Just hitting the highlights here! Top three songs that I can think of. And if I missed something, add it in the comments.
“Tu Hi Re” Rahman, Hariharan, Ratnam visuals
“Channa Maraye” Pritam, Arijit, Johar visuals
“Ajeeb Dastan Hai Ye” Shankar-Jaikishan, Lataji, Kishore Sahu visuals
dontcallitbollywood 
I’m going to go with Ajeeb Dastan. Meena Kumari and Raaj and also, Channa Mereya gives me so much secondhand embarrasment. Tu Hi Re for me is less about love-yearning, but more about yearning for another place, another time (like, even if they got what they wanted, they want to live with that somewhere else and not deal with all the difficulties obtaining it would actually bring). Ajeeb Dastan is just earthy enough for it to be about a person.
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Yaaaay, “Ajeeb Dastan” gets a win!!! I know what you mean about Channa, it’s partly Ranbir’s misery and partly Anushka’s discomfort with his misery. While “Ajeeb Dastan” is the same kind of moment, only that time the love object has no idea what is happening, it’s just her pain.
On Mon, Jan 11, 2021 at 5:44 PM dontcallitbollywood wrote:
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Tu Hi Re!! It always gets me and I love Kavita. My runner up is ai dil-e-nadaa.n, which I’ve always thought conveys such sad longing, but I’ve never actually seen the movie. It seems like it though based on this translation I found here: https://mrandmrs55.com/2015/09/28/aye-dil-e-nadaan-lyrics-and-translation-lets-learn-urdu-hindi/
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I love the song Tu hi re, but the picturization was pretty cringe.
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Ajeeb Dastan Hain is an all time favourite for me.
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