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In 1994, when I heard my beloved game show Jeopardy! was searching for college contestants, I somehow convinced my parents to finance a family trip to Orlando, Florida, where we’d make a holiday of the audition and take a trip to Disney World. If I didn’t pass the 50-item, fill-in-the-blank test, at least we’d have time with Mickey Mouse and each other.

Despite passing the test, though, I didn’t make it. And I took it personally. How many cute Black girls like me did they have on the show? I decided that the next year, when I was a 20-year-old junior at the University of North Carolina at Chapel Hill, I’d find my way to the nearest tryout. My college suite mate, a young Trinidadian woman of Chinese and African descent, was bemused that I planned to skip classes—something I never did—for the opportunity.

She teased me about “my big brain”—a stray comment that would later seem weirdly prescient. I didn’t know it then, but my appearance on Jeopardy! would become a vehicle for my understanding the depth of American...