Often used by parents to describe their deceased children (when talking about them to news reporters) aged usually in their late teens/early twenties, (and more often than not, gang members) because they cannot think of anything positive to say about them.
Person 2: "Lovable rogue?! He used to steal money from your purse all the time and spend it on weed and booze, ontop of that him and his mates hospitalized a doorman who refused them entry to that nightclub in town just last weekend, how is that loveable?!"
Person 1: "He had a cheeky smile...."
Person 2: "You need to get your head checked..."