What it means
A head case is someone who's a bit all over the place, unhinged, or running on gloriously bad impulses. It can be quite harsh if you mean someone's seriously unstable, but loads of the time it's said half laughing about the mate who keeps making baffling choices for the plot.
Usage examples
"Yer man just swan-dived off the pier in January, roaring laughing. Absolute head case, like. We’re freezing and he’s saying it’s grand."
"Our old PE teacher was a bit of a head-case, he made us run laps in a thunderstorm for fun."
"Anyone who swims in the sea here in January is a proper head-case, lovely though."
"Don't hand Kev the fireworks after three pints, the lad's a total head case."
"She booked a tattoo at half two in the morning after one bad breakup chat. Absolute head case."
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Where it comes from
It comes from older English use of case for a person seen as having a particular condition, especially in medical and psychiatric talk. Head case shows up in the 20th century for someone thought mentally troubled, then drifted into looser everyday slang for a chaotic or wildly unpredictable person.
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