ComplexCon returns to Long Beach Nov. 6 - 7 with hosts J. Balvin and Kristen Noel Crawley, performances by A$AP Rocky and Turnstile, and more shopping and drops.

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There has been a lot of talk about the generational divide between young hip-hop artists and their older counterparts over the last couple of years. Despite lingering misunderstandings, some veteran producers like Timbaland have reached across the chasm and started collaborating with young artists like Ski Mask The Slump God and 6lack. These collaborations can pass insights along to new artists and breathe new creative energy into older producers. This made us think: What other cross-generational collaborations would we like to see? How would someone like Trippie Redd sound rapping over a DJ Premier beat? What would Noname and Q-Tip come up with in the studio together? All these young artists are doing great on their own, of course, and none of them need to collaborate with older producers—but we can't resist fantasizing about the possibilities. These are ten cross-generational rap pairings we'd love to hear.

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