In the summer of 1997, Lynne Spears brought her then-15-year-old daughter Britney to New York City in order to audition for three record labels in hopes of becoming "the next big thing."
"She came in, warbled 'I Will Always Love You,' and I couldn't wait for it to end," said Michael Caplan, Epic Records vice president of A&R, according to author John Seabrook's "The Song Machine," which explains the process that has created some of the biggest hit songs.
"Her complexion wasn't great, her voice wasn't great ... so we passed," Caplan said.
A team at Mercury Records also passed on Spears, which just left Jive Records, where only a handful of execs liked her demo tape.
"It was in the wrong key," Steve Lunt, an A&R executive for Jive, told Seabrook.
Yet there was one thing that immediately hit the exec and told him to take Spears seriously.
"Britney was trying to sing like Toni Braxton, which was way too low for her. It sounded pretty awful in places," he said. "But when her voice went up high, you could hear the girlish quality, and there was something really appealing about that."
According to Lunt, Spears' demo was accompanied with photos showing a "cute all-American teen in pigtails, sitting on a ramshackle wooden porch in Kentwood [Louisiana], and playing with her dog on the lawn.
"I said, 'This is something we should look at seriously," Lunt recalled.
Spears, wearing a mid-thigh sundress, sang two Whitney Houston songs a cappella for the entire Jive A&R department and Clive Calder, who had recently expanded Jive's success by signing teen-pop boy bands Backstreet Boys and NSYNC.
"Her eyes were rolling back in her head as she was singing and I remember thinking to myself, 'That is really weird but it's going to look great on video,'" Lunt said.
"It was old-school church meets modern-day sex."
As Seabrook notes, Spears' sexy eye roll was simply due to the fact that she was insanely nervous during her audition.
Spears, who was eager and inexpensive to sign, scored a Jive contract that came with a "get-out" clause, meaning the record label could drop her within 90 days.
Spears was immediately relocated to New York City, housed in a Jive penthouse, and groomed to become the American version of Robyn (the Swedish teen-pop queen, who has since redefined herself as a more adult pop singer).
In order to give Spears some direction, Lunt showed her Robyn's music videos, to which Spears responded, "The record is really good, but the video is all wrong. It's in boring black-and-white and no one is dancing.
"If it were me I'd be wearing a miniskirt and I'd be dancing," Spears continued.
As it turns out, Robyn would turn down the opportunity to sing Swedish music producer and songwriter Max Martin's "Hit Me Baby," which was later tweaked to "...Baby One More Time," Spears' debut single that made her an instant superstar.
By the time Martin's demo reached Jive, everyone thought, "Holy shit, this is perfect."
As Seabrook notes:
"Hit Me Baby (One More Time)" is a song about obsession, and it takes all of two seconds to hook you, not once but twice, first with the swung triplet "Da Nah Nah" and then with that alluring growl-purr Britney emits with her first line, "Oh baby bay-bee."
And yet the vocal hook, irresistible as it was, sounded odd. You weren't sure if it was OK to sing it out loud. It's hard to imagine that anyone for whom English is a first language would write the phrase "Hit me baby" without intending it as an allusion to domestic violence or S&M.
That was the furthest thing from the mind of the gentle Swedes, who were only trying to use up-to-the-minute lingo for "Call me."
Spears took initiative in conceiving the video for what would become her big breakout.
According to Seabrook, Spears told veteran video director Nigel Dick, "Let's do a video where I'm a girl in school looking at lots of hot boys."
One of the "hot boys" played Spears' love interest in the video and was actually her cousin and then-Abercrombie & Fitch model Chad Spears.
Britney would also suggest that the girls in the video should wear Catholic-schoolgirl uniforms.
"The outfits looked kind of dorky," Spears remarked. "Let's tie up our shirts and be cute."
The video was shot in LA's Venice High School, the same location used for the 1978 film "Grease."
Spears' debut single sold 500,000 copies on November 3, 1998 — the day it was released.
The song spent 32 weeks on the Hot 100 chart and still remains Spears' longest-charting single, according to Billboard.
In 2011, Spears' high school-set music video was voted by Billboard readers the best of the 1990s and was honored in the final episode of "TRL" as the most-requested video of all time.
See images of Britney Spears throughout the years:
Here's the song that launched Spears' famed career:
More from Business Insider: