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pathetic - Arousing pity, especially through vulnerability or sadness

The condition of the homeless person sleeping by the river was so pathetic that Bill had to give him a dollar.

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diabolical - Extremely evil or cruel; wicked.

The criminal mastermind came up with a diabolical scheme to rob the large jewelry store.

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malevolent - Having a desire to do harm or evil to others.

Samantha brought her 4 year old son Eddie to the therapist, because of the way he expressed malevolent intentions to torture animals.

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dire - (of a situation or event) extremely serious or urgent

Finding survivors under the earthquake's rubble was a dire situation.

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culpable - Deserving to be blamed or considered responsible and guilty for something bad that happened.

The mother felt that her oldest son was more culpable for the messy bedroom than his younger brother, because he should have known better.

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woe - Great sorrow or distress

Young Billy always felt woe at school whenever the bullies would pick on him.

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infamous - Well known for some bad quality or deed

Willie Sutton is infamous for saying that he robbed banks because 'That's where the money is'.

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gruesome - Causing horror, disgust, and shock - usually dealing with death or injury:

When the policeman visited the scene of the murder, the sight was so gruesome that he couldn't help but go outside and throw up.

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no-no - Something that is not allowed or is strongly discouraged.

Wearing jeans to a formal wedding is a big no-no.

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quagmire - A soft boggy area of land that gives way underfoot

After the thunderstorm, the troops had to watch their step to avoid sinking into the quagmire of mud underneath them.

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debacle - A sudden and ignominious failure; a fiasco

Amongst human-led disasters, the sinking of the Titanic is considered a major debacle.

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horrific - Causing extreme fear, shock, or disgust.

The accident was so horrific that witnesses were left trembling.