miserable

(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.
See also: miserable, sin

(as) ugly as sin

Extremely visually displeasing or unattractive. This old car is all beat up and ugly as sin, but it's still going strong after all these years. I'm sure I looked as ugly as sin by that point, with my makeup smeared all over the place and my hair a total mess.
See also: sin, ugly

make (oneself) miserable

To cause oneself a great amount of stress, anxiety, sadness, etc. I don't understand why she keeps making herself miserable in a job she hates. She's just not interested in you romantically, Jack, so stop making yourself miserable pining over her!
See also: make, miserable

make life miserable for (one)

To cause one to be continually unhappy; to be a great and continuous source of stress for one. For some reason, the new manager seems to have decided to make life miserable for me. Don't worry, we'll make life miserable for them is they refuse to sign the contract.
See also: life, make, miserable
Farlex Dictionary of Idioms.

make life miserable for someone

to give someone misery; to be a great nuisance to someone. This nagging backache is making life miserable for me. I wish you would stop making life miserable for me.
See also: life, make, miserable

make oneself miserable

to do things which cause one to be unhappy. You're just making yourself miserable by trying to do something you aren't qualified to do. I'm not making myself miserable! You're making me miserable.
See also: make, miserable
McGraw-Hill Dictionary of American Idioms and Phrasal Verbs.

(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.
See also: miserable, sin, ugly
Farlex Partner Idioms Dictionary
See also:
  • (as) miserable as sin
  • miserable/ugly as sin
  • fall into sin
  • as sin
  • sin
  • mulligrubs
  • mullygrubs
  • have the mulligrubs
  • have the mullygrubs
  • ugly
References in classic literature
Is not his case utterly miserable? and does not the actual tyrant lead a worse life than he whose life you determined to be the worst?
Moreover, as we were saying before, he grows worse from having power: he becomes and is of necessity more jealous, more faithless, more unjust, more friendless, more impious, than he was at first; he is the purveyor and cherisher of every sort of vice, and the consequence is that he is supremely miserable, and that he makes everybody else as miserable as himself.
Need we hire a herald, or shall I announce, that the son of Ariston (the best) has decided that the best and justest is also the happiest, and that this is he who is the most royal man and king over himself; and that the worst and most unjust man is also the most miserable, and that this is he who being the greatest tyrant of himself is also the greatest tyrant of his State?
And will any one say that he is not a miserable caitiff who remorselessly sells his own divine being to that which is most godless and detestable?
Republic
Nature by making habit omnipotent, and its effects hereditary, has fitted the Fuegian to the climate and the productions of his miserable country.
The Voyage of the Beagle
"Old World!" retorted the trapper, "that is the miserable cry of all the half-starved miscreants that have come into this blessed land, since the days of my boyhood!
and it proves how great He must be, when His miserable creatur's can accomplish such wonders!
"Cruel enough would be the order, that should come from miserable hands like thine!
The Prairie
Nothing occurred to my thought to contradict any of these conclusions, and therefore it rested upon me with the greater force, that it must needs be that God had appointed all this to befall me; that I was brought into this miserable circumstance by His direction, He having the sole power, not of me only, but of everything that happened in the world.
My condition began now to be, though not less miserable as to my way of living, yet much easier to my mind: and my thoughts being directed, by a constant reading the Scripture and praying to God, to things of a higher nature, I had a great deal of comfort within, which till now I knew nothing of; also, my health and strength returned, I bestirred myself to furnish myself with everything that I wanted, and make my way of living as regular as I could.
Robinson Crusoe
If she spoiled everybody who came near her with kindness and compliments--if she begged pardon of all her servants for troubling them to answer the bell--if she apologized to a shopboy who showed her a piece of silk, or made a curtsey to a street- sweeper with a complimentary remark upon the elegant state of his crossing--and she was almost capable of every one of these follies-- the notion that an old acquaintance was miserable was sure to soften her heart; nor would she hear of anybody's being deservedly unhappy.
She carries laudanum with her-- I saw the bottle in her room--such a miserable little room--at a third-rate house, the Elephant, up in the roof at the top of all.
Vanity Fair
Just as I approached the swing-door leading into the hall from the servants' offices, it was violently opened from the other side, and Rosanna Spearman ran by me, with a miserable look of pain in her face, and one of her hands pressed hard over her heart, as if the pang was in that quarter.
"I was knocking the balls about," he said, "and trying to get this miserable business of the Diamond out of my mind.
"I am not in my proper bed," answered the Sergeant, "because I am one of the many people in this miserable world who can't earn their money honestly and easily at the same time.
The Moonstone