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!”
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…