Now... I’m about to totally overthink this question but here goes... lol
I think for me it comes down to what we mean by “prettiest”...
"My Girl" is sweet, catchy, happy and yea, it is pretty. It’s lovely. It’s also overplayed and I can’t really hear it without sighing... lol
"Since I Lost My Baby" is essentially the sad version of "My Girl"... everything’s bad, sad and pointless ‘cause the girl is gone. But it’s still pretty. Sad but pretty.
I think “pretty” implies something good, something positive... I mean, being “pretty” is a good thing.. it’s a good quality. "My Girl" is an upbeat song, so does it fit the ‘good’ part of being pretty? Yes, but I feel like "Since I Lost My Baby" has such feeling to it, such emotion, such longing... it’s almost... prettier.
Wow, I impressed myself here with this unnecessarily in-depth answer to your question arr&bee
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