Is it wrong to feel sorry for Gil?

I really like this character but he really needs a turn of luck. It seems like the Simpsons writers took the Lionel Hutz character (who often slept in dumpsters and had a very obvious drinking problem) and tried to come up with something similar in a ‘hopless individual’ type of character.

Some funny Gil quotes

“Oh, why did you bet the company payroll?! Oh, Gil’s in trouble now!” after losing at Roulette

“Hey I was living in that Balloon! And there was a hot plate in there!” Hot plate smashes on ground “Awww I had two payments left on that thing!”

That’s crazy talk. What’s next? Barney clean and sober?

I think the writers saw Glengarry Glen Ross and found Gil there.

And don’t knock his bad luck. If it wasn’t for that he’d have no luck at all.

Wrong? I think it’s absolutely his raison d’etre.

I agree with don’t ask, definitely Shelley Levene from Glengarry Glen Ross.

I feel sort of uncomfortable when ol’ Gil is on. I know I should be laughing, but all I can do is cringe. A bit like the scene where Mr. Burns drills a hole in Hans Moleman’s head (offscreen, natch) to get his lucky charms. Very borderline…

And let’s not forget ol’ Gil, huh? The wolf’s at old Gil’s door.

Poor Gil, walls are for closers.