It may seem hard to believe now, but 20 years ago, the idea of Jennifer Lopez, the recording artist, was something of a gamble.

Back in 1999, the In Living Color Fly Girl-turned movie star was coming off of hits like Selena, Anaconda and Out of Sight. She'd become the first Latin actress to earn over $1 million for a film. She had undeniable momentum—momentum that could be derailed temporarily, if not for good, should a foray into music turn out to be nothing more than an ill-advised vanity project, an embarrassing detour away from what had been proven to work. Sure, she'd sung in Selena, but those songs weren't hers and everyone knows that playing a pop star isn't the same as becoming one.

And yet, she forged on anyway and when On the 6, her debut album, arrived on June 1, 1999, the world learned a lesson they'd be reminded of time and time again over the last two decades: It's never wise to bet against Jennifer Lopez.

"The idea to do an album is not a gimmick," Lopez told The Los Angeles Times on the eve of On the 6's release in 1999. "It wasn't, 'Oh, I'm doing good as an actress, maybe I should make an album!' I had a record deal [with Giant Records] before my movie career, luckily enough, took off. When I did 'Selena,' it all came back again, having that interaction with the fans and the public, which you don't get in movies. I missed that very much. I missed the excitement of the stage, which I had early in my career with the musical theater."

When she finished filming the 1997 biopic, which told the story of slain Tejano singer Selena Quintanilla, she decided to record a demo which would go on to start a bidding war between Sony and EMI Latin. (It didn't hurt that the wave of Latin Pop was beginning, thanks to Ricky Martin and Marc Anthony breaking through.) Jeff Ayeroff, who was the head of Sony subsidiary label the Work Group at the time, wanted to sign her. And he wasn't afraid to call in the big muscle to get what he wanted.

Jennifer Lopez, Tommy Mottola, 1999

Richard Corkery/NY Daily News Archive via Getty Images

"We had to go to Tommy [Mottola] because it's [such a big deal], and Tommy takes her under his wing," he told The L.A. Times at the time, revealing that the then-head of Sony Records himself OK'd the deal.

Mottola, who'd launched the careers of Céline Dion and his former wife Mariah Carey, as well as helping Gloria Estefan break into American markets, tells us there was never any doubt about what Lopez was capable of. "When I first met her in my office, she had just begun doing a couple of movies but I knew that she was going to be a triple threat," he recalled to E! News exclusively during a recent phone call. "It was clear and obvious to me from watching her start with The Fly Girls and hearing her demos – this was before she ever made a record."

Of course, being certain is one thing. Everyone's certain in this industry until they're not. Once Lopez signed with Sony, it became time for the starmaker to put his money where his mouth was. "We worked really hard on that album and creating that first album," Mottola told us, revealing the extreme lengths he went to make sure there wasn't a single false step in Lopez's debut era. "We even did some screen tests with some video because we believed in her so much, I believed in her so much. We shot multiple covers until we got the right one. So there was a tremendous amount of work that went in and even some trial and error things – doing videos and tests, covers and getting it all right to try to make, first of all the right music that really was you know the most important thing and then of course all the imaging that went along with it. And we paid you know, really strict attention to detail."

Not everyone in Lopez's circle was so convinced from the jump that this was the right decision for her. As her longtime manager Benny Medina, who'd only been working with his client for 18 months by that point, told The L.A. Times back in '99, he was one of them. "I was initially concerned with her getting involved with music because when you've had so much integrity in one area, it's important that you be a little cautious about doing something that could potentially erode that," he admitted. "But the music convinced me."

When asked how he and Lopez settled on the sound that would make her a superstar, Mottola told us it all came down to one thing: Their shared beloved home, the Bronx. "We were those kids from The Bronx, right? And of course hip-hopop was ruling and she grew up with it and we were ruling the world with it at Sony at the time and so we wanted to make it pop but yet it had to have that hip-hop element because of her ethnic background and coming from the streets of The Bronx and growing up with that music," he explained. "It was part of her life, part of her world and part of what occupied all of radio at that time. So we really wanted to have a fine line of a mixture of that plus pop songs that we've heard that could breakthrough not only on cross over radio but also that could have breakthrough in dance, clubs and internationally."

For that pivotal first single, the song that would really be the make-or-break moment in this whole endeavor, he turned to a proven heavyweight at that time, producer Rodney "Darkchild" Jerkins. "Tommy Mottola called me and was like 'Listen I have this young actress that we believe is going to be a superstar and we're getting ready to launch her music career and we'd love for you to produce and write her first single,'" Jerkins told us over the phone. "He had me go into his office and played me a couple of things and I was like 'I get it, I got it, put me in the studio.' And "If You Had My Love" came out." 

For Jerkins, what stood out about this untested aspiring pop star upon first working with her was an unparalleled work ethic. "If someone has a career that spans decades, there's a reason for it, right?" he said. "And first reason, I believe, is the work ethic...The way she was and her work ethic, even in the studio and wanting to give the best, her all and all, on this record. She connected with "If You Had My Love" in a way, she loved it. She worked hard and she knew that this could be that big moment, that breakthrough moment for her as an artist...If you get that part right, a lot of other things come with it."

Rodney Jerkins

Paul Morigi/WireImage for The Recording Academy

It didn't hurt that Jerkins had written a killer track. One that, if you'll believe the internet, Michael Jackson was also interested in recording. Although, the producer told us that Wikipedia's version of events isn't exactly the truth. Close to it, though. "What happened was, first I did the track. Michael Jackson just so happened to be in the office the next day when I sent it in. They played the track for Michael, and he was like 'Oh this is an interesting track.' He didn't want it for himself, more so saying this an interesting track, 'Not for me, but this is a really good track.' So he liked what he heard and that's what happened." A good sign, to be sure.

"Once she actually recorded the record, it's one thing—you know, you don't know what you're getting until it's done," he continued. "So once everybody heard the record [and] it was complete, she was super excited, super happy, as well as everyone on board. We all knew that it was something. You don't know what a hit record is but you do have a feeling with certain songs because they move you in a kinda certain way. This was one of those songs that everybody was wowed by."

That went for the listeners at home, too. The track was released a month ahead of the album, on May 4. It peaked at No. 1 for five weeks and became one of the best-selling singles of 1999, selling over 1.2 million units in the United States alone. "The first thing was a homerun," Jerkins reminisced. "Sometimes you come into the music industry and you gotta get warm before you get hot. She came in all hot, all fire…You just have to really follow up and keep your brand moving."

Mottola assembled a team of powerhouse producers to work on filling out the rest of the album. Cory Rooney, who'd worked with Carey, Destiny's Child, and Jessica Simpson, was brought in for a meeting where he and Lopez bonded quickly. "I sat down at the piano and sang a song called 'Talk About Us,' and she and Tommy loved it," he told SongwriterUniverse.com in 2003. "We recorded that song the next day." He went on to become the album's co-executive producer, working on six songs altogether.  Estefan and husband Emilio Estefan, Jr. gave her the track "Let's Get Loud," with the latter going on to produce a few more tracks. Future boyfriend Sean "Puffy" Combs contributed a track. And, conscious of her Puerto Rican heritage, Mottola had one more box to tick.

Jennifer Lopez, On the 6, album cover

"I made sure that she had the ultimate duet on that album which we did in Spanish and we did two of the other songs that were on the album in Spanish as well, but the duet was a duet with Marc Anthony," Mottola said, referencing "No Me Ames," which she recorded with her future ex-husband. "It was instant credibility."

"When I went into that studio to make this album, in my head I knew what it was going to be," Lopez told The L.A. Times in '99. "I knew the kind of music that moved me and what I wanted to make and what I wanted to try, and the elements that I wanted to incorporate for it to be Jennifer Lopez's music."

As Jerkins—who wrote a second track on the album, "It's Not That Serious," inside Whitney Houston's guest house, which he'd rented for the month—told us, she was immediately aware of the perfect alchemy that is her sound and has never abandoned it. "What Jennifer's uniqueness was [is] simplicity, emotional, dance. Those three terms define the music elements that I would say is all her. Keep it simple, for everyone to sing along, still be emotional lyrically, conversationally and the 'I still wanna dance,'" he admitted. "She's the leader of the pack, her voice is very clear and loud [with] what she wants. To this day, she would text me or call me saying 'I need this' like she knows what she wants. It was really clear and 99.9 percent of the time it's those three things that I just told you. You know 'I need something emotional. I need something that I could dance to.  But simple, really simple.' Those three things kept the balance.

"If you look at her career musically, she knew how to embrace hip-hop, she knew how to embrace the Latin, she knew how to embrace dance music and the magic that she had was that she was able to take all these different genres and blend them," he continued, "and it became her thing."

When On the 6 debuted on June 1, 1999, it did so at No. 8 on the Billboard 200, surprising those who were aware of what a risk it posed. It was the No. 50 best-selling album of the year, positioning her on a global superstar track that wouldn't have even been possible if she'd just remained in her movie star lane. She's released seven studio albums since, become a powerhouse TV producer, had a lucrative three-year residency in Las Vegas, and is just now preparing to embark on her first concert tour in seven years to celebrate her upcoming 50th birthday. And throughout it all, the songs that helped launch this enviable career have remained some of the most beloved in her discography. (Find us a person who doesn't turn up when "Waiting for Tonight" come on and we'll find you a liar.)

As for why, Mottola has a theory. "I think [because] they were all big hits right out of the box," he told us. "I mean "Let's Get Loud" is like an anthem at sports events. You don't go anywhere without hearing that, right? [Also,] I think rising to the top of superstardom which is very rare these days, cause there's not a lot of superstars being made anymore, but she broke through and her rise just kept happening. She's bigger now than she ever was. It sheds more light on those hits as milestones and things that will always resonate."

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