold diggers" in "Can I Get A…," he invited a female rapper (Amil) onto the song — leveling the playing field a bit. 

Production-wise, Jay-Z’s use of the "Annie" theme for the title song was one of the most inspired choices in the genre’s history. The slick production of the album guaranteed it would be a home run; in retrospect, it heralded the future of commercial hip-hop’s sound.  

Oher underground hip-hop artists were making big waves in 1998. Rawkus Records — which released the Black Star album — put out an important compilation, Lyricist Lounge, Volume 1, which featured performances by Mos Def, Talib Kweli, A Tribe Called Quest’s Q-Tip, and the L.A.-based Jurassic 5, who also released their debut album that year. Other West Coast underground artists who released debut albums in 1998 included the Bay Area-based Hieroglyphics and Rasco, and the L.A.-based Aceyalone and People Under the Stairs. 

Debuts, Veterans And The Biggest Album Of The Year 

1998 also saw the release of important debut albums by commercial hip-hop artists like DMX, Big Pun and Black Eyed Peas. Big Pun’s "Still Not A Player" was one of the biggest hits of the year, with his lyricism reminiscent of Biggie. 

DMX had a particularly productive year, releasing two albums in 1998, It’s Dark and Hell Is Hot and Flesh of My Flesh, Blood of My Blood. That year, it was impossible to escape the melodic hook and chorus of "Ruff Ryders’ Anthem" ("Stop! Drop! Shut ‘em down, open up shop") from the first DMX album. DMX also contributed a memorable verse on the Lox’s hit "Money, Power, Respect," off the group’s debut album, released by Puffy’s Bad Boy. 

Beyond the debut albums of 1998, a slew of established artists from various regions and representing myriad styles put out their third, fourth or fifth albums. East Coast artists with new albums included Beastie Boys, Method Man, Redman, Busta Rhymes, Queen Latifah, Gang Starr, Mc Lyte, and Public Enemy, who released a soundtrack album for Spike Lee’s He Got Game. On the West Coast, there were new albums by Cypress Hill, Ice Cube, and Digital Underground. 

Notwithstanding the success of so many diverse hip-hop artists, no album achieved greater heights than Lauryn Hill’s masterful solo debut, The Miseducation of Lauryn Hill. To start, it won Album Of The Year at the 1999 GRAMMYs, a feat never before accomplished for a hip-hop artist, as well as four other golden gramophones. Hill wrote, arranged and produced the album herself, reportedly turning down offers for production help from both her former Fugees bandmate Wyclef Jean and her label, which suggested bringing in Wu-Tang Clan’s mastermind, RZA.

The album was somewhere between R&B and hip-hop (and in fact was nominated and won in R&B instead of rap categories), and right off the bat, the album showcases Hill’s considerable skill as both a rapper and singer. The dancehall-inflected "Lost Ones" takes on an aggressive stance, with Hill rapping in Jamaican patois and invoking phrases of religious retribution, but it’s followed by a neo-soul breakup ballad, "Ex-Factor," featuring Hill’s signature throaty vocals.

The other major hits on the album besides "Ex-Factor" were "Doo Wop (That Thing)" and "Everything Is Everything," which cemented Hill as one of the best lyricists in hip-hop. Twenty-five years later, the whole album holds up beautifully and features some incredible invited guests.

Perhaps it’s not a coincidence that the first hip-hop album to break the Album Of The Year barrier was released in 1998 — when the genre had reached what is arguably its creative apex. With the incredible stylistic and regional diversity of that year’s albums, hip-hop had succeeded beyond its founders’ wildest dreams. 

Hip-Hop Just Rang In 50 Years As A Genre. What Will Its Next 50 Years Look Like?

Last year, pop diva Christina Aguilera returned to her Ecuadorian roots with Aguilera, her first full Spanish-language album since Mi Reflejo (2000). By the end of the year, she snagged multiple awards for the LP, including Best Traditional Pop Vocal Album at the 2022 Latin GRAMMY Awards.

In this episode of GRAMMY Rewind, revisit the moment Aguilera took the stage to accept her gramophone for her self-titled project.

"This is so important to me, and it's been amazing to come back to this home," Aguilera shared before expressing gratitude to her collaborators and longtime supporters.

"The fans, the Fighters, thank you so much!" She squealed. "We've been on this journey for so long, so I couldn't thank you more."

It was quite an eventful night for Aguilera. She received seven nominations in total — including Album Of The Year and Record and Song Of The Year for "Pa Mis Muchachas" — and delivered a show-stopping performance of "Cuando Me Dé la Gana" with Christian Nodal.

Press play on the video above to watch Christina Aguilera's complete acceptance speech for Best Traditional Pop Vocal Album at the 2022 Latin GRAMMYs, and check back to GRAMMY.com for more new episodes of GRAMMY Rewind.

10 Incredible Moments From The 2023 Latin GRAMMYs: Rosalía, Shakira, Peso Pluma & More

After nearly 50 years in the industry, legendary Mexican musician and producer Marco Antonio Solís has established himself as one of the most iconic Latin artists in history – from spearheading one of the bestselling grupero bands, Los Bukis, to creating his own roster of solo hits.

As Manuel Abud, the CEO of the Latin Recording Academy, said of Solís in April 2022, "He continues to break down generational barriers through his poignant lyrics … and inspire greater acceptance and understanding." And seven months later, the icon was honored with the Person Of The Year award at the 2022 Latin GRAMMYs.

"My heart is filled with gratitude," Solís said in Spanish during his acceptance speech. "Gratitude is the heart's memory. I am grateful to everyone who is watching us out there on the television. To all those who have supported me in my career over so many years."

Before leaving the stage, Solís gave an uplifting message to aspiring musicians: "To all those who are dreaming of being here some day, a big hug and never lose courage, and above all, faith in our most loved Creator. You will be here some day. Thank you."

The 2023 Latin GRAMMYs will be held Thursday, Nov. 16, at the Conference and Exhibition Centre (FIBES) in Sevilla, Spain, the first-ever international show in Latin GRAMMY history. Tune in on Univision at 8 p.m. ET/PT (7 p.m. CT).

Press play on the video above to hear Marco Antonio Solís's complete acceptance speech for Person Of The Year at the 2022 Latin GRAMMYs, and check back to GRAMMY.com for more new episodes of GRAMMY Rewind.

2023 Latin GRAMMYs: See The Complete Nominations List