Off the top of my head, I believe the singer-songwriter era began in the 50s with the early Rock 'n Roll pioneers mentioned above. A lot of reasons for this. First of all, popular music in the first half of the 20th century was far more formalized. Record companies hired writers, then handed the compositions to musical arrangers, then finally over to professional musicians to record each song. It was a complex production, involving an assembly line of expertise. A hit record started in the minds of Rodgers & Hammerstein, was broken down into a score by Nelson Riddle, recorded by session musicians, and sung by Frank Sinatra.
Chances of having one person who could do everything – including sing the song – was slim. Chance of a record company giving one person so much control was zero.
A small number of big band leaders wrote their own songs, but Duke Ellington and Count Basie were the exceptions, and of course they hired their own singers.
There were early 20th century jazz/blues artists who wrote and recorded their own music, but while the songs were great, the performances were muted and small. Nobody was getting up to dance, nobody was swooning, so no company was investing big money.
Rock 'n roll was the perfect storm to showcase a wider scope of individual talent to a wider audience. It was exciting and fresh, and most important: it was simple. You just needed four or five guys, and you DIDN'T need music charts or training. Just play the blues, but faster and with an electric guitar. Chuck Berry, Little Richard, Jerry Lee Lewis were coming up with great tunes, and were also developing their own style of performing. Anyone could play Johnny B Good or Tutti Frutti, but nobody could perform them like the original artists.
The Beatles took songwriting-performing to a new level. Their songs were better, they had cute accents, and they were white. All the above allowed them to crossover into almost every radio station in every country, where they could perform in every club – luxuries the mostly-black pioneers of the 1950s were never permitted.
I'm sure I'm forgetting a ton of stuff – didn't even mention Ray Charles! – but the point is that singer-songwriters found a path to success once the recipe for making hits changed. Turns out you don't need an orchestra and arrangement to get a crowd's pulse racing. All you need is a simple idea, and drums, bass, and electric guitar to give it a beat.
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