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.

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For 15 years, The Roots have gathered the music’s brightest and fastest-rising talents to perform in Philadelphia for their annual Roots Picnic, and this year’s lineup was nothing short of star-studded. 

After kicking off the weekend with Dave Chappelle’s comedy show at the Wells Fargo Center on Friday, the action moved to the Mann Center in Fairmont Park where fans witnessed surprise crew reunions, unexpected cameos, and a taste of the Las Vegas strip across three performance stages. 

On Saturday, legendary rap group State Property reunited for the first time in years, Lil Uzi Vert rocked out with the Park Stage crowd for his third picnic appearance. Supported by the Soulquarians, legends the Isley Brothers and Roy Ayers lit up the Park stage. Lauryn Hill closed out day two by commemorating her GRAMMY-winning album, The Miseducation of Lauryn Hill, and bringing out Pras and Wyclef Jean for a Fugees reunion. 

Sunday featured high-powered performances from soulful songstress Ari Lennox, former Ruff Ryders first lady Eve, and the devastating femmes of South Florida, the City Girls. Philly’s own DJ Drama drew out home-grown talents like D-Surdy, Armani White, and Bronx legend Fat Joe on the Presser stage. 

To close out the weekend, Usher brought the magic of his Vegas residency to West Philly for a string of era-defining hits in the twilight of the festival. Read on for some of the most captivating moments and exciting sets from the 2023 Roots Picnic. 

GloRilla Shines In Roots Picnic Debut

GloRilla | Kayla Oaddams/Getty Images

Unapologetic rebel GloRilla may have just one EP under her belt, but her growing fandom came alive during her Roots Picnic performance.

The Presser Stage crowd swooned along with femme-empowering smashes like "Phatnall," as well as more provocative songs like "Nut Quick" and "Lick or Sum." Legions of newly single fans  screamed the lyrics to crunk hit "F.N.F. (Let’s Go)." 

Big Glo kept the momentum going at high speed, loosening the relatively stiff crowd. And while Cardi B wasn’t present for her part in "Tomorrow 2," GloRilla brought out an energized and visibly pregnant Chrisean Rock for a twerk-worthy cameo. 

GloRilla truly embraced her rowdy nature and southern charm, which has helped her earn garner recognition from her peers and even notch her first GRAMMY nod for Best Rap Performance. 

Usher Brings Sultry And Sin To The City, With A Few Special Guests

Usher and Black Thought perform | Taylor Hill/Getty Images for Live Nation Urban

Before Usher had even closed out the festival, radio and podcast personality Charlamagne and comedian Jess Hilarious talked about wrapping up their own event early to snag a close seat to watch the R&B star in action.

Though decades into his musical career, Usher hasn't missed a step. Dressed in leather, the eight-time GRAMMY winner delivered his classic, slow-burning album cuts and glossy radio hits under the glimmering lights of the open air Park stage. 

Usher put on an electrifying performance that covered hits from various eras in his catalog. Songs like "Love in This Club," "U Don’t Have to Call," and "Lil Freak" had Sunday’s crowd staring in awe, even for those looking to get ahead of the departing traffic. He also brought The Roots on stage before Philly natives Jazmine Sullivan, Eve and Black Thought joined the singer to perform "U Got Me." 

Lauryn Hill (And Some Famous Friends) Took The Crowd Way Back 

Wyclef Jean, Lauryn Hill, and Pras Michel of the Fugees | Taylor Hill/Getty Images for Live Nation Urban

Lauryn Hill’s reputation precedes her. Some fans joked about her tardiness — or even potential absence — but the legendary vocalist arrived about 30 minutes past her scheduled set time and put on a performance that was met with shockwaves of cheers.

Hill's headlining performance coincides with a big milestone: the 25th anniversary of her groundbreaking album The Miseducation of Lauryn Hill. "Even though it's been 25 years, everything is still everything," she told the enlivened crowd. 

She performed tracks from the masterful GRAMMY-winning album, including "Everything Is Everything" and "When It Hurts So Bad," but perhaps the biggest surprise throughout the weekend was the reunion between her, Pras and Wyclef Jean. The trio came together as the Fugees to perform hits "Ready Or Not" and "Killing Me Softly" for a spirited celebration of the group’s 1996 album The Score. 

"We’re out here doing 25 years of Miseducation. But there’s another 25 years we didn’t do a couple of years ago because of COVID," Hill said of the group’s project. The group closed out with "Fu-Gee-La," with Hill switching from her soothing alto to her "L-Boogie" persona of old, bringing the joyous crowd to its knees. 

City Girls Bring The Twerkers Out To Play

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The City Girls brought headliner energy to Sunday’s picnic, with JT and Young Miami inciting a twerkathon with hot summer girl anthems like "Act Up" and "Do It On The Tip" playing out center stage. 

The Miami duo kept the energy high with on-stage twerk moves, pulsating hits like "Twerkulator," and efforts to draw out the crowd’s inner act-bad attitude by screaming: "If you’re a bad bitch, say, ‘Hell, yeah!’" And by the end of the group’s performance, fans were left with a racing heartbeat or sweating from the constant flow of high-powered hits and go-get-him-girl records. 

Lil Uzi Vert Knows What The City Wants

Lil Uzi Vert | Taylor Hill/Getty Images for Live Nation Urban

Now in their third appearance since 2016, Philly native Lil Uzi Vert took to the Park stage on Saturday, bringing enough bass and adoring screams that could be heard across Fairmont Park. 

 "I ain’t going to do too much talking. Let’s do it," they said to the roaring crowd. While Lil Uzi’s voice occasionally drowned in a song’s instrumental, their effortless magnetism and signature shoulder roll dance brought excitement to the growing crowd. 

The rumblings of hits like "444+222" and "Sauce It Up" rang in fans’ ears, and songs like "Money Longer," and the Diamond-selling smash "XO Tour Llif3" nearly turned portions of the crowd into mosh pits. Lil Uzi’s performance came to a welcomed halt when fans were invited to the stage to dance to the massively popular "Just Wanna Rock," which has become an unofficial anthem in their hometown. "I’m in the city, this they s—."  Fans pulled out their phones as the rap star capped off the set with the viral hit. 

Lucky Daye Drips In Allure

Only a year removed from his breakthrough album, Candydrip — a genre-drifting and soul-stirring project riddled with pop and R&B hits — Lucky Daye has risen to star status. And with songs like "Real Games" and "Late Night," it’s easy to be drawn to the New Orleans-born artist. 

While initially draped in glimmering red garments, it didn’t take the artist long to strip down (well, shirtless, that is), and render impassioned vocals over the cheers and screams of his admirers. He dove into songs across his various albums and fell to his knees to deliver a burningly passionate rendition of "F—kin’ Sound" before the 37-year-old vocalist exited the Mann’s amphitheater stage.

Ari Lennox Conjures Soul In Comforting Fashion

Ari Lennox | Taylor Hill/Getty Images for Live Nation Urban

It’s unclear if Ari Lennox still has plans to step away from the touring circuit for good, but if her Sunday evening performance is any indication,  her presence would be sorely missed. The "Shea Butter Baby" vocalist conjured every fragment of her soulful and poetic artistry, bringing vibes despite having a slight cold.   

The DC-born R&B singer danced to the flowy breeze setting over the stretched-out crowd while singing favored tracks like "New Apartment," as well as "Waste My Time" and "Pressure" from last year’s Age/Sex/Location. Lennox encouraged fans to close their eyes and sway their hips, and many raised drinks as Lennox’s soothing voice and sultry lyrics wrapped around their bodies.

Busta Rhymes And Eve Come To Devastate

Spliff Star and Busta Rhymes | Taylor Hill/Getty Images for Live Nation Urban

Joined by The Roots’ Black Thought, Busta Rhymes and Spliff Star tore down the Park stage, even with distracting audio woes hindering the early part of their set. Shot mic or not, Busta’s lion-like voice could be heard from yards away as he spewed the lyrics to "Put Your Hands Where My Eyes Could See" and A Tribe Called Quest’s "Scenario" to a cheering audience. 

Eve arrived during the latter part of the DJ J. Period curated set. The former First Lady of Ruff Ryder burst onto the stage and held her own alongside the fellow hip-hop heavyweights. As she swayed the crowd with songs like "Tambourine" and her verse on the late DMX’s "Ruff Ryders Anthem (Remix)," it harkened back to her days as a lyrical wild card in the early 2000s before she ventured into acting and hosting gigs. 

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Brandi Carlile has been making waves in the Americana community for nearly two decades. But in 2019, Carlile's career began a different — and much bigger — trajectory thanks to a little song called "The Joke." 

The lead single from her sixth studio album, By the Way, I Forgive You, "The Joke" is dedicated to marginalized communities who constantly feel underrepresented and unloved by society. As a trailblazer in the LBGTQIA+ community, her impassioned vocal performance struck fans and critics alike.

In this episode of GRAMMY Rewind, we revisit the day "The Joke" helped Carlile win her first golden gramophone, for Best American Roots Performance. (It was one of three GRAMMYs Carlile took home that night, as "The Joke" also won Best American Roots Song and By the Way, I Forgive You won Best Americana Album.)

"It's our first GRAMMY!" Carlile cheered alongside her longtime collaborators Phil and Tim Hanseroth. "This means so much to me [...] and Dave Cobb, who wrote this song and brought the best out in us. We can't thank you enough."

Carlile went on to praise her team at Elektra Records and her family. "So many people to thank, but I'm violently shaking right now," she added, then passed the mic to the Hanseroth twins. 

Before the trio left the stage, Carlile quipped, "Whoever we forgot, forgive us. You know we love you, and you know we're terrified!" 

Press play on the video above to watch Brandi Carlile's complete acceptance speech for Best American Roots Performance at the 2019 GRAMMYs, and check back to GRAMMY.com for more new episodes of GRAMMY Rewind.

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By the time she released The Miseducation of Lauryn Hill in 1998, singer and rapper Lauryn Hill had already scored two GRAMMY Awards for her work in the hip-hop trio Fugees. Her debut solo album — and only one to date — generated another seven wins, including Album Of The Year and Best R&B Album, which brought rapping to the mainstream in a way previously unseen. And in a male-dominated genre, this feat was achieved by a strong woman.

"This is crazy, ‘cuz this is hip-hop music!" Hill exclaimed when Whitney Houston presented her with the golden gramophone for Album Of The Year at the 41st GRAMMY Awards in 1999.

Hill set a number of records with Miseducation: The lead single "Doo Wop (That Thing)," released two weeks before the album, immediately went to No. 1 on the Billboard Hot 100 and Hot Rap Songs chart. As a woman solo artist, she set long-held records for both charts with "Doo Wop (That Thing)." The album also entered the Billboard 200 chart in the top position, which no other debut from a woman had achieved before.

Miseducation contains 16 songs and is over 77 minutes in length — a long album by modern standards, yet fitting for Hill’s magnum opus. The album features guest appearances by Carlos Santana ("To Zion"), Mary J. Blige ("I Used to Love Him") and D’Angelo ("Nothing Even Matters"), bringing listeners back to the classroom for interludes where Hill schools the world on what a vanguard looks like.

And Lauryn Hill was at the vanguard in many ways. Several women who were popular in mainstream hip-hop at the time favored scantily clad outfits and scandalous lyrical content, but Hill projected the opposite in songs about love, faith, fortitude and empowerment. Throughout Miseducation, Hill talks to God and to the world, while simultaneously issuing warnings for those who have mistreated her.

Twenty-five years later, Miseducation still sounds vibrant, alive and current. That’s a testament to how influential Hill’s work continues to be not only in popular music, but in pop culture and womanhood — especially for Black women and single mothers.

"I think the piece as a whole communicates my personality, it is the culmination of my experiences, the sum total of what I had gone through at a certain point in my life," Hill told The Guardian in 2013. "To me it's like driving in a storm, it's hard to see where you're going. You're just praying to get out of it. But once you get out of it, you can look back and say; ‘Oh man, thank god!’ Give thanks, 'cos that's what I came out of. That's what that album feels like to me."

"Doo Wop (That Thing)," "Ex-Factor" and "Everything Is Everything" were each accompanied by masterful music videos that showed Hill as a woman who transcends the ages.

Speaking To Women

For women who were faithful hip-hop fans despite a prevailing tide of misogyny and death, as well as those facing single motherhood, Miseducation demonstrated a positive and empowered way forward. Instead of catering to the male gaze, the songs spotlight the joys and the struggles of women with rugged beats and lyrics that highlight her pure skill as an MC.

"Lost Ones" asserts her split from Fugees with the bravado of the best wordsmiths, while "I Used to Love Him" with Mary J. Blige samples the very macho "Ice Cream" by Wu-Tang Clan rappers Raekwon, Ghostface Killah, Method Man and Cappadonna. And songs such as "Doo Wop (That Thing)" and "To Zion" showcase her powerful abilities as a singer, a potent accompaniment to her rhymes.

"Lauryn was a breath of fresh air, a hope and — unrealistically — a solution to what was wrong with hip-hop and its representation of women at the time," Joan Morgan, author of She Begat This: 20 Years of The Miseducation of Lauryn Hill, said in a 2018 interview with VIBE. "I think people hold dear to it as a really exciting possible moment of change, which in some ways wore itself out and in some ways didn’t. It does more work than just an album…It’s like running into an old friend that you don’t necessarily keep in touch with all the time, but one you have really fond memories of."

"It wasn’t until much later that I realized how many women and girls were changed by the album," Thembisa S. Mshaka, who worked as the senior advertising copywriter for Sony Music during the album’s release, told Okayplayer. "I was shocked to learn how many of the women I’d meet throughout my career still had point-of-purchase flats of the cover, or posters, or ads ripped from magazines like Honey and VIBE on their walls. Lauryn was that role model for the hip-hop generation that Diana Ross was for the Motown generation."

The Pressure

Hill immediately faced monumental pressure from fans and the music business to produce more music after Miseducation. She later shared that the squeeze was taking a toll on her art. 

"I had to step away when I realized that for the sake of the machine, I was being way too compromised," she explained in a 2006 interview with ESSENCE. "I had to fight for an identity that doesn’t fit in one of their boxes. I’m a whole woman. And when I can’t be whole, I have a problem. By the end I was like, I’ve got to get out of here."

Though fans keep hope alive, Hill has never released another album, which makes Miseducation even more significant with the passage of time.

"People need to understand that the Lauryn Hill they were exposed to in the beginning was all that was allowed in that arena at that time," she continued to  ESSENCE. "There was much more strength, spirit and passion, desire, curiosity, ambition and opinion that was not allowed in a small space designed for consumer mass appeal and dictated by very limited standards."

Hill gave Miseducation her everything, and while she hasn’t released more albums, she has performed songs from the album live countless times over the years. She keeps the material fresh for herself by constantly creating new arrangements, tempos and vibes for the songs, and fans will be able to check that out when she celebrates the 25th anniversary of the album with special performances of the work at Roots Picnic in Philadelphia (June 3-4), Wolf Trap near Washington, D.C. (June 9), Ravinia Festival in Highland Park, IL (June 17) and ESSENCE Festival in New Orleans (June 29-July 3).

"People can be disappointed that we haven’t had more music from her, but I don’t know if they can blame her or be angry," Morgan added in her VIBE interview. "We’re not entitled to another album — I think audiences forget that," she remarks. "You can’t be angry with someone because they only gave you one of what you wanted." 

Responding To Persisting Controversy

A 1998 lawsuit filed against Hill by Johari Newton, Tejumold Newton, Vada Nobles and Rasheem Pugh alleged that the star didn’t credit their musical contributions to Miseducation. The suit was settled out of court, but accusations outside the legal arena have persisted over the years.

In 2018, Hill posted a written response to pianist Robert Glasper’s claims that she uses work from others without crediting them. In it, she acknowledged that it took the work of others to bring her vision to life, but asserts that she is the nucleus, and that she hired musicians to execute her specific ideas. 

"The album inspired many people, from all walks of life, because of its radical (intense) will to live and to express Love," she countered in the response, which was posted to Medium. "I appreciate everyone who was a part of it, in any and every capability. It wouldn’t have existed the way that it did without the involvement, skill, hard work, and talents of the artists/musicians and technicians who were a part of it, but it still required my vision, my passion, my faith, my will, my soul, my heart, and my story."

A quarter century later, The Miseducation of Lauryn Hill remains timeless. It has been prominently sampled by major artists who followed, including Drake, Cardi B, Lizzo, H.E.R. and J.Cole. The beauty of this iconic album is that it may well spark the brain of the next musician who will make as much of an impact on music and humanity.

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When Dolly Parton, flanked by Brad Paisley, handed Faith Hill her GRAMMY for Best Country Album in 2001 — for her classic 1999 album Breathe — it felt like a passing of the torch.*

The first words out of an awestruck Hill's mouth, to Parton: "Wow! And coming from you, thank you so much. I just admire you so much."

Hill went on to deliver a heartfelt speech, in which she thanked her parents for helping facilitate her music dreams and expressed how long and hard her journey to the GRAMMYs stage was.

Breathe helped Hill take home three GRAMMYs that night — the others being Best Female Country Vocal Performance ("Breathe") and Best Country Collaboration With Vocals ("Let's Make Love," with three-time GRAMMY-winning husband Tim McGraw.)

Check out the throwback to Y2K-era country music history above, and keep checking back to GRAMMY.com for more episodes of GRAMMY Rewind.

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