Luke Song: Hat's Entertainment! The milliner famous for designing Aretha Franklin's 2009 Inauguration chapeau plays a game about real people and fictional characters with iconic headgear.

Luke Song: Hat's Entertainment!

Luke Song: Hat's Entertainment!

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Luke Song. Courtesy of Luke Song hide caption

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Courtesy of Luke Song

Luke Song.

Courtesy of Luke Song

Millinery seems like a brilliant career choice, right? Everybody's got a head.

Aretha Franklin at President Obama's 2009 inauguration, sporting one of Luke Song's hats. Song ended up selling 6000 replicas of the hat after the event. Ron Edmonds/AP hide caption

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Ron Edmonds/AP

But for Luke Song, the owner of Mr. Song Millinery outside Detroit, it happened by accident. "I wanted to be an artist, but I went the route of biochemistry. A typical route," he told Ask Me Another host Ophira Eisenberg. He quit overnight and went to art school, but still never considered hat design, the chosen profession of his South Korean immigrant parents.

"I needed to make money, so I went to my mom's boutique and I made some hats the only way I knew how." They flew off the shelves, and in six months he had paid off his student loans.

Song had discovered his niche. And then, in 2009, with one famous hat at one big moment in history, his became a household name. "I went from zero to sixty in like, two days," said Song.

Since he clearly knows his way around hats, an Ask Me Another Challenge tasked Song with trying to get a fellow contestant to guess real and fictional characters based on a description of their signature chapeaux.

Heard in Episode 323: Smitten With The Mitten State

This segment originally aired on September 4, 2014.