miserable/ugly as sin

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(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

*ugly as sin

Cliché extremely ugly. (*Also: as ~.) Why would anyone want to buy that dress? It's as ugly as sin! Harold is ugly as sin, but his personality is very charming.
See also: sin, ugly

ugly as sin

Physically or morally hideous, as in I can't think why she likes that dog; it's ugly as sin. This simile, first recorded in 1801, replaced the earlier ugly as the devil.
See also: sin, ugly

ugly as sin

If someone or something is as ugly as sin, they are very ugly. Even his kids were ugly as sin.
See also: sin, ugly

(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

ugly as sin

verb
See also: sin, ugly

ugly as sin

Hideous, either physically or spiritually. This simile appears to have replaced the earlier ugly as the devil, mentioned by Daniel Defoe in his History of the Devil (1726). The first appearance in print was in Maria Edgeworth’s Popular Tales of 1804: “Why, she is ugly as sin!”
See also: sin, ugly
References in periodicals archive ?
Keano star of Muppet Show ROY KEANE has found the antidote to the dreaded selfie - appearing as miserable as sin when someone takes one with him.
He looked as miserable as sin having scored the goal but that is his unique style.
It's now day five and counting I'm as miserable as sin To hell with resolutions I don't have the willpower to win!
she has got happier since she got engaged because before she had a face miserable as sin."
assuring us it was the happiest day of his life, he looked as miserable as sin.
They were soaked through and it would have been easy to forgive them for, at the worst, cancelling the whole gala or walking about looking as "miserable as sin".
He was captured on canvas by Charlie Wells, Clare Shenstone and Richard Brazier but looks miserable as sin in every picture.
How come they're in the top hotels in the world, with a sexy woman rubbing in sun cream, and no work to do for a month, yet they look as miserable as sin?
In ordinary circumstances, I'd have been miserable as sin.