(as) miserable as sin
Extremely unhappy, depressed, or wretched. Everyone just stood around looking miserable as sin during the ceremony. I felt as miserable as sin because of the breakup, but I was going to be best man at my brother's wedding, so I had to pick myself up and dust myself off.
(as) miserable/ugly as ˈsin
(spoken) used to emphasize that somebody is very unhappy or ugly: He arrived at the party looking as miserable as sin.Some babies are as ugly as sin at that age.