The 1990s were huge for hip-hop. The genre transformed and evolved throughout the decade, growing for the better and creating new stars almost yearly. At the end, in 1999, hip-hop was stronger than ever, while also showing that the future would be in good hands.

Hip-hop has always been interconnected, with 1999 putting that fact on full display. Jay-Z dropped "Jigga My Nigga," the Swizz Beatz-produced anthem which originally appeared on the Ruff Ryders compilation, Ryde or Die Vol. 1. In the same era. Ruff Ryders frontman DMX was continuing his hot streak with "What's My Name" dominating the charts, radio and speakers all over the U.S. At the same time, the first lady of Ruff Ryders, Eve, was making a name for herself with the sweet and playful "Gotta Man," which also featured production from Swizz. The Ruff Ryders had it locked from all angles, whether it was their relationships with other rappers or the talent they had in-house.

With that said, 1999 wasn't all about singular rap crews dominating; there were some new faces who would begin their run here. Eminem's quirky "My Name Is" came out this year—who knew the scrawny bleach blonde kid from Detroit would go on to become a living legend? Ja Rule, the star of Irv Gotti's newly minted Murder Inc., dropped "Holla Holla" and never looked back, racking up platinum plaques and Billboard hits soon after.

Even with East Coast hip-hop's dominance being covered ad nauseam, you still can't forget about the South. New Orleans' own Cash Money Records was already doing its thing, but future superstar Lil Wayne was still a young kid. It became clear the lil guy could go with the best of them after his single "Tha Block Is Hot" hit the airwaves. Even back then, Wayne was technically sound, clever and confident. In the clubs, Pastor Troy's "No Mo Play In GA" was a staple—it influenced the sound of Atlanta hip-hop both then and now. Troy's track proved to be timeless, ringing off in the right crowds up to this very day.

Hip-hop was well on it's way to becoming the biggest genre in the world. The way hip-hop closed out the 1990s was proof that it would never die. It simply couldn't be stopped. Different interpretations of the art form and the infusion of youth into it back then allowed it to live on now. Every rap fan should be thankful for what took place in 1999. Listen to the hip-hop songs turning 20 below.

  • "Big Pimpin"

    Jay-Z Featuring UGK
  • "Bling Bling"

  • "Breaker, Breaker"

  • "Da Rockwilder"

    Method Man and Redman
  • "Dead Wrong"

    The Notorious B.I.G. Featuring Eminem
  • "Do It Again"

    Jay-Z Featuring Beanie Sigel and Amil
  • "Down Bottom"

    Drag-On Featuring Juvenile
  • "Full Clip"

    Gang Starr
  • "Gotta Man"

  • "Got Your Money"

    Ol' Dirty Bastard Featuring Kelis
  • "Hate Me Now"

    Nas featuring Puff Daddy
  • "Hip Hop"

    Dead Prez
  • "Holla Holla"

    Ja Rule
  • "Hot Boyz"

    Missy Elliott Featuring Nas, Q-Tip, Nicole Wray and Eve
  • "How To Rob"

    50 Cent Featuring The Madd Rapper
  • "Ill Bomb"

    Funkmaster Flex and Big Kap Featuring LL Cool J
  • "It's Mine"

    Mobb Deep Featuring Nas
  • "I Want It All"

    Warren G Featuring Mack 10
  • "Jigga My Nigga"

  • "Love Is Blind"

  • "Memph Bleek Is..."

    Memphis Bleek
  • "Ms. Fat Booty"

    Mos Def
  • "My Name Is"

  • "Nastradamus"

  • "No Mo Play In GA"

    Pastor Troy
  • "No Pigeons"

    Sporty Thievz
  • "Play Around"

    Lil' Cease Featuring Lil' Kim
  • "Quiet Storm"

    Mobb Deep
  • "Simon Says"

    Pharoahe Monch
  • "Symphony 2000"

    EPMD Featuring Redman, Method Man and Lady Luck
  • "Tha Block Is Hot"

    Lil Wayne
  • "The Next Episode"

    Dr. Dre Featuring Snoop Dogg, Kurupt and Nate Dogg
  • "Vivrant Thing"

  • "Watch Out Now"

    The Beatnuts
  • "What's My Name?"

  • "Who Dat"

    JT Money Featuring Solé
  • "Wild Wild West"

    Will Smith Featuring Dru Hill and Kool Moe Dee
  • "Xxplosive"

    Dr. Dre Featuring Hittman, Kurupt, Nate Dogg and Six Two
  • "You Can Do It"

    Ice Cube
  • "You Got Me"

    The Roots Featuring Erykah Badu

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