- While the words to "Box of Rain" might sound like gibberish at first, the lyrics become extremely moving when you know that it was written for Phil Lesh's father who was stricken with terminal cancer. Anyone who's lost someone close to them can relate to the song.
- "Morning Dew", especially live, can be very emotionally powerful. There's a reason the band almost always played it near the close of a show when they played it - and they generally only segued into it during shows they felt had been especially strong, meaning that fans considered it a major treat to be present for a performance. As stated on the main page, the song is intended to be a dialogue between the last surviving man and woman on the planet after a nuclear holocaust, and a careful reading of the lyrics suggests they may even be Driven to Suicide at the end (an earlier stanza says, "I can't walk you out in the morning dew, my honey", presumably because it's too dangerous to do so, but the end stanza says "I'll walk you out in the morning dew, my honey / I guess it doesn't matter anyway", which, in conjunction with some of the other earlier stanzas, implies that they got sick of living on a planet with no other people on it and decided to let their surroundings kill them), so it definitely qualifies on several levels.
- "Black Peter" is one of the band's most emotionally wrought songs both lyrically and musically.The people may know but people don't careThat a man could be as poor as meTake a look at poor Peter; he's lying in painNow let's go run and see, run and see
- "Row Jimmy" is also a contender.That's the way it's been in townEver since they tore the jukebox downTwo bit piece don't buy no moreNot so much as it done before
- "Wharf Rat". The narrator meets a blind, destitute old man who's spent much of his life doing prison time for a crime someone else committed. He asks the narrator for money for coffee, but the narrator doesn't have any; however, he listens to the old man's story. Now out of prison, the old man is trying to turn his life around. The old man also worries about whether the woman he loves has been faithful to him. The narrator reassures the old man that she has been, but at the end of the song, the narrator sounds like he has doubts about his own relationship, much as he insists he doesn't.
- "Brokedown Palace" is a particularly wrenching Break Up Song, due in no small part to Hunter's lyrics and the band's harmonies.
- "Peggy-O", their rendition of a traditional Scottish ballad about a tragic romance between a ship's captain and the woman of the title, is both beautiful and heartbreaking.
- Comes a Time, another beautiful, heartbreaking, downtempo ballad, though its lyrics also cause it to double as a Heartwarming Moment. The song is about being at an absolutely miserable point of one's life and being reassured that You Are Better Than You Think You Are, and of The Power of Love.
Tear Jerker / The Grateful Dead