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The Questlove Show

Questlove's Valentine's Day Music Picks - The Heartbreak Edition

The Questlove Show

iHeartPodcasts

Music, Society & Culture

4.62K Ratings

🗓️ 13 February 2026

⏱️ 17 minutes

🧾️ Download transcript

Summary

As Valentine’s weekend arrives, Questlove follows his love-inspired soundtrack with a different kind of selection, one pulled from the side of the crate reserved for heartbreak. He suggests ten songs that sit with loss, loneliness, and love that’s run its course, spanning Jazz and Soul laments from Donald Byrd and Les McCann to more modern reflections by Mayer Hawthorne and Cleo Sol.

Along the way, he shares the stories, anecdotes, and personal reflections that make these records ideal companions for a good cry — and, maybe, a little clarity.

If this year finds you on the hurting or healing end of love, consider this episode your solace.

See omnystudio.com/listener for privacy information.

Transcript

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0:00.0

This is an I-Heart podcast.

0:02.6

Guaranteed Human.

0:04.6

The Questlove show is a production of I-Heart Radio.

0:32.8

Okay, you guys, as promised, I've shared my thoughts about 10 love songs that are perfect for any Valentine's mix.

0:40.3

But I know on the other side of that coin, Valentine's could be a reminder of a love gone wrong. Love gone wrong is a tragic in any person's life.

0:46.3

But if anything, I can say that heartbreak and soul music, absolutely no strangers to each other and that said i would like to share

1:00.7

some songs that i think if you want to sulk and kind of uh you know i'm very familiar with the comfort of sadness. Sometimes feeling sad

1:15.5

makes us feel good, which I don't recommend because that can lead to depression. So, however,

1:21.8

I'm the master of curation, so I will give you 10 songs that will kind of put you in the mood to cry if you feel like you need to do so.

1:30.3

I'll say the number one song, probably the most mournful song that I know in jazz, is Donald Bird's song called Christo Redentor.

1:41.9

And oftentimes, this song gets chosen almost as a foreshadowing, like something bad's about to happen.

1:52.1

I recall Spike Lee using this in the Malcolm X movie. First of all, it's mostly, it's a vocal

2:00.4

choir, really doing the duties of the arrangements.

2:04.7

There's a, you know, it's a jazz song with piano, upright bass, very light brushed drums and chorus Donald Bird on the trumpet, but it's a very mournful sounding, very sad sounding.

2:20.3

I can't even lie to you. I can't even say that this is apropos for a funeral,

2:27.3

I put a playlist together for my brother, Michael Archer, DeAngelo,

2:33.3

and this was my opening song.

2:35.9

But even when I put it on, like, it brought the mood down and kind of the funeral director's like, do you have anything more celebratory?

2:41.5

Like, you know, I know we're sad here, but, you know, I was like, yeah, okay, I went too far.

2:47.3

So, but I will say that if crying is your goal,

2:52.0

uh, loneliness is your goal, you got to start with crystal red dentor by Donald

2:59.6

Bird.

...

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