"Oh, hey, you won't believe this bro but basically this young eligible bachelorette waltzed into your castle and offered to stay here as a prisoner forever just as it looked like you'd never break the spell! I MEAN, WHAT ARE THE CHANCES?"

Adam and Aladdin are the luckiest I guess because Adam's chance to break the spell came so unexpectedly when the hope was almost gone and when it was impossible to suggest that this girl would even fall for him. Aladdin is also lucky because he doesn't have to live on a sctreen anymore. Well, and Flynn maybe.

Aladdin is a close second.
Ferdinand would have found another princess eventually without Snow
Charming would probably not have gotten married for a while if Cindy wasn't there to razzle dazzle him at the ball
Phillip's life wouldn't have been THAT bad if he never met Aurora and never woke her up. I guess he got lucky that the fairies heard everything and saved him.
Eric was pretty damn lucky Ariel saved him from the storm
Aladdin was so lucky with the lamp. He got lucky so many times with the genie and the freebies
Adam was the luckiest because Belle came just in time and she told him that she loved him like 5 seconds before the last petal fell. He would have been a beast forever if she hadn't come
I guess Shang was lucky Mulan saved him from the avalanche
John Smith really wasn't that lucky....
Naveen was pretty lucky that Tiana saved him from being a frog forever
Flynn is lucky he kept getting away from the thugs and was rescued from like execution.

He was lucky Ariel saved him from that ship! Also he's lucky he got the prettiest, coolest mermaid ever to fall for him. Adam & Aladdin are also pretty darn lucky.

and flynn

Don't take me wrong, but he was so shallow,with no connection with nature and he didn't understand the meaning of life. But then Pocahontas came and he became a new person, he lived!!!!
He told it after all in his own song "If I never knew you". And anyway, I think everyone exists but not everyone really LIVES.He was wounded,almost died,he was seperated from his love.. But John Smith finally lived (I mean real life,not existence)!!!I believe if you're not to live,then there's no point to exist. That's why I didn't pick Eric or Adam....
but i think most of them.
eric-he was saved by ariel
beast-he turned into human again
naveen-he was a shallow man,he turned into a nice guy
flyn and aladdin-they were thieves,they turned into royal

Meh, I guess I am too sensitive and don't see things the way you do.

John Smith didn't seem all that Iucky to me...

Aladdin would be an option, but it wasn't luck, it was his own merit: he's the diamond on the rough. He wasn't selected out of pure chance.