Raynoma Gordy Singleton: Miss Ray's 5,000 Bootleg Copies of My Guy

SPEAKER_1 (0:00)

Picture this, it's the mid-1960s, and we're looking at this incredibly audacious crime in the music industry.

SPEAKER_2 (0:07)

Oh, right, the bootleg.

SPEAKER_1 (0:08)

Exactly. Someone has just illicitly pressed, like, 5,000 bootleg copies of the massive hit song, My Guy, by Mary Wells.

SPEAKER_2 (0:17)

Which was huge at the time.

SPEAKER_1 (0:18)

Oh, massive. And they bypassed the distributors, they dodged the official royalty channels, and they sell these records on the sly.

And it's strictly to generate this desperate injection of cold hard cash to keep a struggling New York City office afloat.

SPEAKER_2 (0:32)

You know, when you hear a set up like that, I mean, it sounds like a plot pulled straight from some gritty music business mob movie.

SPEAKER_1 (0:38)

Right.

SPEAKER_2 (0:38)

Your immediate assumption is that the culprit was, I don't know, some cutthroat rival label executive, or maybe a local organized crime syndicate just trying to skim off the top of a smash hit.

SPEAKER_1 (0:48)

Well, the reality is actually far more compelling. Because the bootlegger wasn't a mobster, and it wasn't a rival either. It was one of the foundational creators of the very record label that owned the song. I mean, she was bootlegging her own company's hit just to keep her own publishing division running.

SPEAKER_2 (1:04)

It's wild.

SPEAKER_1 (1:05)

It really is. So welcome to the Deep Dive. Today, our mission is to unpack this fascinating stack of sources, including historical records and biographical data, to explore the life of a woman named Raynoma Mayberry, Liles Gordy Singleton, or as those in the know call her, simply, Miss Ray.

SPEAKER_2 (1:23)

And it's a really critical story for us to analyze because when you look at the history of this particular musical empire, I mean, the narrative is just overwhelmingly dominated by a handful of legendary men.

SPEAKER_1 (1:35)

Right. We're talking about Motown.

SPEAKER_2 (1:36)

Exactly. Motown. And the established history often just defaults to the male founders. You know, it treats the women involved as like muses or just assistants.

SPEAKER_1 (1:46)

Which is exactly why we're bypassing those well-worn legends today. We're giving you the original narrative of a brilliant woman whose musical literacy, her incredibly sharp business acumen, and honestly, her sheer unfiltered survival instincts poured the very concrete foundation of that legendary music empire.

SPEAKER_2 (2:04)

Absolutely.

SPEAKER_1 (2:05)

But to understand how Ms. Ray did it, we kind of have to start in Detroit. She was born Raynoma Mayberry in March of 1937

And her family dynamic right away sets up this interesting foundation.

SPEAKER_2 (2:17)

Right. She was her mother, Lucille's eighth child.

SPEAKER_1 (2:20)

Yeah. But her father, Ashby Mayberry's first.

SPEAKER_2 (2:23)

And that background really provides the context for the environment she was raised in. Her father, Ashby, worked as a janitor for Cadillac.

SPEAKER_1 (2:30)

Which in today's economy, you know, we might not associate that job title with significant upward mobility. Right.

SPEAKER_2 (2:37)

But in the booming Detroit automotive economy of the mid-20th century, that was a solid union job. He provided a very stable middle class life for the family.

SPEAKER_1 (2:45)

Yeah, the sources specifically note he did well enough to buy a home on Blaine Street, which was situated in this primarily Jewish neighborhood in Detroit. So as a listener, you can picture this environment of relative stability.

SPEAKER_2 (2:56)

But it doesn't last.

SPEAKER_1 (2:58)

No, it doesn't. As she gets into her early 20s, that stability just vanishes. In the mid-1950s, she meets and marries this aspiring musician named Charles Liles.

SPEAKER_2 (3:08)

Then in December of 1955, they have a son together, Cliff.

SPEAKER_1 (3:11)

Right.

SPEAKER_2 (3:12)

And this is really where the harsh realities of the music business first hit her. Because trying to make a living in music while raising a newborn, it creates severe financial pressure.

SPEAKER_1 (3:22)

Oh, I can only imagine.

SPEAKER_2 (3:23)

Yeah. And the marriage just collapses under the weight of it, leaving her to navigate the world as a single mother. That desperation to provide, you'll see, is a recurring theme that drives for most pivotal decisions.

SPEAKER_1 (3:34)

Which actually brings us to the moment that literally changes music history. It's 1958

Raynoma and her younger sister, as well as, they decide to go audition as a singing duo.

SPEAKER_2 (3:44)

Right.

SPEAKER_1 (3:44)

And the person sitting across from them, judging this audition, is a young, relatively unknown songwriter around Detroit named Berry Gordy.

SPEAKER_2 (3:51)

And Gordy is just not impressed. I mean, he listens to them sing, and he just isn't feeling the vocals. It's basically a flat rejection.

SPEAKER_1 (4:00)

Right. And normally, in any biography, that's where the story ends. You audition, you fail, you go home.