2. General Chang - Star Trek VI: The Undiscovered Country
General Chang almost won. He was on the verge of taking over the Klingon Empire, bringing war to the Federation border, and killing James T. Kirk. Essentially, he was set to be the truest warlord of warlords. Yet, he failed. By happenstance more than anything else. He had Kirk tried for his crimes against the Klingon empire, and had him stuck away in a mining colony he had no chance of escaping. Had the near-impossible not happened, Kirk, surviving his escape, Chang would've won. Instead, Kirk was able to rise to the occasion and end Chang once and for all. He's not as quotable as Khan but he's better than Khan in every single way after, including his look. Khan looked cool, but Chang looked proven. His eye patch bolted to his face, a testament that he was tougher than Khan could ever hope to be.
1. The Borg Queen - Star Trek: First Contact
Now, she's not the most quotable villain out there, but everything else she does is perfect. Unlike every other character on this list, The Borg Queen wins. After Starfleet engages the Borg near Earth, the Borg are able to send the Queen and a detachment of drones back in time to assimilate the Earth. The crew of the Enterprise-E watches it happen in real-time, watching Earth be taken over by the Borg, dooming the Alpha Quadrant. Their only hope is to go back in time and stop the Borg Queen from doing just that. In their quest to stop her, hundreds if not thousands of lives on Earth and the Enterprise-E are lost. The Borg Queen nearly corrupts Data and is about to have the entire Enterprise blown up, if it wasn't for Data snapping out of the Queen's grip and killing her. She was so close to winning. When you're that close, you're obviously the best.