The whole point of the mythological trickster is an inhuman being who aids humans by confronting said humans with their own bullshit. The tricksters use their “tricks” to shed light, not just to embarrass someone. They’re not being evil or even mean by their own standards; they just have what TV Tropes would call a “Blue and Orange Morality” (meaning their logic is so completely beyond human logic, it gets downright confusing for us mere mortals). Puck from Shakespeare’s “A Midsummer Night’s Dream” is an excellent example of the classic trickster.
SPN!Gabriel tricked Sam in “Mystery Spot” to point out to him that his dependence on Dean was seriously unhealthy. Gabriel then followed that up in “Changing Channels” to teach them that they both have a role to play, and they have to know what that role IS before they can start breaking the rules. Gabriel was definitely on their side; he wanted to give them the lessons they needed to learn in order to save the world.
And the boys earned Gabe’s respect when they confronted HIM with his family-related bullshit, too. 🙂
(Yes, Gabriel is one of my faves… but I’m a total mythology nerd too.)