February 13, 2026 • 16 mins
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.
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Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Request Left show is a production of iHeart Radio. Okay,
you guys, as promised, I've shared my thoughts about ten
(00:25):
love songs that are perfect for any Valentine's mix, 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. But
if anything, I can say that heartbreak and soul music
(00:48):
absolutely no strangers to each other. And that said, I
would like to share some songs that I think if
you want to sulk and kind of you know, I'm
very familiar with the comfort of sadness. Sometimes feeling sad
(01:11):
makes us feel good, which I don't recommend because that
can lead to depression. So however, I'm the master of curations,
so I will give you ten songs that will kind
of put you in the mood to cry if you
feel like you need to do so. I'll say the
number one song, probably the most mournful song that I
know in jazz, is Donald Bird's song called Christo Red Dentor,
(01:37):
And oftentimes this song gets chosen almost as a foreshadowing,
like some bad's about to happen. I recall Spike Lee
using this and be Malcolm CH's movie. First of all,
it's mostly it's a vocal choir really doing the duties
(01:58):
of the arrangements. There's a you know, it's a jazz
song with piano upright, bass, very light brush drums and
of course Donald Bird on a trumpet. But it's very
mournful sounding, very sad sounding. I can't even lie to you.
I can't even say that this z apropos for a funeral.
(02:22):
I put a playlist together for my brother Michael Archer D'Angelo,
and this was my opening song. But even when I
put it on like it brought the mood down and
kind of the funeral directors like, do you have anything
more celebratory? Like, you know, I know we're sad here,
but you know here, I was like, yeah, okay, I
went too far. So but I will say that if
(02:45):
crying is your goal, loneliness is your goal, you got
to start with Cristo red Dentor by Donald Bird. It's
on his album A New Perspective Number two. Longtime QLs
guests formerly known as Terrence Trindarby, now going by the
(03:08):
name of Sonata Matrea. He has a song called Seasons
I'll be honest with you. Chris Rock put me onto this.
He's like, yo, go to Symphony or Damn, which was
his third album after Neither Fish nor Flesh, and I
(03:28):
believe Symphony or Damn might have come out in ninety
two ninety three. There's a song called Seasons, and you know,
during that time period, I was going through a breakup.
And the song actually kind of has a theory about
(03:48):
the cycle of love, which is basically like, sometimes you
just love is a seasonal thing. Like I know, we
are taught to think that, you know, this is the
last person that you will be with, you are stuck
with this person for life. But sometimes love is seasonal sometimes,
you know, depending on if you're a person that believes
in astrology in the stars, Like sometimes it's it's a
(04:10):
ten year thing. Sometimes it's a twenty year thing. Look
bands the Beatles, love was a seven year thing. The
roots are in our thirty eighth year of whatever it
is that we call this thing. So but the song
is actually execute it very well. It's called Seasons, and
(04:36):
it deals with the realization of a relationship is over
and hey, we had a good run, but love has seasons,
all right. My third song in the heartbreak choice is
by the one and only Don Blackman. Of course, Holding
You Loving You is a fan favorite, especially if you're
(05:00):
Dylla slim Village head for samples. However, since You've Been
Away So Long is another song that's just as classic
as Holding You Loving You, less problematic if you know
what I mean. Wink anyway, Yeah, since You've been in
Way so long just talks about morning of a relationship,
(05:26):
but it could also apply to just not seeing someone
for a long time. You don't necessarily have to break up, So,
like smart songwriters know not to add too much information,
Earth Wind and Fire was wise and very early to
the game of tacking pronouns out so that their song
could apply to anyone. And sometimes as a songwriter, if
(05:51):
you present your lyrics or your course in a way
that leaves the door open. You know, since You've been
in a way so long could be about a breakup
or could it just be about a long road trip
and missing someone and I'm coming back? So the song
applies to both, so I highly recommend it. My fourth
song is a Stevie Wonder composition done with his first wife,
(06:17):
Sorita Wright, former receptionist at Motown that he heard singings
like hey Yould singing, She's like, hey, I song right too.
Sarita pinned some of his greatest lyrics. I believe that
in Stevie world, like music is his main thing, like
lyrics are. I've seen and heard examples of him writing
(06:40):
his songs, but you know he loves to collaborate with people.
And Serta I think has written like just a line
share of some of his greatest songs that we love.
So her pen game is a match. And she has
a song that she did on her second album called
Stevie Wonder per Serrita, and it's called because We Ended
(07:03):
as Lovers, very sad song. It starts with rain and
she and Stevie also use the background choir kind of
as a mournful kind of color that Donald Bird used
for Crystal Redentor. And because We Ended as Lovers is
(07:25):
basically a plea to like, hey, even though we broke up, like,
let's not totally be out of each other's lives. I
believe in amicable breakups. If you break up with someone,
I think you need a year off before you contact
that person, and then you re enter their lives once
the smoke is cleared. I think after a year you
can be friends with your person. So also to note
(07:50):
that Michael Simbello, if you're a fan of flash Dance
and you love the song Maniac, many don't know that
Michael Simbello was one of Stevie Wonder's greatest disciples, Like
he was in Wonder Love his band for the longest
and co wrote with Stevie A Loott. So this is
one of those songs as well that he's involved with.
(08:11):
I'll make it quasi contemporary. In bringing up Mayor Harthorne,
not enough has been said about Mayor's his production methods,
his tactics, like he'll like he really nails the happy
medium between something that's new and something that's classic. And
(08:33):
I gotta say that kind of Mayor's take on a
Delphonics kind of slow jam. And this song is called
a Strange Arrangement, which is the title track. It's just
a gorgeous, gorgeous, gorgeous melody and arrangement. I love it
so much that yes, it's about a breakup. It's about
(08:55):
someone that's realizing, oh this is over. He's like realizing
it in real time. That Dan, I guess, is the
end of the road for us, and so a strange
arrangement by Mayor Harthorne is number five. Number six. Another
unsung hero Betty Davis. Betty Davis is an artist, singer, songwriter, producer,
(09:21):
first Black woman to produce her own music to get
a credit for it, which you know her work that
she released in the early seventies, women weren't really ever
given agency to have their own ideas, and especially for
black women, and Betty's fight for her artistry is probably
(09:42):
the thing that we know most about her. She also
kind of did everything ten years before anyone else. So
she was Prince before Prince, and she was Madonna before Madonna.
She had entered Miles Davis life when she was just
turning nineteen twenty, and just her youthfulness and her perspective
(10:09):
on the world kind of had an effect on Miles
Davis and this is why he created A Bitches Brute.
There is a song on a compilation called Is It
Love or Desire? And this song is just It is
called when Romance Says Goodbye. It's a very quiet song,
(10:31):
very haunting, but also kind of ry and full of humor.
I love the way that she overenunciates the word lovers.
She calls it live os like it's almost like five
syllables a live oz love oz Betty Davis when Romance
(10:53):
says goodbye. Next up on the heartbreak list, of course,
is a song called I'm Alone and in prom to
improv song by Bobby McFerrin, now known as father of
Taylor McFerrin and Javon McFerrin, of course Madison McFerrin. But
it's just a display of his mastery of handling multiple
(11:18):
duties at once as lead singer, as bass player, as
multiple singers, just as a one man show, and showing
his humor as well. It's a song just talking about
being alone, which sometimes isn't a bad thing, but he
(11:41):
can't help but put humor in his music. So this
is one of those songs in which it is kind
of fun to hear the audience laughing at his punchlines
because clearly he's making stuff up at the last minute.
So I'm Alone by Bobby McFerrin, number eight, very new.
If you know me and you followed me on the socials,
you know that my love for the group Salt is strong,
(12:04):
and the brightest star in that ensemble is, of course
Cleo Soul and if you go to a Rose in
the Dark album there it is man, you got to
hear the song called I Love You, which could be misleading.
Of course I look at it and be like, oh,
it's a love song, and she's basically saying that I've
(12:25):
heard everything coming out of your mouth except for the
term I love you. So this is a good example
of how to communicate what needs aren't getting met in
your relationship. So it's not necessarily a breakup. Oftentimes relationships
could go to dark emotional territory, and we often panic
(12:46):
because we don't know how to communicate with our significant other.
And sometimes you need a song to help nudge you
to say the words. So I would say that I
Love You by Cleo soul Is that songs at number
eight number nine is a long time favorite. If you
were attendee or if you're on YouTube and you've seen
(13:08):
a Brothers in Arms performance by me and my brother D'Angelo,
I will say that we are You know that we're
very familiar and we know our way around an Ohio
Players song, and I will say that for this song
it is basically our Love has Died by the Ohio Players.
(13:31):
This is on their nineteen seventy two Pleasure album Pleasure,
and it's kind of it's a rather defensive song because
if you know the vocal stylings of Leroy sugar Foot Vonnor,
you know kind of his his baritone growl ah girl
(13:55):
like he whenever it's time for the breakup song, especially
if it's slow, it's time for Sugarfoot to come to
the forefront. Of course I Want to Be Free as
his most famous song. But if you listen to Our
Love Has Diet, I mean, the title in itself has
(14:16):
pretty much tells you everything you need to know about
the song. Yeah, our Love has Died by the Ohio
Players and our final song in this sort of my
top ten go to's for breakup songs and for heartbreak songs.
Les mc cann's has an album called Layers and the
title loan says it all and it's called Sometimes I Cry.
(14:41):
I highly recommend this. One of the one of the
biggest breakthroughs that I've had in therapy was sort of
the shock look or my therapist's face when you know,
I was counting on two hands, like the amount of
times I've cried in a decade. She's like, wait, you've
you've only ride maybe twelve times and ten years, And
(15:03):
I was like, yeah, average maybe one and a half
times a year. You know, her jaw dropping on the floor. Look,
it was I was raised. I was taught we weren't
supposed to cry. Now I cry the drop of the
hat because we're not going to survive if we don't
express our emotions. You don't want it to sit down.
(15:23):
But sometimes I cry. Also has a really gorgeous apar loop.
And if you're a hip hop head, I will say
that slick Ricks behind Bars produced by Warren G. It's
so weird that Warren G produced that song. And I
will say that that song has like no trace of
(15:48):
the G funk that I'm accustomed to coming from Warren G.
So when the behind Bars song first came out, that remix,
the Warren G remix of it, of course I was
and like, you know, some gangster and it was far
from that. It was it almost felt like a tripod
quest produced it. Like that's how weird it talented to
(16:10):
hear like I kept checking, like, wait, Warren G did this?
So but the sample of course comes from uh sometimes
I cry by Les mccannon and so those are my
ten heartbreak songs, and don't don't get too comfortable in
heartbreak like it's it's good to get your emotions out,
but don't live there. All right, Well, that's my take
(16:35):
on Valentine's songs you should check out basically,
Request Left show is a production of iHeart Radio. Okay,
you guys, as promised, I've shared my thoughts about ten
(00:25):
love songs that are perfect for any Valentine's mix, 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. But
if anything, I can say that heartbreak and soul music
(00:48):
absolutely no strangers to each other. And that said, I
would like to share some songs that I think if
you want to sulk and kind of you know, I'm
very familiar with the comfort of sadness. Sometimes feeling sad
(01:11):
makes us feel good, which I don't recommend because that
can lead to depression. So however, I'm the master of curations,
so I will give you ten songs that will kind
of put you in the mood to cry if you
feel like you need to do so. I'll say the
number one song, probably the most mournful song that I
know in jazz, is Donald Bird's song called Christo Red Dentor,
(01:37):
And oftentimes this song gets chosen almost as a foreshadowing,
like some bad's about to happen. I recall Spike Lee
using this and be Malcolm CH's movie. First of all,
it's mostly it's a vocal choir really doing the duties
(01:58):
of the arrangements. There's a you know, it's a jazz
song with piano upright, bass, very light brush drums and
of course Donald Bird on a trumpet. But it's very
mournful sounding, very sad sounding. I can't even lie to you.
I can't even say that this z apropos for a funeral.
(02:22):
I put a playlist together for my brother Michael Archer D'Angelo,
and this was my opening song. But even when I
put it on like it brought the mood down and
kind of the funeral directors like, do you have anything
more celebratory? Like, you know, I know we're sad here,
but you know here, I was like, yeah, okay, I
went too far. So but I will say that if
(02:45):
crying is your goal, loneliness is your goal, you got
to start with Cristo red Dentor by Donald Bird. It's
on his album A New Perspective Number two. Longtime QLs
guests formerly known as Terrence Trindarby, now going by the
(03:08):
name of Sonata Matrea. He has a song called Seasons
I'll be honest with you. Chris Rock put me onto this.
He's like, yo, go to Symphony or Damn, which was
his third album after Neither Fish nor Flesh, and I
(03:28):
believe Symphony or Damn might have come out in ninety
two ninety three. There's a song called Seasons, and you know,
during that time period, I was going through a breakup.
And the song actually kind of has a theory about
(03:48):
the cycle of love, which is basically like, sometimes you
just love is a seasonal thing. Like I know, we
are taught to think that, you know, this is the
last person that you will be with, you are stuck
with this person for life. But sometimes love is seasonal sometimes,
you know, depending on if you're a person that believes
in astrology in the stars, Like sometimes it's it's a
(04:10):
ten year thing. Sometimes it's a twenty year thing. Look
bands the Beatles, love was a seven year thing. The
roots are in our thirty eighth year of whatever it
is that we call this thing. So but the song
is actually execute it very well. It's called Seasons, and
(04:36):
it deals with the realization of a relationship is over
and hey, we had a good run, but love has seasons,
all right. My third song in the heartbreak choice is
by the one and only Don Blackman. Of course, Holding
You Loving You is a fan favorite, especially if you're
(05:00):
Dylla slim Village head for samples. However, since You've Been
Away So Long is another song that's just as classic
as Holding You Loving You, less problematic if you know
what I mean. Wink anyway, Yeah, since You've been in
Way so long just talks about morning of a relationship,
(05:26):
but it could also apply to just not seeing someone
for a long time. You don't necessarily have to break up, So,
like smart songwriters know not to add too much information,
Earth Wind and Fire was wise and very early to
the game of tacking pronouns out so that their song
could apply to anyone. And sometimes as a songwriter, if
(05:51):
you present your lyrics or your course in a way
that leaves the door open. You know, since You've been
in a way so long could be about a breakup
or could it just be about a long road trip
and missing someone and I'm coming back? So the song
applies to both, so I highly recommend it. My fourth
song is a Stevie Wonder composition done with his first wife,
(06:17):
Sorita Wright, former receptionist at Motown that he heard singings
like hey Yould singing, She's like, hey, I song right too.
Sarita pinned some of his greatest lyrics. I believe that
in Stevie world, like music is his main thing, like
lyrics are. I've seen and heard examples of him writing
(06:40):
his songs, but you know he loves to collaborate with people.
And Serta I think has written like just a line
share of some of his greatest songs that we love.
So her pen game is a match. And she has
a song that she did on her second album called
Stevie Wonder per Serrita, and it's called because We Ended
(07:03):
as Lovers, very sad song. It starts with rain and
she and Stevie also use the background choir kind of
as a mournful kind of color that Donald Bird used
for Crystal Redentor. And because We Ended as Lovers is
(07:25):
basically a plea to like, hey, even though we broke up, like,
let's not totally be out of each other's lives. I
believe in amicable breakups. If you break up with someone,
I think you need a year off before you contact
that person, and then you re enter their lives once
the smoke is cleared. I think after a year you
can be friends with your person. So also to note
(07:50):
that Michael Simbello, if you're a fan of flash Dance
and you love the song Maniac, many don't know that
Michael Simbello was one of Stevie Wonder's greatest disciples, Like
he was in Wonder Love his band for the longest
and co wrote with Stevie A Loott. So this is
one of those songs as well that he's involved with.
(08:11):
I'll make it quasi contemporary. In bringing up Mayor Harthorne,
not enough has been said about Mayor's his production methods,
his tactics, like he'll like he really nails the happy
medium between something that's new and something that's classic. And
(08:33):
I gotta say that kind of Mayor's take on a
Delphonics kind of slow jam. And this song is called
a Strange Arrangement, which is the title track. It's just
a gorgeous, gorgeous, gorgeous melody and arrangement. I love it
so much that yes, it's about a breakup. It's about
(08:55):
someone that's realizing, oh this is over. He's like realizing
it in real time. That Dan, I guess, is the
end of the road for us, and so a strange
arrangement by Mayor Harthorne is number five. Number six. Another
unsung hero Betty Davis. Betty Davis is an artist, singer, songwriter, producer,
(09:21):
first Black woman to produce her own music to get
a credit for it, which you know her work that
she released in the early seventies, women weren't really ever
given agency to have their own ideas, and especially for
black women, and Betty's fight for her artistry is probably
(09:42):
the thing that we know most about her. She also
kind of did everything ten years before anyone else. So
she was Prince before Prince, and she was Madonna before Madonna.
She had entered Miles Davis life when she was just
turning nineteen twenty, and just her youthfulness and her perspective
(10:09):
on the world kind of had an effect on Miles
Davis and this is why he created A Bitches Brute.
There is a song on a compilation called Is It
Love or Desire? And this song is just It is
called when Romance Says Goodbye. It's a very quiet song,
(10:31):
very haunting, but also kind of ry and full of humor.
I love the way that she overenunciates the word lovers.
She calls it live os like it's almost like five
syllables a live oz love oz Betty Davis when Romance
(10:53):
says goodbye. Next up on the heartbreak list, of course,
is a song called I'm Alone and in prom to
improv song by Bobby McFerrin, now known as father of
Taylor McFerrin and Javon McFerrin, of course Madison McFerrin. But
it's just a display of his mastery of handling multiple
(11:18):
duties at once as lead singer, as bass player, as
multiple singers, just as a one man show, and showing
his humor as well. It's a song just talking about
being alone, which sometimes isn't a bad thing, but he
(11:41):
can't help but put humor in his music. So this
is one of those songs in which it is kind
of fun to hear the audience laughing at his punchlines
because clearly he's making stuff up at the last minute.
So I'm Alone by Bobby McFerrin, number eight, very new.
If you know me and you followed me on the socials,
you know that my love for the group Salt is strong,
(12:04):
and the brightest star in that ensemble is, of course
Cleo Soul and if you go to a Rose in
the Dark album there it is man, you got to
hear the song called I Love You, which could be misleading.
Of course I look at it and be like, oh,
it's a love song, and she's basically saying that I've
(12:25):
heard everything coming out of your mouth except for the
term I love you. So this is a good example
of how to communicate what needs aren't getting met in
your relationship. So it's not necessarily a breakup. Oftentimes relationships
could go to dark emotional territory, and we often panic
(12:46):
because we don't know how to communicate with our significant other.
And sometimes you need a song to help nudge you
to say the words. So I would say that I
Love You by Cleo soul Is that songs at number
eight number nine is a long time favorite. If you
were attendee or if you're on YouTube and you've seen
(13:08):
a Brothers in Arms performance by me and my brother D'Angelo,
I will say that we are You know that we're
very familiar and we know our way around an Ohio
Players song, and I will say that for this song
it is basically our Love has Died by the Ohio Players.
(13:31):
This is on their nineteen seventy two Pleasure album Pleasure,
and it's kind of it's a rather defensive song because
if you know the vocal stylings of Leroy sugar Foot Vonnor,
you know kind of his his baritone growl ah girl
(13:55):
like he whenever it's time for the breakup song, especially
if it's slow, it's time for Sugarfoot to come to
the forefront. Of course I Want to Be Free as
his most famous song. But if you listen to Our
Love Has Diet, I mean, the title in itself has
(14:16):
pretty much tells you everything you need to know about
the song. Yeah, our Love has Died by the Ohio
Players and our final song in this sort of my
top ten go to's for breakup songs and for heartbreak songs.
Les mc cann's has an album called Layers and the
title loan says it all and it's called Sometimes I Cry.
(14:41):
I highly recommend this. One of the one of the
biggest breakthroughs that I've had in therapy was sort of
the shock look or my therapist's face when you know,
I was counting on two hands, like the amount of
times I've cried in a decade. She's like, wait, you've
you've only ride maybe twelve times and ten years, And
(15:03):
I was like, yeah, average maybe one and a half
times a year. You know, her jaw dropping on the floor. Look,
it was I was raised. I was taught we weren't
supposed to cry. Now I cry the drop of the
hat because we're not going to survive if we don't
express our emotions. You don't want it to sit down.
(15:23):
But sometimes I cry. Also has a really gorgeous apar loop.
And if you're a hip hop head, I will say
that slick Ricks behind Bars produced by Warren G. It's
so weird that Warren G produced that song. And I
will say that that song has like no trace of
(15:48):
the G funk that I'm accustomed to coming from Warren G.
So when the behind Bars song first came out, that remix,
the Warren G remix of it, of course I was
and like, you know, some gangster and it was far
from that. It was it almost felt like a tripod
quest produced it. Like that's how weird it talented to
(16:10):
hear like I kept checking, like, wait, Warren G did this?
So but the sample of course comes from uh sometimes
I cry by Les mccannon and so those are my
ten heartbreak songs, and don't don't get too comfortable in
heartbreak like it's it's good to get your emotions out,
but don't live there. All right, Well, that's my take
(16:35):
on Valentine's songs you should check out basically,
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