The 1990s File Feature
Enjoy Yourself
A+ and "Enjoy Yourself": A Young Rapper's Second Moment on the National Chart The late 1990s hip-hop landscape was defined by an extraordinary concentration …
01 The Story
A+ and "Enjoy Yourself": A Young Rapper's Second Moment on the National Chart
The late 1990s hip-hop landscape was defined by an extraordinary concentration of talent and commercial activity, with artists at every level of the industry competing for radio play, retail space, and audience attention. Within this competitive environment, a teenager from Yonkers, New York, born Azie Johnson Jr. and recording under the name A+, managed to establish a foothold that distinguished him from the countless other young rappers attempting to break through during the genre's commercial golden age. His trajectory in 1998 illustrated both the opportunities available to talented young artists in the era's expansive hip-hop market and the formidable challenges of sustaining momentum in a genre that moved quickly and discarded its arrivals with equal speed.
A+ had first registered commercially with his debut single "Enjoy Yourself" in 1998, released through Kedar Entertainment, the independent label founded by Kedar Massenburg that had also developed Erykah Badu and D'Angelo. The label's reputation for supporting artistically distinctive voices gave A+ a credible platform, and his age, still a teenager at the time of the single's release, added a dimension of novelty that helped generate press attention. Youth in hip-hop had always been commercially interesting, and A+ possessed the technical facility and charismatic presence to justify the attention rather than merely benefiting from the novelty factor of his age.
"Enjoy Yourself" entered the Billboard Hot 100 on November 14, 1998, debuting at number 75. Over the following three weeks, the single climbed to its peak position of number 63, reached during the chart week of November 28, 1998. The three-week chart run was modest by the standards of hip-hop's most commercially dominant acts of the period, but it represented genuine mainstream pop chart presence for a young independent artist whose label did not have the promotional machinery of the major-label rap imprints that dominated the charts at the time.
The period context is worth noting in detail. The late 1990s hip-hop mainstream was dominated by the commercial juggernaut of Cash Money Records, Roc-A-Fella Records, and the aftermath of the East Coast-West Coast rivalry's most destructive moments. The deaths of Tupac Shakur in 1996 and Notorious B.I.G. in 1997 had cast a shadow over the genre while simultaneously driving an enormous commercial response as the industry poured resources into developing new acts. In this environment, a young rapper with genuine technical skills and a positive, pleasure-oriented message had a particular kind of appeal that cut against the more confrontational strains dominating commercial radio.
A+'s approach was characterized by an energy and accessibility that positioned him as a celebratory voice rather than a combative one. His youth was reflected not as naivety but as genuine exuberance, a quality that could feel fresh against the harder edges of the genre's commercial mainstream. Kedar Entertainment's promotional strategy recognized this positioning and worked to distinguish A+ as an artist with broad appeal beyond the core hip-hop demographic that defined the genre's sales base.
The single's chart performance confirmed that this positioning had commercial validity, even if the three-week run suggested that the broader pop audience had not yet been fully converted. Hip-hop's relationship with the pop mainstream in 1998 was complex: the genre dominated commercial music in terms of cultural visibility and retail sales, but the specific crossover to pop radio airplay that drove extended Hot 100 runs remained a more selective process, favoring tracks that incorporated melodic elements or pop production strategies alongside traditional rap aesthetics.
The legacy of A+'s brief Hot 100 moment belongs to a specific category of hip-hop history: the talented young artist whose commercial presence registered meaningfully in the documented record of the era without achieving the sustained stardom that the initial evidence of talent might have predicted. The pop chart tells a story not only of careers that lasted but of moments that mattered, and A+'s November 1998 chart entries with "Enjoy Yourself" represent a real commercial achievement by an artist who engaged genuinely with the genre's possibilities at a critical moment in its development.
02 Song Meaning
Youth, Pleasure, and Hip-Hop Celebration: The Meaning Behind A+'s "Enjoy Yourself"
A+'s "Enjoy Yourself" operates within the celebratory tradition of hip-hop that positions music and its associated pleasures as fundamental goods deserving direct expression. The track belongs to a lineage of party-focused rap that stretches from the genre's earliest days back to the block parties of the Bronx in the 1970s, carrying forward the essential idea that hip-hop at its most elemental is a music of communal celebration, of the assertion that life is worth enjoying and that the enjoyment of it is itself a legitimate subject for artistic expression.
That A+ was a teenager when the record was released gives the track a particular kind of authenticity. His expressions of youthful energy and pleasure-seeking were not a persona adopted for commercial purposes but a genuine reflection of his actual life stage and outlook. This quality of age-appropriate authenticity is rarer than it might seem in commercial hip-hop, where artists are sometimes pressured to adopt postures that project a hardness or experience inconsistent with their actual situations. A+'s youth was an asset precisely because it was real.
The song's title and thematic content connect it to a broader cultural conversation about how young Black men in America navigate between the expectations placed upon them and their own desires for pleasure, freedom, and self-expression. Hip-hop in the late 1990s was engaged in this conversation at multiple levels, from the most commercially oriented party rap to the most politically conscious underground material. "Enjoy Yourself" participates in this conversation from the pleasure-affirming end of the spectrum, but that position carries its own kind of statement: that joy is not frivolous but essential, that the capacity to enjoy one's life is something worth asserting and defending.
Kedar Entertainment's aesthetic sensibility, shaped by its work with artists like Erykah Badu and D'Angelo who were central to the neo-soul movement, gave A+ a musical home that valued a certain warmth and accessibility alongside hip-hop's characteristic energy. The production on "Enjoy Yourself" reflected this environment, creating a sonic context that was welcoming rather than confrontational, built for inclusion rather than exclusion. This approach positioned the song for the broadest possible audience appeal, which the Billboard Hot 100 performance, peaking at number 63, confirmed had some commercial validity.
The song also participates in a specific hip-hop rhetorical tradition: the direct address to the listener, the invitation to join the speaker in a shared activity or state of being. This kind of inclusive address creates a sense of community between artist and audience that distinguishes it from more self-referential or inward-looking hip-hop modes. The listener is not an observer of A+'s experience but a potential participant in it, which contributes to the accessible, welcoming quality that defined the track's commercial positioning.
Within the context of late 1990s hip-hop's extraordinary commercial expansion, "Enjoy Yourself" represents a specific aesthetic choice: positivity over aggression, celebration over confrontation, inclusion over exclusion. That these choices did not produce a major commercial breakthrough for A+ reflects the complexity of the marketplace rather than any failure of the artistic approach. The track found its audience and documented its moment on the national chart, adding its specific voice to the rich and varied chorus of what hip-hop was doing in the final years of the twentieth century.
→ More from the 1990s File
View all 1990s hits →
Keep digging