As for Bob, the only way he'll stop being a smug lolcow is if he gets thrust into an environment where he's at the mercy of Nature. A serious illness that puts him in a hospital bed over the long term might do it, as he realizes that all of the CONSOOMABLES he loves so well can do nothing to save him from his fate. There are people who reject worldly pleasures and adopt religion under such circumstances. The only other thing that might unsmuggify Bob is him being forced into a post-apocalyptic primitive environment. No modern conveniences, nothing to consoom. Just Bob running around the desert as marauders in tricked out dune buggies chase his fat ass down to either turn him into dinner or into some kind of hood ornament/sex toy.
Now I'm not saying that I'd like something serious to happen to Bob (as far as I'm concerned, I'd rather he experience
Prince Humperdinck's Fate: a long life all alone with his cowardice,) I'm just saying that Bob is unlikely to not
ever be a lolcow, unless something happens that's so serious in nature, that
none of us would care whether anyone else is a lolcow or not.)