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September 12, 2025 • 27 mins

On this episode of The Deepest Cut, Greg LaFollette shares the story behind Psalm 88 (Darkness is my Closest Friend)—a hauntingly honest song born from a season of deep pain. Rather than rushing toward resolution, Greg explores what it means to remain in lament, offering worship for those still in the valley. It’s a moving conversation about faith in the dark, the power of honest prayer, and creating space for sorrow in our spiritual lives.

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S1 (00:01):
Welcome to the Deepest Cut, a podcast about the movement
from painful experiences to meaningful music. I'm your host, Matt Conner.
We've all heard the story wrapped up with a bow.

(00:22):
The heartbreak followed by healing the darkness quickly chased away
by the light. But what if a song or a
story ends in the valley? Like, what if it stays there?
There's always room and reason for hope, obviously. But sometimes
I think we're a bit too quick to move beyond
the doubt and despair. Sometimes such seasons stay with us

(00:43):
or us with them, and company is needed in those
moments as well. That's the reason why Greg LaFollette wanted
to make sure and highlight the prayer uttered in Psalm 88. Now,
even if you're not sure you've heard Greg's work, I'm
actually positive that you have. Not only has Greg offered
up beautiful resources for the church over the years, which,

(01:06):
by the way, includes a worship series for kids. He's
also played with and produced for many, many other artists,
from Sandra McCracken and Sarah Groves to Andrew Peterson and
all sons and daughters. On this episode of The Deepest Cut,
Greg chose to discuss his song Psalm 88, which is

(01:26):
subtitled Darkness is My Closest Friend. It's a track written
from the midst of a painful season, and as he details,
he wanted to craft something for those still in the
thick of the pain, offering worship that doesn't rush to resolve,
but instead lingers in lament. It's heavy. It's also holy.

(01:47):
And it's an honest look at what it means to
trust God in the dark. Here's my conversation with Greg
LaFollette here on The Deepest Cut. Hello. Welcome to The

(02:09):
Deepest Cut. We have a new episode here with my
friend Greg LaFollette. So glad to have you here, Greg.
Normally I go right into like, here's who this person
is and and but I just feel like you wear
more hats. Actually, right now you're wearing a Kansas City
hat native to your home. But the metaphorical hats you
wear are actually many. And I wanted you because I

(02:32):
know there's like, there's not just your own songs. You
actually write songs in different lanes of your own self,
but then you're involved in songs in so many other
ways for so many others. Like, like just to distill
that down for people who are like, oh, I only
know him from one lane and not some others. Well, hello,
by the way.

S2 (02:49):
Hey, uh, good to see you. I mean, hear you, right? Yeah.
So I have worked in studio environments for going on
20 years. really close to 20 years, and worked on
hundreds of records in a lot of different capacities as
an intern, as an unpaid intern, as a paid intern, uh, engineering,

(03:11):
um production, as well as sort of, you know, uh,
performing on records and, and songwriting. And I've done touring
as a sideman. And I also work I currently work
part time at a church in Kansas City, Christ Church, Anglican,
part time there.

S1 (03:28):
What's your role there, by the way?

S2 (03:30):
I'm the musical worship leader, and a bishop told me
to say it that way. Musical worship leader. So yeah.
And also I was, uh, I took some classes and, uh,
became a spiritual director, um, a handful of years ago
as well. And so I try to as I'm getting older,
I try for my investments. I call them, like, stacked investments.

(03:52):
So if I'm producing a record, it would be great
if it served the church. Um, or if I'm, you know,
working with an artist. I don't think of it as
artist development as much as maybe spiritual director or, you know,
at least both both and kind of thing. And, and
think of it as discipleship or as, you know, companioning or,

(04:12):
you know, that sort of thing. And so, yeah, and
also this hat actually, this is a hat that my
best friend gave me seven years ago or something. And
it was in a really I was in a really
sad time, which we're going to get to real fast
here in a second. And it just came in the
mail and it's this kind of fancy. It's a Baldwin hat,

(04:32):
which is a Kansas City specific company. And it was just,
you know, it came with this note, this really, you know,
intentional note that said something like, you know, I feel
like you I feel like you feel like you're kind
of untethered or you're looking for a place to belong
or something like that, and just know that you will

(04:55):
always belong with me. And if you're feeling that way,
That way particularly put on this hat and remember it.
And so it's really gross. It's a gross like, you know,
it's a hat I would have gotten rid of. But um,
on certain days it feels like the right day to
wear it.

S1 (05:11):
I love that sentiment. I love that sentiment. Obviously, we
want to get into the song that you chose here
on The Deepest Cut. We interviewed songwriters about the song.
That's the most painful or difficult song to have written,
of course, like on public record that they want to discuss.
But before we do, like I just know for you,
there are different lanes in which you're even producing music

(05:32):
for like under your own name, right? There's even a
worship project for kids. There are, like you mentioned, a
church resources, for lack of a better word. Or maybe
that's the right word. Yeah. Can you just kind of
take us into. Yeah, even these are my lanes there.

S2 (05:47):
Yeah. I forgot about that hat. The one we're talking about. Uh, yeah.
So around 2017, I started I don't call it worship
music because, um, it's fine in a Christian context to
call it that. But on an airplane, when you sit
down next to a stranger and you say, like, I
make worship music, it doesn't mean anything to them, or
it means the wrong thing often. Or I make Christian music.

(06:09):
It's like, okay, but first let me apologize about Christian music.
And let me say, I get it that, you know, whatever.
But it's not that, you know, so I, I describe
the music I'm primarily making as an artist, as songs
for churches to use or songs for the church to use. Um,
and that is a lot clearer of an answer to

(06:30):
that kind of airplane new friend. And so, uh, yeah,
like I kind of have three different entities, both, you know,
as an artist. Greg LaFollette um, I'm kind of making
Congregational church resources as well as kind of personal devotion tools,
you know, which is a weird I know we're talking

(06:51):
about art, so I'm very aware of that. And then
I have a band with my wife, um, called West
Hype Manor, which is the name of the neighborhood we
live in, and we've released a few songs and releasing
more this year. And then I have a project called
Always and Everywhere, which is resources for kids. You know,
I mentioned I work at a church, and I realized

(07:14):
at some point, you know, a couple years ago that
like a third of our congregation are children, elementary school children.
You know, we have. And it was like we have
an amazing, you know, family life team, you know, but
if they were singing along to to videos and when I,
when I was in the room with them, it was like,

(07:35):
they are not enthused by this, you know? And it
really didn't take much for me to like I started
going in and singing with them personally, just like I
would do my, you know, opening set in the service
and then run over to the children's space and do
a song with them. And I was just so impressed
by them and encouraged, you know, even singing a song
like Come Thou Fount or something like that, I would

(07:57):
teach them that what thou means and maybe, you know,
hit Ebenezer real quick and like what we're talking about,
you know, and I'd leave melodious for them to, to
figure out, but, um, but yeah, man. Like they would
just they were just up for it and so enthusiastic
and it was really inspiring to me just to be
kind of in the room with them face to face,

(08:19):
connected in that way. And it really helped. I think
it really helps them. Um, and they deserve it. They're
a third of our congregation. They I want to pastor
them in that way. And so I recorded some songs that, um,
I believe in and that our, uh, clear. But but also,
I didn't want to like one of the downfalls of
children's music, which is not what we're talking about today,
but is that it oversimplifies and doesn't, doesn't dignify the kids.

(08:43):
And so I'm like a big Mister Rogers guy. And
so if you see me leading worship with kids, I'm
usually like on my back, you know, like a smashed
bug playing the guitar and, you know, whatever playing Simon
says worship basically with them and, and um, so getting like,
not only, like, condescending, you know, in, in a dictionary

(09:04):
term of it, like coming down to their level, but
also like realizing, man, these kids probably understand the Trinity
better than I do because of, like, all of the
stuff I'm. So I don't know, I'm so cynical. I'm
so biased by, you know, my upbringing, whatever. It's like,
you know, I'm not afraid to explain the mystery or

(09:25):
to not explain, but, uh, put forth the mystery of
the Trinity because it's like, use your imagination. It's probably
better than mine.

S1 (09:33):
Yeah.

S2 (09:33):
You guys got this figured out better than I do.
So those are the three kind of primary places. Um,
I'm also producing records often, um, for artists in that
same kind of world.

S1 (09:44):
I love that, by the way, as an aside, I
just want to applaud the holistic nature of like, you know,
you said, I'm the music. I'm the musical worship director here.
It feels like a lot of churches pay their staff
to get rid of the kids so that the adults
can do what they need to do kind of a thing.
And the fact that someone in your role is holistically thinking, well, hey,

(10:07):
if I'm musical worship director for this church and one
third of them are children, then we need to address
the children just as much as we do any other group.
That just feels very healthy and holistic to me, and
I think that's a plausible for what you're doing there.

S2 (10:20):
Amen, man.

S1 (10:21):
Um, obviously we want to talk about the song you chose.
Darkness is my closest friend. Where does that fit? I mean,
you just said these are kind of the lanes I
live in. Where does this fit in that? And then
I'd love to go into, you know, tell me about
the origins of the song.

S2 (10:37):
I so I think of the worship leader role not
as just like a song leader, but I think of
it as in a from a pastoral lens. And, uh,
and so I think of myself as a shepherd. And
so I'm trying to address things that I think need
to be addressed in, in sort of my circle. But

(10:58):
of course in often that translates to larger the larger
capital C church and that sort of thing. And I
think a song, a psalm like Psalm 88 is so
easy to appreciate from afar and be like, okay, yeah,
it's good that there's darkness in our spirituality or a
reference to the real realness of life, you know, um,

(11:24):
which of course includes death and darkness and sickness and
tragedy and, um, I'm not going to mention the beautiful
and counterbalancing things because those ones are the easy ones
to recognize, you know? So it's me kind of putting
forth this, um, this thing that can be easy to
move past quickly to kind of recognize and, but not

(11:47):
want to spend time with. And I get that like,
I'm not you know, there are times in life when
we're forced to spend time in those places. And I
don't think any of us, any of us would choose it.
You know, maybe some, but I would never choose it.
And so the lane is it's kind of a pastoral
lane where I'm like, I think I specifically and I

(12:10):
think we, my, my people and the church, um, could
stand to spend some time in this world. Now, the
idea of like, the importance of lament is decades. You know,
there's been a solid decade of people saying like, hey,
we got to do this. This is a part this
is a huge part of the Psalms and a huge

(12:31):
part of, uh, early spirituality and ways of relating to God.
And yeah, I guess I, I'm not claiming that it's
anything novel, you know, but I do think it's probably
something that we need to be reminded of pretty, um,
pretty consistently. Or it's easy to just kind of lose

(12:51):
track of it. And I think we need to do
that for ourselves, but also Because it keeps us soft.
It keeps us compassionate. It keeps us aware even when
we're not in that moment of tragedy. Um, someone else
is guaranteed. You know, and so it keeps our eyes
more open to see that. It gives us more grace

(13:12):
for people if they're rude to us. You know, um,
in the grocery line for no reason. It's like, well,
the actual reason is something brutal and horrible, you know?
So that's the reason. And then the origin of the song,
I mean, um, it just came out of a season where,
you know, I was kind of waking up and spending time, uh,

(13:34):
in the Psalms, you know, it's probably if I, you know,
confessional here. It's probably been quite a few years since
I've gotten outside of the Psalms in any meaningful way in,
in interacting with the Bible. Um, they're just like the
I just feel like I can relate to that part.
And some of the parts, of course, there's quotables in Peter,

(13:58):
you know, or, uh, you know, and I do. One
of my Lenten practices was reading a gospel account, uh,
which it's been it had been a while, and it's
been nice, but the, um, you know, like the rules
for life and the order of life, those things have
just felt, I don't know, more peripheral than how can

(14:22):
I be? How can I have a healthy relationship with
myself and with God? And the Psalms help me to
do that. Um, and so this is one that, of course,
you know, when the s hits the f, uh, when,
when trouble strikes, you know, uh, this is one that
that can accompany you there.

S1 (14:42):
Were you in such a season personally at the time,
or were you just reflecting on the Psalm?

S2 (14:47):
Yeah, yeah. So I was in a season, um, I,
there was an end to kind of a sudden end
to a long relationship that I had a lot of
hope in. And and so it was you know, it's
not once again, not anything novel or new or, um,
not anything that hasn't happened to zillion other people. But, uh,

(15:07):
it hit me hard and threw me, you know, and, um,
I had to, you know, I had to take, like,
anxiety medicine for the first time in my life. And
I had to, you know, uh, just 12 step programs and,
you know, support groups and, you know, stuff like that,
that that was kind of unprecedented for me a little bit.

(15:27):
And so, you know, I find, I think I found
solace in, in not being alone that like, bad stuff
happens to other people and tragic things happen to other people. And,
you know, that's like that's the secret of these kind
of intimate, vulnerable songs is that there is a a

(15:48):
companioning that happens with them, you know?

S1 (15:50):
Yeah. I think the resonance of the Psalms is in
that connective tissue that they form. It's in the it's
in the I'm in this to, you know, sort of
like whatever you can read into various psalms.

S2 (16:02):
Well and I think, I do think the, I think
Scripture is open to us for that, for us to
apply ourselves to it. And so, of course, you know,
this dude who wrote this Psalm, uh, I saw recently,
it's spelled h e m a n, which is probably
like a I don't know how to pronounce it, but

(16:23):
I've been saying He-Man over and over again. You know,
I can't I don't know what he was going through,
but I know it was brutal, you know? And I think, like,
as I was feeling despairing or hopeless or helpless, you know,
him sharing his experience really helped. So I think, like,

(16:43):
I think most of the songs you've probably dealt with
these hardest songs for artists to write, they're probably I
think a lot of them have very personal details. They're
written in their words, their account, their hometown, their ex-lover's name,
you know, whatever. And songs like, um, Brick by Ben
Folds or Fire and Rain, James Taylor, or like even Graceland, surprisingly,

(17:09):
by Paul Simon. You know, it has that, uh, she
comes back to tell me she's gone. As if I
didn't notice, as if I didn't know my own bed.
As if I'd never noticed the way she brushed her
hair from her forehead. And then this, like, striking, clearest communication.
And she said, losing love is like a window in
your heart. Everybody sees you're blown apart. Everybody sees the

(17:31):
wind blow. You know, there's I think often when we
think of vulnerability, we're not thinking of someone setting someone
else's words. And I think that's maybe one of the
most interesting things about this song is it was me
kind of applying my situation, but also using this other
person's words. I think I do it for a couple
of reasons. One, it protects me a little bit. It

(17:54):
makes me not say things that maybe I would regret later.
You know. So, yeah, just to be, like, totally honest,
it's it is a little less vulnerable for me to not,
you know, divulge details or to, you know, um, but
it also, I feel like just kind of keeps me
between the ditches in my relationship with God. Um, that

(18:17):
being said, I often wonder if the Psalmists were being
sarcastic or regretted things they said. In these moments. I
know that as I have prayed to God, um, as
I did pray to God in that season, I say,
I mean, I said some stuff that was was not okay,
you know, like, yeah. So I'm not saying that that

(18:38):
there is like a censoring that's happening, but I do
I do find comfort in kind of trying to live
through these established, um, means, does that make sense?

S1 (18:51):
Yeah, I get it that there are guardrails in place
for this kind of thing. I will say this though
to me, the Psalms, like you just said, I've said
some things that weren't okay. And yet when I read
the Psalms, largely what I walk away with is everything's okay. Yeah. That,
that in my ability to communicate with something bigger than me,
to have this relationship, you know, like I'm, I'm allowed

(19:17):
to be fully myself and to bring all of that
to bear in it. And the Psalms are kind of
this account of that, right?

S2 (19:25):
I mean, of course. Yeah. And when I say not okay,
I mean, not suitable for public consumption.

S1 (19:31):
Sure. Sure. Of course.

S2 (19:33):
I asked you before the podcast, can I, can I curse? And, uh,
and God has answered that question, and he's okay with
with cursing, it turns out.

S1 (19:42):
Sure.

S2 (19:43):
But, yeah, I think, uh, I think you're exactly right. Yeah. No,
no holds barred, really. You know, and this is maybe
the best example of that in the whole Bible, where
I feel like he's assigning blame. He's saying, like, God,
you did this. You put me into a pit. Not
I find myself in this random evil has happened to me.
It's like, no, no, no, you did this. You could

(20:05):
have not done it and you did it. What's up
with that? I'm not okay with that. That makes me
really mad. And and I once again, it's like when
we apply our situations to this. When I applied my
situation to this, it's like. That's how I felt, man.
I felt bitter and I felt mad. I felt like wronged, um,

(20:26):
beside feeling disappointed and disillusioned and those things, I felt like, um,
injustice and active emotions. Not only grief or loss.

S1 (20:37):
Yeah. And yet those things are sacred spaces, too, right?
They're canonized. They're they're memorized. They're celebrated and intended to
be lived into as well. Like any other psalm.

S2 (20:49):
Yep.

S1 (20:50):
Um, Greg, I this feels like the appropriate. I mean,
I'd love to let people actually hear what we've been
talking about. I'd love to have you take us into
your song.

S2 (20:59):
Let me say one last thing. I think the I
can remember when I wrote this song thinking a lot
of artists write laments or grief from the other side
of it, or at least they deliver it from the
other side of it. And so I remember feeling like
if I was in a valley, there's a lot of

(21:20):
resources and a lot of, um, yeah, a lot of
resources and a lot of art that's on the other
side of the valley and back up on the other
mountaintop and saying, yeah, I suffered back then, but look
at me now. I made it through, which is giving hope.
I'm not. There's nothing wrong with it. I remember feeling
like I want to share this in all of its

(21:40):
sloppiness and all of its complexity, um, in its sort
of just be raw, you know, and I there are
mostly there are just a lot of practical things like
it's hard to promote a record when it's hard to
get out of bed, you know? Or you know, it
turns out you don't want to go and be in
front of a hundred people, um, when you, you know,

(22:02):
haven't showered in a couple days or whatever. So I
get that. But I also do I do want to,
I don't know, I want to I find myself in
the same place as everyone else, like I'm past it
in whatever ways I'm past it. I'm definitely not past
it in some ways. But yeah, I don't know. I
guess I just want to say to the people who
are in the Valley, because I can't, I'm with you.

(22:23):
I want to say I'm with you as much as
I can be, and I do know how it felt,
and I maybe don't know how it feels right now
to you. But I do know how it felt for me.
And I know how it feels sometimes for me right now.
And you're not alone. And I'm saying this to you.
I'm not going to try to be overly simplistic and
give you any sort of easy answer. I'm just saying

(22:46):
that you're not the only one. So I'm Greg LaFollette.
This is, uh, Psalm 88. Darkness is my closest friend.

S3 (22:58):
My father. I am all alone. I cannot find a friend.
This sorrow has become my home. My tired eyes are dim.

(23:30):
In grief. Lord, I'm calling out to you. I'm reaching
for your hand. But darkness is my closest friend. Darkness. Darkness.

(24:08):
Darkness is my closest friend. Darkness is. Darkness is. Your

(24:42):
wrath is sweeping over me. Your terrors are too All
day long I watch them cry. Around me like a flood.

(25:12):
They have completely. Come over me. They have completely. Cut me.

(25:35):
Darkness is my closest friend. Darkness is the darkness is.
Darkness This is my closest friend. Darkness is darkness. You

(27:11):
have completely. Caught me. You have completely. Caught. Me.

S1 (27:31):
You've been listening to the deepest cut part of the
Rabbit Room podcast network audio production and theme music by
Isaac Vining. Logo and identity work by Meg Cook. The
Deepest Cut was created and hosted by me, Matt Conner.
Thank you so much for listening.
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