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.