Etymology

with blackjack and hookers

Today it means: Improved, enhanced; said of a new competing product or service compared to an existing one. Full definition →

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The story

From the episode "The Series Has Landed" (1999) of the American animated sitcom Futurama, which includes a running gag involving the robot character Bender stating that he will build his own versions of tourist attractions after being excluded from them, but "with blackjack and hookers" added.

Etymology from Wiktionary, CC BY-SA 4.0.