Welcome back to the Deep Dive. Today, we're tackling
an artist whose career is, well, anything but
straightforward. We're diving into Rikki Lee
Jones. Yeah, Rikki Lee Jones, born back in 54,
Chicago, and her career. It's now hitting five
decades, 15 studio albums. 15. And the thing
is, you can't just draw a straight line through
them, can you? Not at all. It's zigzags, loops,
sharp turns. Our mission today really is to unpack
that, to figure out why she's seen as just so
individual, so eclectic among singer -songwriters.
Okay, so let's start there. Eclectic. It's almost
an understatement. The minute you start listening,
you realize trying to pin down a genre is...
Kind of pointless. Completely. She pulls from
rock, R &B, pop, soul, definitely jazz. But it's
not like she just dabbles. She, like, embodies
these things then moves on. Right. And the critics
picked up on this early. All music, I think,
really nailed it. They called her, hang on, yeah,
an expressive and smoky instrument and a composer
who can weave jazz, folk, and R &B into songs
with a distinct pop sensibility. That word weave
is key, isn't it? It's not just throwing styles
together. Exactly. It's integration. She makes
something new out of those threads. And the industry
kept noticing, even when she wasn't exactly chasing
hits. Two Grammys, eight nominations total. And,
you know, for context, VH1 ranked her number
30 on their 100 Greatest Women in Rock and Roll
list. That was back in 99. So she's got that
historical cred, but she's not just a legacy
act. Not even close. Her latest album, Pieces
of Treasure, from just last year, 2023. Right.
The one focusing on the Great American Songbook.
Yeah. And it got her another Grammy nomination,
her eighth, for Best Traditional Pop Vocal Album.
That really says it all, doesn't it? Nearly 50
years in, still getting nominated, and in a category
like traditional pop, after starting out with
this unique kind of beatnik rock jazz thing.
That versatility is just, wow, it's incredibly
rare. So if her music is this complex blend,
where does that DNA come from? We need to go
back. Right. To her roots. Absolutely. You have
to look at her family. She was the third of four
kids born to Richard and Betty Jones. And named
after her father, Richard. Yes. And Richard Jones
wasn't, you know, an accountant. He was a singer,
a songwriter, a painter, a trumpet player, a
creative soul. You can see the line right there.
Instantly. The multi -talented, maybe slightly
restless artist thing, it's inherited. And then
there's the contrast with her mother, Betty,
raised in orphanages in Ohio. Yeah, quite a different
background. So you have this childhood environment,
probably full of artistic expression from her
dad, but maybe also this undercurrent of searching,
instability, reflecting her mom's upbringing.
They lived in Phoenix mostly during her formative
years, ages 4 to 14. Right, but moved around
a bit even then. That troubadour thing, that
sense of being on the move, it probably started
really early. But the performance style, the
theatricality, the way she tells stories and
songs. That goes back even further, doesn't it?
Oh, yeah. Straight back to vaudeville. Her paternal
grandfather, Frank Pegleg Jones. Pegleg Jones.
What a name. Isn't it great? He and her grandmother,
Myrtle Lee, were Chicago -based vaudevillians.
And his act explains so much about Ricky Lee's
presentation later on. Totally. He was a singer,
dancer, comedian, played the ukulele, did soft
shoe, acrobatics, comedy routines, a real all
around entertainer. So when you hear those early
tracks like Coolsville or even the conversational
bits in Chucky's In Love. It clicks. Right. It's
not just folk storytelling. It's got that stagecraft,
that character work, that almost musical theater
feel. That's Peg Leg's legacy in her work. And
she really dives into all this in her memoir
from 2021 Last Chance Texaco. Chronicles of an
American Troubadour. Essential reading, absolutely.
And that title. From the song. Yeah, The Last
Chat's Texaco, which itself got a Grammy nomination
way back in 1980. The memoir connects the dots,
you know. The transient, artistic, sometimes
difficult childhood, and the very specific, stylized
art she created. You see how the life shaped
the music. Okay, let's shift gears. Fast forward
to the mid -70s. California. Coffee houses. And
then... boom stardom right so 1975 she's 21 living
in venice california singing in bars coffee houses
doing jazz standards remember the vaudeville
roots but also her own stuff and this is where
she starts collaborating yeah she meets alfred
johnson they co -write some key tracks for her
debut like weasel and the white boys cool and
company and then comes the meeting that became
legendary the troubadour 1977 elf Tom Waits.
Ah, yes. Tom Waits. A whole chapter of rock mythology
right there. Two incredibly unique artists. They
dated for about two years, split up in late 79.
And that relationship, or at least that circle
of friends, led directly to her breakthrough
hit. It did. Chucky's in love. Story's great.
Their friend Chucky Wise calls them up one day
in 77, totally out of the blue, just to say he's
fallen in love. And she turns that phone call
into that song. Yeah, captures that moment, that
cool conversational vibe perfectly. It is the
announcement. Which leads to the debut album,
Ricky Lee Jones, March 1979. And it wasn't just
a hit. It was a moment. A phenomenon. Number
three on the Billboard 200, platinum. And Chucky's
In Love goes all the way to number four on the
Hot 100. Just huge. And look who's playing on
it. Dr. John, Randy Newman, Michael McDonald.
Right, that tells you something. She wasn't seen
as some small indie artist. She arrived commanding
respect, operating at the sophisticated intersection
of jazz, rock, pop. And Youngblood was another
hit too, right? Top 40. Yep, hit number 40 later
in 79, so multiple successes right out of the
gate. Then the Grammys in 1980. Four nominations.
Four. Song of the Year, Best Pop Vocal Female,
Best Rock Vocal Female for Last Chance Texaco.
And the big one, Best New Artist, which she won.
Exactly. That cemented the critical acclaim.
But the real explosion into public consciousness
happened even earlier. The serenade live appearance,
April 79. That was it. She performs Chucky's
in Love and Coolsville. Nobody really knew who
she was on that massive scale. And then suddenly
everyone did. Overnight sensation, truly. And
the press just ran with it. Time magazine calls
her the Duchess of Coolsville after her first
pro show in Boston. The perfect nickname. It
captured everything. The voice, the style, the
attitude. And that image gets locked in with
the Rolling Stone cover. August. August 79. Annie
Leibovitz photo. The iconic one. Crouched down,
black bra, white beret. It just screamed unique,
authentic, beatnik, cool. It's interesting, too,
that story about Francis Ford Coppola wanting
her and waits for the One from the Heart soundtrack
right after they broke up. Yeah, Coppola thought
the tension would be perfect for the film's theme,
but she declined, said no. Which says a lot about
her prioritizing her own space over a huge career
move. Absolutely. Waits did it with Crystal Gale
instead, but Ricky Lee, she drew a line. Okay,
so she follows this massive debut with Pirates
in 1981, proving she wasn't just a flash in the
pan. Definitely not. Pirates was another critical
and commercial success. Hit number five on the
Billboard 200 went gold. And Rolling Stone loved
it. Five stars, another cover feature. They were
fully on board. And its reputation has only grown.
NPR put it at number 49 on their list of the
150 greatest albums made by women in 2017. It's
considered a classic. But after that success
and dealing with the Waits breakup fallout, she
kind of steps back again. Seems like it. She
moves from New York to San Francisco, becomes
friends with Robin Williams there. Then she puts
out The Girl at her Volcano EP in 83. Mostly
covers, right? And self -produced. Yeah, jazz
and pop standards, plus one original Hey Bub
that was actually left over from the Pirate Sessions.
And then she moves to Paris. For four months,
just to write. Exactly. Which sets up this next
phase, a period of transition, dealing with loss,
pressure, and then finding her way back. Did
that time in Paris, that pressure, shape the
next album, the magazine? in 84. It feels like
it. The magazine co -produced with James Newton
Howard, it's complex. It's got unusual structures
like that three -song suite, Rorschach's. And
musically, it started to shift things. You mentioned
synthesizers. Yeah, minimalist synth patterns,
which is a really interesting signpost. How so?
It wasn't the big 80s synth sound. No, not bombastic.
More textural, atmospheric. It shows her already
leaning towards electronic soundscapes, away
from just the organic jazz band thing. It was
subtle, moody, maybe a bit out of step with mainstream
80s pop, but definitely pointing towards future
experiments. But then after the magazine, she
basically disappears for four years. That's a
long time for someone to air level then. It's
huge, especially in the MTV era. You just didn't
do that. But the reasons were profound. Her father,
Richard, died. And her mentor, Bob Regger, died
in the same year. Wow. Both at once. Yeah. So
this wasn't like a strategic career pause. It
sounds like a necessary retreat. Grieving, processing,
figuring things out, away from the spotlight.
But she wasn't totally inactive. There was that
odd voiceover role. Right. The 1987 animated
film, Pinocchio and the Emperor of the Night,
she replaced Shirley Jones as the fairy godmother.
and sang a song, Love is the Light Inside Your
Heart. The Duchess of Coolsville as the fairy
godmother. That's quite a pivot. It really is.
Shows a range, maybe, or just a willingness to
do unexpected things. Then she starts performing
again, tours Scandinavia, opens for Ray Charles
in Israel. New management with Michael Lang.
Yeah. And this leads to the big comeback. Yes.
The Flying Cowboys' rebirth in 1989. Signed to
Geffen. And the key move here was Gary Gersh
at A &R pairing her with Walter Becker from Steely
Dan to produce. Okay, Walter Becker. That's a
specific sound. Steely Dan is known for that
meticulous, sophisticated, jazzy pop rock. Was
there a risk pairing her with her looser beatnik
image? with someone so polished. It was definitely
a choice, and a risk maybe for her original hardcore
fans. But Becker understood complex harmony,
sophisticated arrangements, and pop structure.
He could give her sound a certain accessibility,
a polish, without totally losing her unique voice
and jazz instincts. In commercially, it worked.
Big time. Flying Cowboys eventually went gold,
and it had two significant singles. Satellites
actually hit number one on the adult contemporary
chart. That's mainstream validation right there.
after being away for so long. Huge. And then
there's The Horses, co -written with Becker.
That song just lives on, doesn't it? It really
does. Kenny Loggins covered it. It was huge in
Jerry Maguire. And Daryl Braithwaite's cover
was a massive number one hit in Australia in
91. It became this kind of global anthem, showed
she could write these incredibly resonant songs.
And this comeback period also brought her second
Grammy. Not directly for Flying Cowboys, though.
Right. First, she got a nomination in 89 for
Best Jazz Vocal Performance Female for her duet
Autumn Leaves with Rob Wasserman on his duets
album. OK, still keeping that jazz connection
strong. Absolutely. And then the win came in
1990 for her duet with Dr. John. Talk about coming
full circle, covering Macon Whoopie. They won
Best Jazz Vocal Performance Duo or Group. So
first Grammy for Best New Artist, bridging pop
and rock. Yeah. Second Grammy firmly in the jazz
world. Exactly. It perfectly underlined her ability
to exist authentically in both worlds or rather
to just ignore the boundaries between them. Which
really sets the stage for the 90s, right, where
the experimentation just goes into overdrive.
Forget commercial expectations. Totally. The
90s start with Pop Pop in 1991. Her first album
of all jazz covers produced by David was. It
felt like a deliberate step away from the polish
of Flying Cowboys. Back to her roots, in a way,
but with a twist. Exactly. It wasn't just playing
standards straight. David Wise gave it this almost
Argentinian flavor, and the song choices were
wild. Tin Pan Alley next to Jimi Hendrix's Up
From the Skies. Hendrix. On a jazz covers album.
Yeah. It was her saying the Great American Songbook
isn't some static museum piece. It includes Hendrix.
It includes everything. She's blending high art
and counterculture freely. How'd that go over?
Commercially, it was quieter on the main charts,
peaked around 121, but it hit number eight on
the contemporary jazz chart. So the jazz audience
recognized what she was doing. And speaking of
unexpected connections, the orb incident. Oh,
yeah. Little Fluffy Clouds, that ambient house
classic from 1990. It's built around these prominent
samples of a Ricky Lee Jones interview. Which
she didn't authorize. Apparently not. Her record
company objected, led to a legal dispute. It's
a funny little footnote, but it highlights that
whole early 90s tension sampling culture versus
artist control. The jazz gentoo is unexpectedly
caught up in the dawn of electronic music sampling.
Her own output kept diversifying, too. Traffic
from Paradise in 93, collaborations, covers.
Yeah, worked with Leo Kotke on that one and famously
covered David Bowie's Rebel. And Bowie loved
it. Said it was his favorite cover of his work,
which is just incredible praise coming from Bowie.
Apparently, she almost. the album boys don't
cry after the cure song which she also considered
covering that album also led to her first live
acoustic record naked songs in 95. right stripped
down versions of her classics no new songs just
focusing on the core songwriting and performance
really showcasing the strength of the material
itself okay now we get to the big one yeah the
most radical shift of the 90s ghosty head in
1997 electronic music monumental leap is right
She worked with Rick Boston on this. And it wasn't
just adding a synth line here or there. We're
talking beats, loops, electronic textures. The
sources specifically connect it to the trip -hop
movement. Trip -hop, like massive attack, poured
his head. Moody, atmospheric, sample -heavy electronica.
Exactly that sound. So imagine going from sophisticated
jazz pop or acoustic songs to that. It was a
complete sonic reinvention. How did people react
to, well, the Duchess of Coolsville? Embracing
Trip Hop. Critically, people admired the sheer
nerve, the artistry. They got that she was pushing
boundaries. But commercially? Right. Yeah, it
struggled. Peaked way down at 159. Which really
underscores her whole approach, doesn't it? Art
first, commerce second. Or maybe third. Absolutely.
She was following her muse, even if it meant
leaving some listeners behind. That artistic
curiosity trumped everything. And then, almost
immediately, another pivot. Back to covers, it's
like this, in 2000. Whiplash, from Trip Hop back
to the Beatles, Steely Dan, Marvin Gaye, Gershwin.
But this time, the covers album approach worked
critically again. It did. Got her seventh Grammy
nomination back in the Best Traditional Pop Vocal
Album category in 2001. It's like she could just
master these completely different styles whenever
she felt like it. We should also mention that
live album from 2001, Live at Red Rocks. There's
a touching story about the cover art. Oh, yeah.
The drawing of the flying horses. It was done
by a young fan who had tragically died in an
accident. Her parents gave the drawing to Ricky
Lee at a show and she decided to use it for the
album cover. A really personal, poignant gesture.
And throughout the 90s and early 2000s, her music
stayed present in films and TV, too. Definitely.
30 -something, Frankie and Johnny, Jerry Maguire,
even House. Her songs just fit certain moods
perfectly. And she kept collaborating Lyle Lovett,
Mellencamp, Kottke again, Arlo Guthrie. Okay,
so that brings us past 2000. Into what feels
like another phase, artistic renaissance maybe.
More overtly political and spiritual themes start
coming through. Yeah, after Ghosty Head and that
burst of activity, she seemed to pull back again
for a bit. Focused on raising her daughter, Charlotte,
tending her garden, just grounding herself. And
that grounding seems to have fueled what came
next. It really feels that way. Because the evening
of my best day in 2003 was musically diverse
jazz, Celtic folk. blues, rock, gospel, all mixed
together. But lyrically, it was incredibly direct.
Her most political album yet. The song Ugly Man,
being the prime example, aimed squarely at the
George W. Bush administration. Squarely. And
she used the music itself as part of the statement.
She talked about using the Black Panther horns
in the arrangement. Referencing Hugh Masakila.
Exactly. Masakila's powerful, urgent, sometimes
dissonant brass sound that was so tied to the
anti -apartheid movement and political struggle.
By invoking that specific sound she wasn't just
singing protest lyrics the music itself was protest
it ends with this call for revolution everywhere
that you're not looking revolution very potent
stuff and the collaborations were still eclectic
mike watt from the minute men playing bass yeah
on the track it takes you there punk rock bass
legend on this jazzy politically charged album
it just perfectly encapsulates her refusal to
stay in one box then came probably her most conceptually
ambitious project The sermon on Exposition Boulevard
in 2007, based on the words of Christ. Yes, it
stemmed from a project by her then -boyfriend,
Lee Cantillon, who had a book called The Words.
The initial idea was maybe having artists recite
the text over music. But she took a completely
different approach. A radical one. The sources
say it had never been done like this. She didn't
just recite. She used the text as a jumping off
point for improvisation, stream of consciousness.
She'd listen to the words and immediately improvise
melody, lyrics, her own impressions right there
in the studio. Wow. So it's not interpretation.
It's almost channeling. Using ancient text as
a prompt for spontaneous creation. Exactly. It's
incredibly vulnerable, incredibly risky. You
risk alienating religious listeners by being
too free, secular listeners by engaging with
the text at all. But the result is this raw,
immediate, utterly unique piece of musical art.
It bypasses traditional songwriting entirely.
Moving into the 2010s, she continued weaving
together personal history and new music, Balm,
in Gilead in 2009. Yeah, that one felt very personal.
Finishing old songs, some dating back to the
mid -80s, like Wild Girl. And it included that
song written by her father. The Moon is Made
of Gold, written by Richard Jones back in 1954.
Her recording, it felt like completing a circle,
connecting back to those deep family roots. And
again, great collaborators. Ben Harper, Alison
Krauss, Vic Chestnut. Then another cover's album,
The Devil. you know, in 2012, produced by Ben
Harper. Right, including her take on Sympathy
for the Devil. And shortly after that, another
big life change. She left L .A. Moved to New
Orleans. Yeah. Settling into the heartland of
American jazz, which you can really hear in her
next album of originals. The Other Side of Desire,
2015. Her first all -new stuff in six years,
steeped in that New Orleans sound. Definitely.
There was even a documentary made about the making
of that album, exploring how the city influenced
the music. She kept the covers coming, too, with
Kicks in 2019, covering Bad Company. Yeah, always
surprising choices. And she played Glastonbury
that year, too, still a major life force. Which
brings us back to Pieces of Treasure in 2023.
The great American songbook album, that eighth
Grammy nomination, still interpreting, still
performing at the highest level. It's an incredible
arc. And alongside the music, there's also been
this consistent thread of activism, of using
her platform. Right, that web community she started
back in 2001, Furniture for the People. Yeah,
explicitly not a fan club, defined as a space
for peace and activism. People discussed gardening,
politics, exchanged bootlegs. It was about engagement.
And this was before her most overtly political
album. So that impulse was always there. Seems
like it. A commitment to connecting her art to
broader social issues. So if we try to wrap our
heads around this whole career, the defining
trait is just refusal to be categorized. The
Grammys alone tell that story. Eight nominations,
two wins. Best New Artist in 80, Best Jazz Vocal
Performance in 90. But the nominations cover
pop, rock, jazz, traditional pop. It's like she
deliberately touched every base just to prove
she could. She doesn't belong to a genre. She
uses genres like tools or maybe costumes like
you said to explore whatever idea fascinates
her at that moment. That ability to move so fluidly
is maybe the ultimate testament to her artistry.
And her memoir Last Chance Texaco really provides
the key to understanding it all. Absolutely.
It connects the life. The troubadour upbringing,
the sudden fame, the retreats, the restlessness
to the art. You see why she's so theatrical,
why she keeps reinventing herself. It all makes
sense through the lens of her life story. It
really brings it full circle back to Peg Lake
Jones, the vaudevillian grandfather. That blend
of performance, music, storytelling. It's been
there all along. Across generations, from the
vaudeville stage to the Venice coffee houses
to the polished pop of flying cowboys, the electronic
experiments of ghosty head, the political statements,
the spiritual improvisations, that restless theatrical
troubadour spirit is the constant thread. So
for you, the listener, what's the big takeaway?
What's her lasting legacy? Well, it makes you
ask. How does someone become the Duchess of Coolsville,
achieve massive fame, and then stay relevant
for five decades without just repeating the formula?
Right. She didn't just keep making Ricky Lee
Jones Part 2, 3, and 4. Not even close. She did
it by retreating when she needed to, by experimenting
constantly, sometimes radically, by embracing
change, even using sacred texts for improvisation.
That complete commitment to artistic exploration
over commercial safety. That's the legacy, the
fearlessness. That's it, the constant self -reinvention.
So if you're exploring her music, don't just
listen to the debut. Put Flying Cowboys on with
that smooth Walter Becker production, then jump
straight to Ghostie Head. Hear the contrast.
That journey across. Stiles is what makes Ricky
Lee Jones truly remarkable.