5. "Full Color Love Affair" by The Shimmer Kids Underpop Association

Why: A mellow song about the not-so-mellow experience of being dumped for another person. It perfectly captures the beaten-down tone of self-loathing and hatred that accompanies this experience.
Key lyrics: "When I saw you in the library, well then I knew that it was all over, 'cause he was showing you that book by e.e. cummings. And I had on my favorite shirt, but it didn't seem to make a difference 'cause all the poetry in Paris will never hide my shortcomings. And if our paths cross in a little while, if I should see you at a party, maybe you'll apologize...but you'll still be a bitch."

4. "Recommendation" by Mirah

Why: This is a good one for the defiant, I-am-so-getting-over-you-but-I-still-want-you stage of a breakup. It's a brilliantly compact song about things that you can only write down in letters and the agony of an uncertain ending drawn out by tense long-distance correspondence. In the end Mirah decides that she's doing "Fine. Just fine."
Key lyrics: "You drove so far, but now you know how rough it is to let me go. Let me recommend that you think twice, and I always give the best advice."

3. "True Affection" by The Blow

Why: A perfect expression of that painful sense that you're drifting out of each other's leagues. As always, The Blow combines heartfelt vocals with electronic blips to great effect. There's such a sadness to this song in its recognition of how sometimes genuine affection isn't enough.
Key lyrics: "True affection floats. True affection sinks like a stone. I never felt so close. I never felt so all alone."

2. "I Don't Want to Get Over You" by The Magnetic Fields

Why: Perhaps the most miserable and pathetic breakup emotion is the terrible knowledge that you're not ready for the person to leave your life, despite the fact that they're clearly moving on. This one just comes out and says it: I'm not ready for this, I don't want anyone else, I feel like sulking around and smoking clove cigarettes, etc. Stephin Merritt's sad, dead vocals are basically the sound of being dumped.
Key lyrics:" I could make a career of being blue, I could dress in black and read Camus, smoke clove cigarettes and drink vermouth like I was 17. That would be a scream, but I don't want to get over you."

1. "Landslide" by Fleetwood Mac

Why: So this is pretty obvious. It's kind of the go-to song for major life changes, but there's a reason why it's so popular among the depressed and broken-hearted. Stevie Nicks is at once vulnerable, honest, and willing to acknowledge that things have to change, though not without some hesitation. Everything about it is perfect for post-breakup sadness.
Key lyrics: "I've been afraid of changing 'cause I've built my life around you."

Dolly Parton, "I Will Always Love You," c. 1974

I feel like you just don't see this kind of stellar performance on TV anymore, except maybe on Austin City Limits. But in general, TV musical performances are relegated to crappy late-night talk shows or terrible award shows, and they definitely don't have the kind of rockin' special effects you get at the end of this one. I don't know much about the technical aspects of music, but it seems that this might be a pretty tricky song to sing, and yet there's Dolly, hitting every damn note with a downright chilling sincerity. Not to sound like a total coot, but maybe everyone who performed at the VMAs should have been forced to watch this video until they understood the merits of a quality live performance. It is better to have sung and not danced than to never have sung at all. Anyway, this is a near-perfect performance in every way, and for anyone who's only ever heard the Whitney version, it is a must.

Fleetwood Mac, "Rhiannon," c. 1975

This video's got something for everyone: great vocals, great hair, flowing chiffon, and a rad jam session at the end. And this take, like Dolly's, is actually superior to the recorded version of the song. I've said it before and I'll say it again: if I ever come into some money I will hire a full-time staff to maintain this incredible Stevie Nicks hairdo. Seriously, power hour of hair! What the hell? Anyway, she looks pretty coked out, but it doesn't stop her from ripping through this song with an inspiring ferocity.

Rilo Kiley, "My Slumbering Heart," c. 2003

(FF to 3:56 to skip their technical difficulty.)
There was a time in my life, not too long ago, when I traversed the great state of Texas to see Rilo Kiley perform live multiple times in one week. My favorite song of theirs to hear live has always been "My Slumbering Heart," so I was excited to find this high-quality live video. This song is from their 2002 masterwork The Execution of All Things, a staggeringly beautiful album that will always, sadly, live in the shadows of their latter-day sins (I will never forgive them for this new album).

Diego Luna/Gael García Bernal tribute video

So this isn't exactly essential, but it has long been one of my favorite tribute videos. Everything about it is right: the subject (seriously, you need to see Y tu mamá también), the song choice, the scrappy-but-determined editing. It's very good-natured and always gives me hope when the tribute-video world starts to get weird.

And just for good measure...

Jimmy Buffett, "Come Monday," 1974

This is for my parents. I'm not really going to explain anything here. Just enjoy the easy listening and try to forget that you're too cool for Jimmy. And if you can't unclench a little and just enjoy it, at least consider how ahead of the curve he was, music video-wise. That slo-mo fruit-eating sequence is seminal.