Dawson Leery after like season 4 of Dawson’s Creek.

He started as a cliched and innocent hopeless romantic with aspirations to be a filmmaker but then at a certain point devolved into a somewhat jealous, bitter, angry, possessive person who also decides to run away from responsibility and commitments when it gets too tough and sometimes blames others. I don’t want this to sound too harsh as I would want to give him the benefit of the doubt and he was a teenager who made mistakes and there are reasons for a lot of his behavior, but I think as a character they kinda dropped the ball with him towards the end.

Jack Bauer on 24.

His defense in the name of national security for his barbaric torture and threatening innocents with violence and death if they didn’t so what he says became tired and a crutch after a while and his bad behavior couldn’t possibly be justified after a while. I was willing to have sympathy for him after loved ones either died or left him, but it doesn’t give him the right to point a gun at an innocent person and tell them he will kill them if they don’t do exactly as he says. He’s also displayed hypocritical behavior when he judges and criticizes people for doing similar things to what he’s done which makes him a little tired and unlikable for me after a while.

Karen Walker on Will & Grace, like The Todd snd Bulldog, was intentionally written that way but was still very unlikable even though I could still kinda understand her behavior to a point when you look deeper and realize why she acts the way she does and she displays great heart sometimes.

Others:

Ross on Friends for the obvious reasons anyone familiar with the show already knows. Rachel to a degree as well, but I think Ross’ list of douchey behavior takes the proverbial cake.

The Todd on Scrubs was a total creep and a perverted human being, but he was intended to be that way and he was only a side character.

The crew on Seinfeld in the latter years especially were largely horrible human beings.

Ryan Howard on The Office was a largely appalling human being, although he looked great in a fedora.

Bob “Bulldog” Briscoe, like The Todd on Scrubs, was a lawsuit waiting to happen on Frasier and a chauvinistic and openly offensive person like him couldn’t exist in real life.