Dilemma: Why Nelly Is Right About The Toughest Era In Hip-Hop

Initially debuting in 2018, The Shop started as a talk show where NBA legend Lebron James and a series of guests would gather in barbershops to discuss various topics openly and earnestly, not unlike what happens every day in barbershops and beauty salons across the country. 

The seventh season came out on March 7, 2024. While King James was absent from this episode, the show’s premise remained unchanged. And one of the most memorable statements came from rapper and philanthropist Nelly when he said:

“But you gotta understand, my era of music was the toughest era in hip-hop ever. Ever. When I put out songs, I had to go against DMX, Jay-Z, Eminem, Lil Wayne, 50 Cent, [and] Luda. All of us are fighting for one spot. So from ’99 to 2008-10, it’s the hardest era ever.”

Nelly’s statement begins at approximately 19:46 into the program.

A Primary Source

Art is subjective, but there is substantial merit to Nelly’s claim here. As someone born in ’87, I was hip-hop’s primary demographic during this time frame, and I can attest that it was an era in rap that was never seen before and has yet to happen again since. And unlike the digital music landscape of 2024, where a monthly subscription fee provides blanket access to millions of songs, before the turn of the millennium, consumers were paying the equivalent of that (if not more) for just an LP’s worth of songs by a single artist or group. Therefore, the music had to be on point. And it was. As the saying goes, “Men lie. Women lie. Numbers don’t.” And these albums sold by the hundreds of thousands week after week.

The Last Breath of the 90s

Even going into 1999, hip-hop was in uncharted territory. On December 22, 1998, DMX released his sophomore set, Flesh of My Flesh, Blood of My Blood. When it debuted at number one on the Billboard 200, X made history by becoming the first living hip-hop artist to debut two albums at the top of the charts in the same calendar year (X’s first album, It’s Dark and Hell is Hot debuted at number one in May 1998).  Flesh of My Flesh stayed on top for three consecutive weeks leading into the following year.

“Slippin'” was the first single from DMX’s Flesh of My Flesh, Blood of My Blood.

The next major release came one month later, in February 1999, with the arrival of Eminem’s major label debut, The Slim Shady LP. And his impact was immediately felt. Last year, on the Rap Radar podcast, Fat Joe even told a story about how he and Big Pun stood in line at Tower Records in Los Angeles the day before the 1999 Grammys, where Pun was nominated, to get a copy of it. In this same interview, Joe refers to Em as a “rap god.” He isn’t incorrect in this assessment either. Eminem, a protege of Dr. Dre, has since become the most commercially successful hip-hop artist in history and one of the genre’s most critically acclaimed.

The Dawn of the 21st Century

Jay-Z broke onto the national scene in 1996 with his single, “Ain’t No Nigga,” after it appeared on The Nutty Professor soundtrack.  However, in the fall of 1998, Jay’s third album, Vol. 2… Hard Knock Life, propelled him into the mainstream, and he has been on an unprecedented ascent ever since. But even back in ’99, Jay-Z knew his worth. (He didn’t spit the first verse for the lead single off his next album, Vol. 3… Life and Times of S. Carter.) And in one of the most masterful moves in hip-hop marketing history, the label, Def Jam, set it up so they would have the last number-one album of the 20th century (DMX’s third offering …And Then There Was X) and the first number-one album of the 21st (Jay-Z’s Vol. 3).

“Big Pimpin'” was the final single from Vol. 3… Life and Times of S. Carter and featured UGK.

How The West Was One

West Coast hip-hop was far from down and out, either. In November 1999, Dr. Dre released 2001, the long-awaited proper follow-up to his landmark debut, The Chronic. It did not disappoint. The 22-track collection solidified Dre’s stature as a musical genius. It also nurtured talent from a then-up-and-coming producer/piano player named Scott Storch. Additionally, it reignited Snoop Dogg (who would release the stellar Tha Last Meal in late 2000). And it continued to propel left-side lyricist Xzibit to a broader audience. Then, when “Forgot About Dre” was released as a single in January 2000, it proved Eminem would be a mainstay and helped set up Mr. Mathers’ colossal next album, which would drop just four months later.

Footage of Dr. Dre and Eminem performing “Forgot About Dre” on The Up in Smoke Tour in 2000.

Country Grammar

Nelly’s first album, Country Grammar, hit shelves on June 27, 2000. It entered the charts at number three. After surfing the top ten most of the summer, it finally got that number-one slot in August. By October of that same year, the album had sold an astonishing three million copies- a challenging task for anyone, let alone a relatively unknown rapper from MO. However, that success is proof of Nelly’s quality sound, style, and artistic integrity. One of the things that made that album such a hit was that it was original. It sounded different from the East Coast, the West Coast, and the South. 

During a documentary commemorating the 20th anniversary of Country Grammar, Nelly said, when speaking on the sound of the Midwest, “We like to say, ‘You get the best music from the Midwest because we’re everything.’ We’re everything. We’re the East, we’re the West, we’re the South. He added, “You would hear people who had skills lyrically, but also melodically, cadence-wise.”

While the title track, the lead single from Nelly’s debut, introduced this melting pot of sonics to its audience, the album’s third single, a collaboration with St. Lunatic rapper City Spud, “Ride Wit Me,” most effectively brought it all together. The song peaked at number 3 on the Billboard Hot 100. And it would be Country Grammar’s strongest performing single.

The music video for “Ride Wit Me” won “Best Rap Video” at the 2001 MTV Video Music Awards.

2001

In the fall of 2000, a former Atlanta radio DJ turned rapper, Ludacris, burst onto the scene based on his major label debut, Back for the First Time, and its hit song, “What’s Your Fantasy.” That served as a true testament to his success as an independent artist since that album is his debut album, Incognegro, repackaged with the addition of a few extra tracks. One was the project’s second single, “Southern Hospitality,” officially released at the beginning of 2001 and produced by The Neptunes. Luda’s following three albums were also multi-platinum sellers.

The first half of 2001 was relatively quiet for hip-hop. But Nelly continued to represent his crew, the St. Lunatics, and Midwest rap with the release of the group’s first and only LP, Free City. Then, at the end of the year, in addition to continuing to cope with a national tragedy, the battle between Jay-Z and Nas consumed hip-hop, and that garnered lots of attention for their albums (The Blueprint and Stillmatic respectively ). The war of words also resulted in two of the best diss records ever, “Takeover” and “Ether.”

Ron Browz, producer of “Ether,” got the beat to Nas because Browz’s manager ran into Nas’ travel agent.

Nellyville

“Hot in Herre” was released on May 7, 2002. It would become Nelly’s first number-one hit. On June 25, 2002, the album it appeared on, Nellyville, dropped, as did the project’s second single, “Dilemma.” Nellyville was the top-selling album in the country for three weeks in a row. “Dilemma” with Kelly Rowland was also a chart-topper. It even won the Grammy for “Best Rap/Sung Performance” in 2003. 

 Another sign of Nelly’s increasing success was the features on the Nellyville album. In addition to Kelly Rowland, as mentioned earlier, and the St. Lunatics, Nelly enlisted the aid of Justin Timberlake (“Work It”) and Beanie Sigel and Freeway (“Roc the Mic [Remix]”). While that guest list is small, it’s still very noteworthy. Kelly and Justin were part of two of the most prominent groups in popular music at the time. Then Beanie and Freeway were attached to the East Coast rap label that every aspiring rapper wanted to sign with, Roc-A-Fella Records. 

“Hot in Herre” was number 36 on the Billboard Hot 100 decade-end chart performance (2000-2009).

2003 – 2005

From 2003 to 2005, the rap game belonged to 50 Cent and G-Unit. 50’s first official offering, Get Rich or Die Tryin’, would go on to sell nine million copies in the United States alone. Then the G-Unit label, group, and brand 50 set up with it led to platinum and gold plaques for everyone associated, including The Game, Lloyd Banks, Young Buck, and Tony Yayo. When 50 Cent’s next album, The Massacre, came out in 2005, it became the biggest-selling album in a short week, with sales at the 1.14 million mark after only four days.

However, between Fif’s two blockbuster albums, Nelly held his own with unconventional releases on the same day in September 2004. He released the Sweat and Suit albums. As the titles suggest, the albums have opposing themes. The difference in sales was over 50,000. (Suit debuted at number 1 with sales of 396,000 and Sweat at number 2 with 342,000.) Even still, most consumers seemingly went out and purchased both. And while many would argue that Suit was critically superior too – thanks in part to the Tim McGraw-assisted “Over and Over,” Sweat still had its moments (notably when Nelly recites Tupac lyrics from “2 of Amerikaz Most Wanted” on “Na-NaNa-Na”). 

50’s “P.I.M.P.” first appeared on his debut and has gotten a resurgence in popularity recently because of the 2023 film, Anatomy of a Fall.

2006 – 2010

Lil Wayne’s debut came out in 1999. But between his fifth and sixth studio LPs (released in 2005 and 2008), his self-proclaimed “Best Rapper Alive” title earned credence. Not only had he shown continuous improvement throughout his career, but his phenomenal work on mixtapes made him the number-one rapper, and he didn’t even have a “new” album out. So when Tha Carter III hit, it sold exceptionally well, tallying over one million in its first week in June 2008.

The following September, Nelly released Brass Knuckles. Despite the moderate success of a few of its singles, the album failed to gain traction like his previous releases. Even with some socially conscious lyrics ( “They say I’m old enough to go to war / But I ain’t old enough to play in the NBA no more / Now you tell me, what’s wrong with that? / I pledge allegiance all the way to Iraq / But ain’t nobody pledging to me when I get back”), it couldn’t make up for Nelly’s usual formula that saturated most of the album. And at this point, it was getting played out -albeit only because he had previously done it so successfully.

Then, in February 2009, hip-hop noted a mixtape called So Far Gone by Canadian rapper Drake. The project was so successful that a major label reissued it later that year as an EP. With that, a new chapter in hip-hop began, and Drake became one of music’s most successful recording artists and one of the brightest stars of hip-hop’s next generation. In addition to the decade, 2009 also closed out an era in hip-hop, especially when Drake’s first full-length LP came out in June 2010.

Da Drought 3 received a positive response from critics and fans when it was released in 2007.

Conclusion

1999 – 2010 was an extraordinary period. All the artists Nelly named (and others like T.I., Young Jeezy, and Kanye West) have reached legendary status and remain relevant today. Props go to 70s hip-hop for laying the foundation, 80s hip-hop for turning it into a business, and 90s hip-hop for winning the culture war. However, in the decade after that, with the most money, control, technology, and demand ever, hip-hop capitalized on its power and created the most rewarding (hence, competitive) environment the genre has seen thus far. For example, three of those previously mentioned rappers [plus Nelly himself] have even performed at the Super Bowl Halftime Show, with Ludacris appearing there as recently as last month. And fingers crossed that Lil Wayne gets added to that prestigious list when the Super Bowl occurs in New Orleans in 2025.

Therefore, that also makes the point that hip-hop now not only has a fan base as a result of its youth-driven appeal but a multi-generational reach like never before because more adults than ever grew up with rap as part of the fabric of their lives, as opposed to generations past where it was still finding its place within society. And now, these individuals are making decisions about things where hip-hop historically had been sidelined (i.e., mainstream branding, broadcasts, advertisements, sponsorships, politics, etc.). However, as recent events have shown, a shift has occurred because of hip-hop’s influence over the last few decades, and the jury is still out on everything from 2010 forward.

In other, and not so many, words, Nelly is right. He came up in hip-hop’s toughest era to be number one (and he became that. And he went diamond)! Respect due.

Cause two is not a winner, and three, nobody remembers.

An excerpt of the Super Bowl LVIII Halftime Show.