Steve-Dave
Newbie
I like Cloud and Squall equally, to me they're my top two FF characters.
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Since FF8 was my first FF game, and since I love Squall's character development, he is one of my favorite characters. However, Cloud is such a totally amazing/awesome/great character so it is very difficult to choose between the two 

The Cloud we see in Crisis Core is actually very charming. Had they brought this Cloud back in Advent Children, thereby implying that his character had found peace, I may have voted Cloud. 
But those are my reasons for loving Squall! 
I just prefer him, I don't know why. I think it's because while Cloud had something really dramatic and traumatising happen to him which was what dented his personality, Squall's development came from a much simpler, more realistic route. He lost the only family he knew and that affected him badly and throughout the game we get to see him come back to himself. I know he seems very mean, but that's not really who he is, that's the way he deals with his loss, he tries to keep everyone at arms length, never bonding with people and staying alone because he's so afraid of losing people again. It's the kind of thing I've seen in reality which makes it more real and better for me to relate to. I can't empathise with Cloud the same, because his problems come from being experimented on and losing himself and having to go a real long way to bring himself back. It's inspirational and in many ways similar to Squall's, but I can't really understand it the way I can understand Squalls, because it's much less realistic, so I just don't 'get' Cloud like I get Squall. I still think he's awesome though
they both are.
To me, Cloud's story just always had more volume than Squall's "I was an orphan" story.
Seeing as how I really dislike FFVII, and especially Cloud, I'd have to go with Squall. I really found him to be a much more interesting character from a game that is in my opinion leagues better.
You mihht sswell not like any ffs before 7. Regardless how was he more interesting?
They both had different proccesses because both had different personalities and situations. I dont think ff7 is a wreck because it stays true to alot of thing. Only way to hate is hating being in this transition look of the graphics and the materia system. But overall i feel cloud deserves more.I like all of the ones before 7 actually.
I think Squall had more personality from the start and better character development. Overall I found Cloud to be very flat and uninteresting, and though he did develop somewhat, I didn't feel as though his story as as engaging and his changing wasn't quite as deep. Squall to me was a more believable character considering all he faced, and though his development was gradual, it spoke more to me than Cloud's ever did.

Who whines less? Good question...they both lose. Seriously, they're both devoid of a proper personality in place of constant brooding. Cloud complains to Sephiroth about not being allowed his share of happiness, when he wouldn't be happy even if Sephiroth hadn't come along in the first place. He has two attractive girls fawning over him throughout the entire game and what does he do? He just gives us dots. And don't even get me started on Squall's pointless angst. You're in a school that teaches you to use MAGIC and you can wield a weapon that would ordinarily break someone's wrist...yet you act as though you were born deaf, blind, and without ligaments. Many people are quick to antagonize Zidane for being a womanizer, but at least he was freaking happy throughout the majority of the game. He actually had a personality.
So, who wins? Zidane. Zidane wins.