Oscar is a "loser" but Bobby isn't??

That makes no sense!

Bobby is single, not married, no kids, lives at home, babied by Suga Mama, no stable job that I know of.

Oscar is at least married, has kids, his own place, etc. sure selling Proud snacks is a shitty "job", but to me he's doing better than his brother.

What has Bobby done with his life that makes his better than Oscar??