The saddest chord progression ever

See also the happiest chord progression ever.

The short-lived Russian composer Vasily Kalinnikov is best known (to the extent he’s known at all) for this piece of music:

If you listen to this piece at 6:16, there’s a particularly beautiful and tragic chord progression. It’s in the key of E-flat, but I transposed it into C for ease of understanding:

I mentally refer to this progression as the Willie Nelson turnaround, because I first heard it in his classic recording of “I’d Have To Be Crazy”, written by Steven Fromholz. I had the pleasure of performing this tune many times back in my country music days, and it makes a great lullaby for my kids.

The version of the progression in “I’d Have To Be Crazy” uses a different harmonic rhythm, and starts on the I chord instead of vi. Nevertheless, the emotional effect is the same. Willie’s tune is in E, but again, I transposed into C for easier comparison.

Here’s a mashup of Kalinnikov and Willie:

The descending chromatic feeling you get from D7 to Fm to C is related to a timeless blues riff. It features prominently in a Duke Ellington tune called “Way Way Back,” as performed here by Abdullah Ibrahim:

“Way Way Back” is in F, but I’ve transposed the blues riff into C:

The Cdim7 chord has three notes in common with D7 (F-sharp, A, and C). The Dm7b5 chord similarly has three notes in common with Fm (F, A-flat and C). Still, the emotional impact of the blues cliche is very different. The blues is wistful and has an element of pain, but it isn’t exactly sad the way that Kalinnikov and Willie Nelson are. I think of the blues as being more about overcoming or enduring sadness than just expressing it.

The Kalinnikov/Willie Nelson progression is also related to the “Beatles cadence,” technically a combination major/minor plagal cadence. You can hear it at around 1:00 in “If I Fell,” in the bridge.

This tune is in D, but I’m once again putting it into C for discussion purposes. In the line “but I couldn’t stand the pain,” the word “pain” lands on F, the major IV chord. In the next line, “and I would be sad,” the word “I” lands on Fm, the minor iv chord.

Another close relative of the Kalinnikov/Willie Nelson progression is the one that opens “Can’t Take My Eyes Off Of You” by Frankie Valli.

Here it is in C:

Here we have the same V/V chord as in the saddest progression, but it goes to the IV chord, not the iv. There’s the chromatic descent from #4^ to 4^, but rather than having 6^ fall to b6^, it just stays on 6^. Wistful, maybe, but definitely not sad. The Beatles and Frankie Valli cadences are effective, but they’re tamer and less chromatic than the Kalinnikov/Willie Nelson chords. Why is the Kalinnikov/Willie Nelson turnaround so sad? And why is it so much more hip than the Beatles cadence? I think it’s because of the way it defies your expectations.

Here’s how D7 is supposed to work in the key of C: it temporarily puts you in the key of G. The most conventional (boring) chord to follow D7 is G7, followed by C.

Let’s think of this in terms of scales. In C major, the scale implied by D7 is D Mixolydian, which contains the same pitches as C Lydian, the brightest of all the diatonic modes. Landing on the G7 chord puts us back in C major. There’s a bit of tension from the F rising up to F-sharp and then falling back to F, but basically, all is sweetness and light.

This is not what happens in the Kalinnikov/Willie Nelson progression. Instead of trotting obediently around the circle of fifths like you expect, the D7 unexpectedly resolves to F minor instead. This surprising chord implies F Dorian, alternatively known as C natural minor. So you go from the bright C Lydian sound (C, D, E, F-sharp, G, A, B) to the much darker C natural minor sound (C, D, E-flat, F, G, A-flat, B-flat.) Instead of moving from the brightest scale to the second brightest, you have just moved to a decidedly dark place. Even the voice leading is depressing: the F-sharp and A in the D7 chord slump dejectedly down to F and A-flat in the F minor chord. (The Beatles cadence is weaker because it doesn’t have the lift up to F-sharp before the descent into minor land.) Sadness is that much sadder if you were expecting happiness.