Before Jay-Z was a billionaire, he was already a regular at Manny’s New York in the Diamond District where Tito Caicedo was making jewelry pieces for the likes of Tupac, Biz Markie and Biggie, who bought three Jesus pieces there. Tito is widely considered the first jeweler of hip-hop, known for crafting bigger, bolder pieces that the street economy gravitated toward. Jay namechecked him directly on Reasonable Doubt‘s “Politics As Usual,” rapping about taking his “fritos to Tito’s.” After Biggie’s murder, Jay-Z wore Biggie’s Tito-made Jesus piece as a recording ritual, a good luck charm he carried into his most important sessions.
The real inflection point came when the Roc discovered Jacob Arabo, better known as “Jacob the Jeweler.” Where Tito spoke the language of the block, Jacob started teaching his clientele about diamond grades and GIA certification — and suddenly everything got more sophisticated. And more expensive. When a new artist was signed to Roc-A-Fella, they received a $100,000 Jacob-designed Roc-A-Fella chain to commemorate the occasion. Jay surely understood the language of bling as a visual signifier and a way to pledge allegiance to the Roc.
“I dipped in the stash, splurged on a chain / Now I’m Titanic, Iceberg’s the name”
Jay’s self-mythologizing was peak late ’90s, when he was stacking aliases and letting the wordplay do the heavy lifting, while still forming his music-industry mogul persona. He adopted the nickname “Iceberg Slim” and became known for wearing the Italian luxury brand’s signature cartoon-knit sweaters. In the video for 1998’s “Imaginary Players,” Jay rocks an Iceberg “Goofy” sweatshirt. See, goofy’s a good thing.
“I got ’em Iceberg stuff, they thought I knew Snoopy.”
Jay and his then-partner Dame Dash watched audiences mirror the look back at them, driving Iceberg sales to skyrocket, and had an epiphany about their influence on the business of fashion: why let Iceberg get all this business? That question would soon answer itself.
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