From what we can tell (mostly thanks to Wikipedia), the trend of combining fried chicken with waffles originated at the Wells Supper Club in Harlem around 1938 when late-night patrons couldn't decide if they wanted dinner or breakfast. The dish then spread to (or created) restaurant chains like Roscoe's House of Chicken and Waffles and Gladys Knight and Ron Winan's Chicken and Waffles.
Despite it's apparent popularity, we still have trouble imagining how this pair would, well, pair. Sweet buttermilk waffles drizzled in syrup alongside tender deep-fried chicken? We like both things separately, but eating them together doesn't really appeal.
Then again, maybe it's not so far-fetched if you consider the fact that biscuits smeared with honey is another classic accompaniment to fried chicken. Biscuits or waffles, who's to quibble?
In case you want to try it at home...
Are you a fan of chicken and waffles?