We Do Not Belong Together / Move On / Sunday, Sunday in the Park with George (I love the original, but the newest cast and recording with Annaleigh and Jake are definitive and revelatory. These songs will never not make me feel something. Annaleigh's delivery gives me chills).
Words Fail / So Big, So Small, Dear Evan Hansen (First time I saw this in the theatre I broke down. Second time, I broke down. Something about the whole end sequence starting with Words Fail to the bow is transporting and utterly heartbreaking).
What Would I Do, Falsettos ("We're just gonna skip that stage". Ugh, gets me every time).
It's Quiet Uptown / Who Lives, Who Dies, Who Tells Your Story, Hamilton (One of the most haunting finale songs, equally uplifting and crushing. When Eliza took her final gasp in the theatre, I got immense chills).
Flying Away (Finale), Fun Home (So beautiful, and the last "I can see all of Pennsylvania" with Beth closing out the play was a gorgeously touching ending).
Bonus:
Pierre & Natasha / The Great Comet of 1812, Natasha, Pierre & the Great Comet of 1812 (Doesn't have as much power on the recording, but is still great. In the theatre however, with the final light glowing, was beautiful and tragic at once).
For Now, Avenue Q (I know this isn't a sad song but it still gets me every time. I'm still not sure why, I think it's because I always listen to it while sad.....)