Melancholy Baby and Miles on the Phone: Interview with Shirley Horn

In a quiet moment in Bern, Switzerland, legendary jazz pianist and vocalist Shirley Horn sat down to reflect on her early musical journey — one shaped by a deep love of melody, a fearless secret gig, and an unexpected call from Miles Davis that changed everything.

Her path into jazz didn’t begin with singing, but with a young fascination for the piano. Around the age of 12 or 13, Horn recalled being struck by the sound of Erroll Garner.

“I used to play his music by ear, note for note,” she remembered. “I was at school… I guess I got a ‘queen’ [reputation] because I loved his music.”

Although she would go on to become one of the most respected jazz balladeers of her generation, Horn was also a gifted classical pianist. Her parents encouraged her musical education from a young age.

“I started studying at four years old. At 14, I was deep into the classics. That was my love. And jazz came in around 12. But it didn’t interfere — I was studying both, on and off.”

What did her classical teacher make of her jazz explorations?

“There was no problem because I was very good with the classics,” she said. “At the same time I was studying Erroll Garner, I was still working on Bach and Beethoven.”

But it was singing — and performing in public — that marked her true transition from student to artist. And that began with a secret.

“My parents didn’t know I was sneaking out to gigs, so to speak.”

Her first jobs were done quietly, without her family’s knowledge. But one early gig left an impression she’d never forget.

She described playing regularly in a “lovely dining room,” where an older gentleman would come in each night to eat alone.

“He would come in, tip his hat, have dinner alone, and go. This went on for about six weeks, getting close to Christmas.”

Then, one evening, he arrived carrying a striking gift.

“He had this gorgeous, great big turquoise teddy bear. He said, ‘Now, if you sing Melancholy Baby, the teddy bear is yours.’ And I sang Melancholy Baby.”

She kept that bear for years.

Horn’s career, however, wouldn’t remain a secret for long.

Her first album found its way into the hands of Miles Davis — who famously had a deep appreciation for vocalists who understood space, tone, and restraint.

One morning, Horn was eating breakfast at her mother-in-law’s house when the phone rang.

“He said, ‘This is Miles Davis. I want you to come to New York.’”

She thought it was a prank — a friend playing a joke. But it wasn’t.

“I told my husband, ‘Maybe I should go to New York.’ So I left Virginia, went to Washington (my hometown), packed a bag, and went.”

When she arrived at Miles Davis’ home, any lingering doubts disappeared.

“His kids were singing songs from my first album,” she recalled, still visibly amused. “It was all true.”

Soon after, she found herself opposite Davis on a bill at the Village Vanguard, thanks to Max Gordon, the legendary club’s owner. Though she didn’t perform directly with Miles, her trio played during the same engagement.

“Of course, I sat in sometimes — when I wasn’t scared!” she laughed. “Wynton Kelly used to make me play. I was real nervous, but it was fun. Great fun.”

Shirley Horn’s rise was never built on noise or hype. It was carved quietly, through years of classical study, instinctive playing, and the kind of personal storytelling that captivated Miles Davis himself.

And as she tells it, it all began with a turquoise teddy bear and a heartfelt version of Melancholy Baby.

Watch the full interview here:

From sneaking out to early gigs without her parents’ knowledge to being personally invited to New York by Miles, Horn’s journey was defined by subtle defiance, slow-burning brilliance, and a deep respect for the music itself. She didn’t chase the spotlight — but when it found her, she was ready.