A lot of people correct this usage of the expression “I could care less.“ But Mr. Mays’ use of this expression is quite common, and arguably legitimate. I have a theory as to where it arose. I have most often heard this expression used by Jewish people, especially Jewish comedians. The ancestral language of most American Jews is Yiddish, and Yiddish is very similar to German in vocabulary and structure. German, unlike English, has a distinctive subjunctive mood, which expresses that something could be true but isn’t. If one said the equivalent of “I could care less” in the Yiddish subjunctive mood, what one would be saying is something like “ do you think I could care less? I couldn’t.” I think when a Yiddish influenced speaker says “I could care less“, they are reaching for a subjunctive mood that English doesn’t really have. I know no Yiddish, and very little German, so I’m no authority on this. I would appreciate any contradictions or confirmations of this speculation from anyone.