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Hipster Hop and The Plight of the Modern Rapper

Updated on April 1, 2012
"Lupe Fiasco and Fat Joe Look-A-Like from concert I went to."
"Lupe Fiasco and Fat Joe Look-A-Like from concert I went to."

An acquaintance once asked me the following question: "Hey Justin, can you tell me why every single hip-hop song is about how snug the pants are 'cuz they be full of money?" It was an innocent question of course. Rappers are widely known as some of the biggest braggarts of both wealth and "fly" denim wear. However, in seriously contemplating the answer, I realized that "money" and "snug pants" have far greater meaning and association across the vast history of hip hop. And moreover, "money" inside of "snug pants" nicely explains a generational disconnect between modern rap artists and older rap masters. Allow me to elaborate.......

"Kriss Kross a make ya Jump, Jump."
"Kriss Kross a make ya Jump, Jump." | Source

Vive la Saggy Pants!

During the 90’s and early 2000’s, baggy/saggy pants were of course…in vogue. Engendered by the national prison system’s “no belt” policy, made popular by such popular acts as LL Cool J, provided by fashion conglomerates such as Sean John and taken in a weird direction by 13 year old rap group Kriss Kross (seen in picture on right), the saggy pants style became the symbol of urban plight and struggle. Theories also abound that saggy pants enabled up and coming gangsters and OGs to better hide concealed weapons, illegal contraband and money; therefore implying that the saggier the pants, the more money held by said gangster. A point further emphasized by made man Rick Ross in his hit single MC Hammer:

Diamonds moving on my chest, wanna Hammer dance.
Seventy grand make my jeans sag like some Hammer pants.

And then they started wearing the oversized long shirts…Thank God that’s pretty much over.

Meantime, the seeds of the tight pants movement were slowly being planted. The recession and resulting recovery of late 2000-2003 made the extra fabric of saggy pants more impractical (than it had already been) and more expensive. Inner-city violence continued its 90’s era decline, negating the need for portable concealment gear. Gangstas young and old were now more interested in skateboarding and working on their burgeoning rap careers. In fact, I believe we are actually still living through this era of Pax Hipstera.


Out of this era has come a number of talented lyrical acts: Wiz Khalifa (seen above), the newer Lil Wayne, Drake, and Lupe Fiasco and Kid Cudi to name a few. These new acts have successfully combined elements of hipsterdom and hip hop to form hipster hop, a more sing songy—club friendly form a rap highly criticized by the hip hop old guard. Observe the following lyric from the Jay-Z song DOA (Death of Autotune):

Stop your blod clot crying
The kid, the dog, everybody dying, no lying
You niggas’ jeans too tight
Your colors too bright, your voice too light.”

To show more of their mettle, or to distinguish themselves from hipsters completely…some artists have dedicated themselves to keeping it “thugga” by referencing the hallmarks of the 80’s/90’s gangsta. Introduce T-Pain, an artist whose authenticity (origin of voice and dreds) is frequently put to question, rapping about jeans full of cash-money or some fantasy currency called gwap:

Shawty what I gotta do to get you home
My jeans full of gwap
And they ready for Shones
Cadillacs Maybachs for the sexy grown
Patron on the rocks that’ll make you moan. “


So “money inside of snug pants” -- Is it the chest-thump grandstanding typical of most rap fare…yes. But it is also more evidence of an identity crisis facing hip hop and the newest artists to emerge. Just some food for thought.


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      Talkinbull 5 years ago

      Black Hip Hop culture in the US has replaced what was once the optimistic and flash white culture of the 50s/60s, big cars, big money etc. White US culture now shows itself as angst conservatism of Prius' and Credit Crunch. Flo Rida and Snoop brag about their Cribs, Gold and Huge wheels so did the mainstream white middle classes with there Suburban Palaces, Golf Culture, Cadillacs, as for Gansta? Well you had Frank Sinatra. Culture stays the same just the Black Hip Hop culture has rightfully claimed their share of it.