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1 - Exar Kun
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Kun was a Jedi that just wanted to get stronger and stronger. So much he left the order in pursuit of forbidden teachings. No doubt he achieved becoming stronger as he wished.
He entered the tomb of previous discussed Sith Lord Freedon Nadd, that taught him everything he knew and got killed afterwards. Exar Kun later traveled to Yavin 4 where he amassed even more power.
He killed entire Sith Cults that he thought were too powerful for his liking. He stole a very ancient Sith Holochron which he used to get again more power and turn many Jedi Padawans - convinced then to kill their masters.
Exar Kun later went and killed the supreme chancellor and he dueled the grand master of the Jedi Order, which was no match for him.
The foundations of a well established Sith Empire were laid.
When he was attacked by the traitor Ulic Qel-Droma and his thousands of troops he separated his body from his spirit. Nomi Sunrider and thousands and thousands of Jedi managed to incarcerate Exar Kun in a temple forever.
But forever is a long time, and when Luke was already the grand master of a new Jedi Order, he tried to turn his students, killing one in the process. He separated Luke's body from soul too but got defeated by the combined power of all of Luke's students.
2. Darth Revan
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Revan is my favorite character, he was a Jedi that during the Mandalorian invasions desired to protect the countless lives on the outer rim, but the council didn't let him or any Jedi intervene in the war. So Revan, with the best diplomatic abilities and leadership virtues of all the saga, mustered an enormous number of Jedi to go fight with him, disobeying the council. His padawan Malak followed him and that grouped won the war for the republic.
But they didn't return... they found a star forge able to produce an immense fleet and give them power so they became sith. Darth Revan as the Lord of the Sith and Malak as his apprentice.
Raven was also known as a really powerful Sith Lord, able to turn Jedi at will, and to get allies from everywhere.
He was captured by the Jedi and brainwashed, then beeing converted to the light side. As a Jedi, the third most powerful Jedi ever, he defeated his apprentice now dark lord Malak and was declared as the Hero of the Republic
3 - Darth Vitiate
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Darth Vitiate killed of an entire planet including numerous Sith Lords and absorbed all their power, he became immortal and killed his father with just a tought.
He bested Revan once and he, well again, became Immortal - almost... he passed away MILLENIUMS after his birth.
Darth Plagueis had him as his muse and envied his knowledge and he was the sith lord who reigned for most time.
4. Darth Maul
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Soloed both obi-won and he master.
5. Darth Vader
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