Chris
Wimpy
Brutus
Olive Oyl
Popeye

is the correct order, given various reasonable assumptions about some murky variables. Chris attacks someone for no reason. Wimpy refuses to help under any circumstances. Brutus offers to help only under what we assume are unreasonable terms. Olive Oyl barely does anything wrong, but she does effectively reward Brutus' presumably unethical behaviour. Popeye does nothing wrong at all; he just chooses not to be in a relationship, which is his right, however stupid his reason.

How is the fact that this is Lord-motherfucking-British asking the question not remarked upon?

Popeye
Olive
Brutus
Wimpy
Chris

Popeye's the sole reason these shenanigans even got started. Everyone else is a victim of their own weakness, exposed by Popeye's cavalier existence. Olive Oil is co-dependent and is #2 because she posed the question to the rest of them. They were just minding their own business until she came along (thanks to Popeye). Brutus, an opportunist, took advantage of Olive Oil for selfish, but natural reasons. However he nearly trades spaces with Popeye for #1 for inexplicably wanting to bone Olive. Wimpy's sort of a puss, let's be real. Inaction is the same as action, but at least he didn't get all Brutus with Olive, and only offer conditional help in the form of really garbage sex. Chris, although being named Chris (bad outside this context), beat up Popeye, who's the worst on this list, so Chris is #5 in this scenario.

Brutus
Wimpy
Olive
Chris
Popeye

Brutus- Because he's extorting sex from Olive, effectively raping her.
Wimpy- Because he knows what Brutus has planned, and can stop it but does nothing.
Olive- She should have trust that Popeye (a sailor man) can get a boat to come to her. She betrays him by not trusting him.
Chris- Jumps to violence rather than trying to solve the problem peacefully.
Popeye- He should have gone to see Olive before she sold herself, or broken off the relationship before it got to that point.

Moving this video to FlowersInHisHair's personal queue. It failed to receive enough votes to get sifted up to the front page within 2 days.

Chris - assaults somebody for no reason in a situation he's not even involved in
Wimpy - rather than helping someone and taking a stand against an arrogant dick, took the easy way out and refused to get involved
Brutus - showed questionable morals by offering a ride for sex, but Olive was free to refuse the deal so it's not comparable to sexual assault
Popeye - Reacted predictably

Don't know where to put Olive on this list. It depends on her own views about sex outside a committed relationship and any understanding she had with Popeye.