YOU SAID:
He is a hoot and a half
INTO JAPANESE
彼はひどくて半分だ
BACK INTO ENGLISH
He is terrible half
INTO JAPANESE
彼はひどい半分です
BACK INTO ENGLISH
He is awful half
INTO JAPANESE
彼はひどい半分です
BACK INTO ENGLISH
He is awful half
That didn't even make that much sense in English.