pimp cup n. an ornately decorated goblet resembling a trophy. (source: Double-Tongued Dictionary)
Further reading
juicy noun. A person who illicitly carries alcohol in a water bottle. «Gwen Alexander, who’s been working at the Astoria pool for two years, confirms there haven’t been any issues with fighting this year but she said rule enforcement is...
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I believe all of this “pimp cup” business started in emulation of former pimp Don “The Magic” Juan, who carries around a big chalice of “pimp juice”. He was featured in the 1999 HBO documentary, “Pimps Up, Ho’s Down”.