The glamour of Hollywood has a tendency to cloud another facet of its biggest stars: their business ambitions. While acting is their main source of stardom, many actors and celebrities have dabbled in as varied ventures as casinos, restaurants, fitness, technology, and health. For some, they have turned into global empires, but for others, they have faced setbacks that suggest that stardom does not equate to business success.

Jay-Z and the Casino Bid That Was Rejected

In September 2025, Jay-Z’s high-profile bid to construct a New York Times Square casino was rejected by a state advisory committee. Jay-Z, with Caesars Entertainment and SL Green Realty, had envisioned a massive entertainment complex with a casino, hotel, and nightlife spots under his Roc Nation brand. While Jay-Z might hav

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