Welcome to the Deep Dive. So if you're looking
for a complete, coherent, easily marketable brand
identity. Yeah. Well, you've definitely come
to the wrong place today. That's putting it mildly.
We're basically trying to shortcut your understanding
of Joseph Will Oldham. He's an American singer
-songwriter and actor too. And what really defines
him is how he... intentionally uses confusion,
almost strategically, you know? Yeah, that's
a perfect way to frame it. We are diving deep
into the career of someone who's incredibly prolific,
been active since 93 right up to now, but also
like deliberately elusive. Right. Our mission
really is to unpack what we're calling the pseudonym
paradox. It's this idea that for him, maybe stability
and connection actually come through. Constant
instability in disguise. Strange, right? It really
is. So born Joseph Will Oldham, January 15, 1970,
Louisville, Kentucky. His musical identity is
built on these, well, shifting sands. Before
we even get to the music itself, just look at
the names he used early on. Especially in those
foundational years like 93 to 97. We've got Palace,
Palace Brothers, Palace Songs, Palace Music.
And that was just the beginning. Just scratching
the surface. And all of that confusion eventually
led to the name that's stuck. The one that feels
almost mythic now, Bonnie Prince Billy, which
he adopted in 98. OK. But to really get why he
needed all these masks, these different names,
kind of have to look at his background. It's
maybe not what you'd expect. It's not the typical
rock star origin story. Not at all. This wasn't
someone who dropped out to go on tour. He came
from a really thoughtful pre -academic. Background.
He graduated from J. Graham Brown School back
in 88. And while he was, you know, trying out
acting roles in places like Brooklyn, L .A.,
Bloomington, he was also attending Brown University.
Sporadically, it sounds like, but still. Right.
Dipping in and out. And his family environment,
that was pretty intellectual, too. His mom was
a teacher, an artist, his dad, an attorney and
photographer. So the artistic roots are definitely
there, but maybe with a more academic approach.
Which leads perfectly into this key little detail,
something that really sets the tone for his whole
career, I think. The origin of the music itself.
Exactly. His first real move into making music
wasn't like starting a garage band. It actually
began as a project, an academic project for his
ethnomusicology professor at Brown, Jeff Todd
Titan. Which is fascinating, isn't it? It suggests
right from the start, he saw making a song or
an album or even an artistic identity as maybe
as much about intellectual structure, a kind
of study and performance and folk tradition as
it was about just raw personal expression. Yeah,
it feels much more considered than just, oh,
we got a new drummer, let's change the name.
This feels like a deliberate strategy, almost
like controlling the narrative from the start.
So for you, the listener, getting the why behind
all these disguises, that's really the key. to
unlocking his entire body of work. Absolutely.
That intentional rationale, that's the philosophical
core we really need to dig into first. If you
look at that initial period, the palace era,
93 to 97, it was just chaotic. Gizzying, yeah.
Palace, palace brothers, palace songs, palace
music. If you were trying to follow him back
then as a fan, you'd just feel completely lost,
I imagine. And he knew that. It wasn't an accident.
He was consciously trying to signal that things
weren't continuous. Precisely. His fundamental
belief was that different records, records with
different themes, different sounds, and maybe
most importantly, different collaborators, they
just shouldn't be seen as coming from the same
band, the same unit. That's such a direct challenge
to how the music industry usually works, isn't
it? Totally. Most bands, they find a name, they
stick with it, and that name becomes a brand
that promises something consistent. Oldham just
threw that whole idea out. He basically said,
look, if I put out a record under one name, you're
going to expect the same people, the same kind
of sound next time. Right. But he wasn't doing
that. He was constantly cycling through musicians,
dozens of them. One year it might be super lo
-fi acoustic stuff. The next it's louder, full
band rock. So the name change was almost like
a warning label. Exactly. He felt he had to change
the name so the audience would know right away,
OK, this is a fresh project. It might be his
writing, but maybe not much else is the same.
It's almost anti -commercial, really. Designed
purely for artistic freedom. Absolutely. If you
bought There Is No One, What Will Take Care of
You by the Palace Brothers in 93, you shouldn't
be shocked when Viva Last Blues by Palace Music
comes out in 95 and sounds completely different.
The name change itself was the heads up, like
caveat emptor, or maybe caveat expectator. Let
the listener beware of their own expectations.
Ah, yeah. It gave him total permission to just
reinvent his recording style, the instruments.
Everything with each release. Total freedom.
That intellectual side shows up even in the choice
of the word palace, doesn't it? It sounds so
grand, but the music often feels quite grounded
or even raw. Well, there's a great little anecdote
about that. He mentioned, I think it was in a
95 KCRW interview, that one of the early names
he used, Palace Flophouse. Okay. That was directly
inspired by reading John Steinbeck's Cannery
Row. Ah, okay. Makes sense. Yeah, that book,
you know, it's all about these societal outcasts,
drifters squatting in this rundown old building.
It's kind of a perfect metaphor, isn't it? The
structure that maybe used to be grand, but now
it's crumbling and it's housing the shifting
group of artistic transients. That fits perfectly.
So, okay, after years of this deliberate chaos,
this flux, why did he land on Bonnie Prince Billy
in 1998? Why did that one stick? Why trade the
constant change for something that felt... Well,
more permanent. Well, I think the permanence
is maybe part of the construction itself. It's
like he was building something designed for mythic
endurance this time. And the name itself, it
seems like he pulled it together from three pretty
distinct inspirations. Like he was searching
for something with deep roots in history and
folklore. Okay, what are the layers? So the first
layer, he said, is historical. He liked the mellifluous
sound of Bonnie Prince Charlie. The Scottish
claimant to the throne. That's the one. The romantic
figure. The failed rebellion. brings this sense
of like royalty but also tragedy yeah a sound
that's elegant but also kind of sad which definitely
fits a lot of his music exactly Then the second
layer, it's a nod to music history, specifically
American performers. He mentioned thinking about
the structure of names like Nat King Cole. Oh,
interesting. Like the rhythm and weight of the
name itself. Yeah, that careful, balanced cadence.
It shows an appreciation for how performance
names can sound inherently American, almost build
on rhythm. Okay, so royalty, musical structure.
What's the third? The third one connects it firmly
to American outlaw mythology. He often suggested
this might have been more subconscious, but it
links to William Bonney. Billy the Kid. Billy
the Kid. So in one name, Monty Prince, Billy,
you've got Scottish royalty, classic American
performance structure and a legendary American
outlaw. Wow. So the name itself suggests someone
who's both like elevated, but also a rebel. A
romantic figure outside the usual rule. Precisely.
Outside the law, whether that's society's law
or music's law. But the really crucial part here,
the so what. for you listening, is why go to
all this trouble? He actually gave a pretty clear
reason for the pseudonym's main purpose, didn't
he? He did, and this is really the core artistic
commitment, I think. He explained that the name
allows both the audience and the performer to
have a relationship with the performer that is
valid and unbreakable. Okay, valid and unbreakable.
What does that actually mean in practice? What
kind of relationship is that? It's basically
a protection mechanism. Think about it. If he
releases incredibly personal, vulnerable songs
under his real name, Will Oldham, then maybe
any personal stuff that happens to Will Oldham
in his life, failures, changes, just growing
up, could potentially mess with how the audience
hears the art. Right, the music gets tangled
up with the biography. Exactly. The music becomes
burdened by the man. So the pseudonym, Bonnie
Prince Billy, acts like a shield. It protects
the pure artistic project from the everyday realities
of his private life. So Bonnie Prince Billy is
like this mythic character. Sort of an avatar,
yeah. A consistent artistic lens. The audience
isn't really asked to relate to Joseph Will Oldham,
the guy who pays taxes or gets married. They're
asked to relate to this persona who deals in
these haunted melodies and big existential questions.
It creates a space where the emotional truth
of the song can exist on its own, untainted by
the singer's personal life, making that relationship,
as he says, unbreakable. That's the idea. It
keeps the focus on the art. That distinction
focusing on the project over the person that
seems to run through everything he does. So now
we kind of get the shifting identities. Let's
talk about the music itself, the actual sound,
which seems just as contradictory as the name
sometimes. Yeah, the sound is definitely defined
by its rawness, its refusal to just settle into
one thing. Critics often point to this foundation
in like a do -it -yourself punk aesthetic and
blunt honesty. Even when it's acoustic folk music.
especially then sometimes there's often this
lo -fi immediacy to the recordings it feels intentionally
stripped down you know like they're deliberately
avoiding polish to focus purely on the emotion
and the lyric and the melody it connects directly
back to that self -reliant vibe of 80s punk i
think and the result is this huge mix of genres
that people try to pin on him it tells you right
there he resists easy labels we see things like
country rock freak folk Gothic country. Lo -fi
indie folk, alternative country. Yeah, the list
is long. It's a sprawling catalog of influences.
It really points to a deep knowledge and appreciation
for the whole history of American roots music.
But it's always delivered with this kind of modern,
often unsettling edge. If you listen closely,
the themes keep coming back. mortality, moral
ambiguity, these stark rural landscapes. Which
explains that very specific description you sometimes
see. Appalachian post -punk solipsist. Right.
It sounds like a mouthful, doesn't it? It really
does. Can we break that down? What does Appalachian
post -punk solipsist actually capture when you
put it all together? Okay, yeah. It actually
synthesizes it really well. The Appalachian part,
that's pretty straightforward. It points to his
Kentucky roots, his use of folk and country structures,
you know, the haunted sounding melodies, traditional
instruments sometimes, the storytelling style
common in Southern music. Got it. And post -punk.
That captures the recording style, the raw, maybe
anti -establishment feel. It's that lo -fi aesthetic
we mentioned, the emotional immediacy resisting
that slick commercial production sound. Okay.
Appalachian post -punk and solipsist. Yeah. That
feels like the most abstract part. That ties
right back to the pseudonym, actually. Solipsism,
philosophically, is the idea that only one's
own mind is sure to exist. In his songwriting,
it kind of translates to this. intensely personal
almost sealed off focus the lyrics are often
deeply introspective dealing with these internal
psychological worlds relationships defined purely
by the individual's viewpoint a lot of existential
dread the pseudonym the prince acts as the barrier
that allows this intensely personal solipsistic
stuff to come out without maybe implicating the
man will oldham in that extreme vulnerability
the character speaks the difficult truths That
intensity is definitely amplified by his voice.
It's instantly recognizable, but it's not technically
powerful, is it? It's actually quite fragile.
Yeah, fragile is a good word. It often gets described
as like a fragile sort of warble frittering around
haunted melodies. It's incredibly expressive
because it's vulnerable. It doesn't sound like
a voice that should be tackling these huge themes,
but it does with this unnerving conviction. It
makes you lean in, you know, to catch the lyrics,
which are often really complex and literary.
His discography is just huge. But if someone
wants the essential starting points, the albums
that critics consistently rate highly, where
should they look? OK, yeah, the roadmap. You
absolutely have to start in the palace era. There
is no one what will take care of you from 93
under the palace brother's name. That's foundational.
Right. Then you see the evolution with Viva Las
Blues in 95, credited to palace music. That shows
his first big shift towards fuller arrangements.
OK. And then the essential Bonnie Prince Billy
album, the one often called his masterpiece,
is I See a Darkness from 1999. Right. The title
track, everyone. knows exactly those three albums
together give you a pretty concise history of
how his sound developed right through the 90s
another defining thing about his output is how
much he collaborates which again seemed to reinforce
that idea that the project is bigger than just
him he doesn't only make solo records no his
collaborative albums are crucial like his partnership
with the guitarist matt sweeney they did super
wolf together back in 2005 which was amazing
So good. And that partnership was so strong,
they actually came back and did a sequel, Superwolf
again, 16 years later in 2021. Those records
really show a darker, more electric side of his
writing. Sweeney's guitar work, it's so precise,
a little eerie sometimes. It's the perfect counterpoint
to Oldham's voice. And he takes those collaborations
into really different territory too, doesn't
he? bringing his folk thing into unexpected genres.
Yeah, the Tortoise collaboration is a great example.
In 2006, he teamed up with Tortoise, the legendary
experimental post -rock band from Chicago, for
an album called The Brave and the Bold. What
was that one like? What's fascinating is it was
entirely a covers album. It was a chance for
him to reinterpret songs by artists ranging from
Richard Young's to, believe it or not, Devo.
Devo, wow. Yeah. It's a perfect example of letting
the collaborators dictate the context and the
sound, even if it pushes him way outside of traditional
folk. It's about the project. And more recently,
he joined forces with another songwriter known
for kind of poetic, mysterious work. Right. The
2021 album with Bill Callahan, Blind Date Party,
that's another highlight. They both have that
really literate, philosophical style. And seeing
them work together, often covering other artists'
songs again, it just underlines his focus on
conversation and synthesis, not just his own
brand. So he collaborates outwardly. But he also
seems to collaborate with himself, turning his
own back catalog into new material. This is where
the name thing gets even more complicated. Those
reworking albums are really interesting, almost
like philosophical exercises. In 2004, he released
Sing's Greatest Palace Music. He took those early,
really raw lo -fi palace songs and re -recorded
them, but this time with a more polished, considered
approach, and importantly, under the established
Bonnie Prince Billy name. So the name dictated
the style of the reworking. Seems like it. And
then he did something similar again, but switching
the name yet again. Using his birth name this
time. Exactly. For the 2018 album Songs of Love
and Horror, he revisited material again, but
released it explicitly as Will Oldham. That feels
really significant, given everything we've said
about the pseudonym being the unbreakable performer
contract. It is hugely significant. Releasing
some of his most intimate material under his
given name suggests that maybe, sometimes, the
mask does come off. Maybe the relationship he
wants with that material or at that moment is
different, perhaps more vulnerable, more direct,
less wrapped in myth. Like, the man is finally
ready to own the songs that the prince first
sang. When an artist operates so far outside
the mainstream, like he'd does, often the real
measure of their impact is how they influence
other artists, right? And Oldham's reach seems
massive. It crosses genres, generations. It really
does. And the biggest moment, the one that undeniably
brought his work to a much wider audience, was
the Johnny Cash cover. I see a darkness. Yep.
Cash recorded that Bonnie Prince Billy song for
his third American album, Solitary Man, back
in 2000. For an artist known for being such an
outsider, having a giant like Johnny Cash cover
that specific song. It really cemented Oldham's
place in that lineage of great, dark American
songwriters. And it wasn't just a cover. The
connection was more direct than that. That's
right. The mutual respect was clear. Oldham didn't
just get covered. He actually provided backing
vocals on Cash's recording. Wow. Can you picture
that? The sort of outlaw prince of modern folk
standing there with the man in black, adding
his fragile voice to his own song as Cash transforms
it. It feels like a real torch passing moment.
And that influence just spread out from there,
didn't it? Globally across all sorts of music.
It really speaks to how strong his songwriting
is structurally, that it works in so many different
styles. Take Rosalia, the Spanish singer who
mixes flamenco and experimental pop. Yeah. She
covered I See a Darkness, that song about deep
existential crisis on her very first album, Los
Angeles, going from Kentucky folk introspection
to Spanish avant -garde pop. That's incredible
range. And rock legends. covered him too. Absolutely.
Marianne Faithfull started including his song
A King at Night in her live shows around 2003.
And then you have people like Steve Aidy, Mark
Kozilek, highly respected songwriters themselves
covering his work. It confirms his status as
a real songwriter's songwriter. But maybe the
most surprising covers come from completely different
ends of the musical spectrum. You mean like Catatonia?
Exactly. A Swedish heavy metal band. Yeah, Catatonia,
known for their atmospheric, melancholic metal.
They covered Oh How I Enjoy the Light and they
even wove parts of the Palace Brothers song You
Will Miss Me When I Burn into one of their own
tracks. It shows that his themes, darkness, mortality,
they resonate even in the metal scene. And his
work pops up in TV shows too. Right, like Deer
Tick's cover of Death to Everyone was used really
effectively in the Western series Hell on Wheels.
The list keeps growing. Cadaver's condition covered
black. Influence is broad. This feels like a
good point to circle back to that do -it -yourself
punk aesthetic. In today's world, that ethos
gets tested by how music is distributed right.
His stance on streaming services seems like a
very practical application of his whole philosophy.
It's a huge statement, really, a statement of
integrity. He's made a conscious choice to keep
many of his solo albums off Spotify, the biggest
platform out there. That must cost him in terms
of reach and income. Massively. But he sees it
as necessary. And his reason goes right to the
core of it. He basically says he disagrees with
how they treat musicians. Simple as that. He
feels the payment model, the way music is kind
of devalued, is fundamentally exploitative. So
by withholding his work. He's reinforcing that
anti -commercial, anti -establishment stance
that he started with way back in the palace days.
It's saying, look. I value the integrity of this
project and the ability for artists to make a
living more than I value mass access on these
terms. It forces you, the listener, to engage
with the music differently, maybe more intentionally.
It reinforces that unbreakable relationship idea,
even if it's less convenient for the consumer.
OK, let's completely switch gears now, because
for people who only know the music, maybe the
biggest surprise is that Will Oldham has had
this whole other career, a really robust and
continuous one as an actor, often under his own
name. Right. It's not just a side hobby. It's
a parallel path that actually started before
his music career really took off. Acting was
his first ambition. Seems like it. He moved to
Hollywood specifically to act after he landed
his very first film role. And it was a pretty
significant part, too. And in a serious, acclaimed
film. from the start. Yeah, his first role was
playing the teen preacher Danny Radner in John
Sayles' fantastic 1987 drama, Mate One. Which
is about the coal miners' strike, the Battle
of Mate One. Exactly. A powerful historical film
about Appalachian labor disputes. Playing a teen
preacher right off the bat placed him in this
role, demanding deep moral conviction, intensity.
Themes you can definitely hear echoing in his
music later on. But he also had a brush with
something much more mainstream early on, before
he really committed to the indie world. Yeah,
that range is part of his unique path. After
Matewan, he ended up playing Chip McClure, the
father of baby Jessica, remember her? The baby
rescued from the well. Oh, wow. Yeah, in the
1989 TV movie Everybody's Baby, the rescue of
Jessica McClure. So a brief detour into mainstream
sensational drama, totally different from the
artistic isolation of his music. He was also
in a film called Thousand Pieces of Gold around
1990. But like his music, it seems his most lasting
connections in acting came from the independent
film world, especially with director Kelly Reichert.
Absolutely. That partnership really marked his
return to acting in the mid -2000s. He starred
as Kurt in her 2006 film Old Joy. Which is a
beautiful, quiet film. It really is. Just about
these two estranged friends on a camping trip.
And Kurt, his character, is defined by introspection,
a feeling of displacement, a quiet searching.
It feels like a perfect mirror to the Bonnie
Prince -Billy persona in many ways. And he worked
with her again after that. Yeah, he had a smaller
role. as the character Icky in her next film,
Wendy and Lucy, in 2008. He also found another
key collaborator and director, David Lowery,
right? Showcasing more of that philosophical
side on screen. Yes. Lowery cast him first in
a short film called Pioneer in 2011, and then...
Maybe most memorably, as the character called
the Prognosticator in the 2017 film A Ghost Story.
Right, where he delivers that incredibly long
monologue. That amazing monologue, all about
legacy, time, questioning the whole point of
existence. It feels like something Bonnie Prince
Billy could have written himself. But just when
you think you've got him pegged as this super
serious, somber indie guy, he completely throws
you a curveball by embracing total absurdity
and lowbrow comedy. That DIY punk thing again,
maybe? embracing stuff that just punctures any
sense of high seriousness. His appearance in
Jackass 3V. In 2010, yeah. It's just brilliant
comedic contrast to his artistic reputation.
He shows up as himself playing a gorilla trainer,
but the story behind the cameo is almost better.
Okay, tell us the negotiation story. So he agreed
to do this absurd physical comedy bit. Right.
But apparently, as part of the deal, he wrote
a theme song for one of the filmmakers, Lance
Bangs. But not just any theme song. Yeah. He
wrote it in the style of a Saturday morning cartoon
show theme. Get out. The guy known for Gothic
Country wrote a cartoon theme for Jackass. Exactly.
The sheer contrast is just... peak Oldham. It
shows how comfortable he is with paradox, with
performance art. It suggests that maybe all creative
output, whether it's a haunting ballad or a silly
cartoon tune, is just another valid project for
him. That dry, surreal humor pops up in some
niche TV stuff too. Yeah, he played Pastor Pigmeat
in an episode of that infamous MTV charity show
Wondershowsen. Oh, Wondershowsen, right. And
he voiced a reverend character in the animated
series Xavier, Renegade Angel. He clearly enjoys
using that distinctive voice for weird comedic
effect sometimes. But maybe the most out there
project mentioned in the source material was
that documentary that was supposed to be a reality
TV pilot. Oh, Tripping with Keva. Yeah, from
2004. What was the deal with that? The filmmaker,
Kaviza Hedy. had this wild idea for a reality
series where he'd take psychedelic drugs, specifically
psilocybin mushrooms, with a different celebrity
guest each episode. Seriously? A reality show
pilot about celebrity mushroom trips in 2004?
Yep. The short film showing him and Oldham taking
the mushrooms was shot as the pilot? Obviously,
it never got picked up by a network. I can imagine.
Why not? Right. But the film itself did eventually
get an official release years later in a box
set of Zahedi's work. It's just another example,
isn't it, of Oldham's willingness to jump into
projects that just completely blur the lines
between documentary performance art and maybe
controlled chaos, kind of like the structured
chaos of his musical identity. OK, let's round
out the career part with his voice work, which
often seems to bring things back to his roots,
back to Kentucky. Yeah, his narration work is
really well regarded. He lent that unique voice
to some important documentaries like Madam and
Little Boy in 2009, which is about atomic weapons.
And also the 2010 film Music Makes a City, all
about the history of the Louisville Orchestra.
So he's using his voice to tell these bigger
stories, but also regional ones. And he's even
made his mark in modern video games for people
into interactive narratives. He has. He did voice
work for the 2013 game. Kentucky Route Zero.
But more than that, he apparently served as inspiration
for the character actually named Will in the
game. Oh, cool. Yeah, and that game is known
for its really surreal storytelling, exploring
American mythologies, especially regional ones.
So having him involved lends this authentic,
grounded, but also slightly haunted quality to
its version of Kentucky. So before we try to
wrap all this complexity up, we should probably
mention that this man of a thousand public faces
does have a steady private anchor. Right. He
married the textile artist Elsa Hansen back in
2016, and they had a child together in 2018.
So there's this grounded personal life happening
alongside the constantly shifting, performing
artistic identity. Even the ultimate shapeshifter
has a private reality away from the prince or
the prognosticator. Okay. So after this whole
deep dive, how do we synthesize this? What's
the main takeaway for you, the listener, from
this whole pseudonym paradox of Joseph Will Oldham?
I think the core idea, the thing that should
really stick is that the only real consistency
in his entire career is his embrace of intentional
inconsistency. It's like he operates under this
unified theory of creative work, meaning whether
he's burning through five band names in five
years or starring quietly in an indie film like
Old Joy or, you know, writing a theme song for
Jackass. It's all unified by this deep, almost
academic commitment to the artistic project itself.
Right. He forces the audience to focus on the
thing being made. the album, the film, the song,
the collaboration, rather than getting comfortable
with a single predictable personal brand. Exactly.
It's a career built on deliberately managing
identity in order to maximize artistic freedom.
Which leads us perfectly into our final thought
for you to chew on after this is over. Okay.
So we established early on that the stated main
reason for the Bonnie Prince Billy pseudonym
was to create this unbreakable relationship between
the audience and the performer right to protect
the art from the man right but We also know he
works continuously under his birth name, Will
Oldham, for all his acting, his narration work,
and even for specific albums like Joya or that
really significant rework album, Songs of Love
and Horror. So that raises a really interesting
question about what that artistic contract actually
is. If the prince is the dedicated mythic performer
of the songs, what does the simultaneous work
as Will Oldham tell us about the relationship
he wants with that material? yeah does the name
will oldham serve a totally different audience
maybe one for his film work or narration or do
the two names will oldham and bonnie prince billy
just represent two different but equally serious
sides of the same huge artistic project one being
the sort of mythic public performance the other
may be more direct unmediated communication It's
a really fascinating way to think about how identity
gets managed in the creative world today, where
that line between the artist and the art is always
getting blurred. Definitely something to think
about as you explore his incredibly complex but
always captivating body of work. Absolutely.
Thank you for diving deep with us today.