User blog comment:JKGame/Nate, Francis, and Teddy vs The Cutie Mark Crusaders: My Little Rap Battles/@comment-34129479-20180807042200

This is probably the best of the series so far, had a nice flow to it! The Cutie Mark Crusaders took it! ^_^

Princess Ember vs Vladimir Putin

Henry Stickmin vs Dick Figures

Stanley Yelnats vs Dig Dug

Randy Marsh vs Bob Belcher (Bob's Burgers) or Richard Watterson (Amazing World of Gumball)

Notch vs Hideo Kojima

Kylo Ren vs Ren Hoek (Ren & Stimpy) or Bowser Jr. or Reaper (Overwatch)

As for the hint; I believe "The Discoverer of the Lost Empire" is implying Milo from Disney's Atlantis, and I believe the "Not Twilight or Moondancer" awkward nerd is Sunburst.