First of all, it's not a comic until you actually draw something for it! This is a script, and scripts only ever contain half the humour value.
Considering the massive comic potential of Thompson, your comic/script doesn't really seem to draw on anything he does. I like the three stages of his life idea (unliked kid, present, future) but none of the words or scenarios seem much like him.
Suggestion: tie them together, or to that story (which is what Penny Arcade would do, say). Example:
Kid Jack - have him tell one of the other kid's mothers that their son is swearing and so is going to Hell, and her with him.
Present Jack - writing letters. "Dear Mrs. Zelnick, your son persuades kids to murder people..." "Dear Mrs. Levine, your son advocates child murder..." "Dear Mrs. Miyamoto, your son says that murdering turtles is a good thing..."
Future Jack - On a gallows or in a guillotine, surrounded by older women holding placards that read 'Mothers 4 Justice'. "All I said was that your sons are murderers and you're going to Hell!"