Anyone who's familiar with Star Wars knows of the Sith, the order of Force users who stood opposite the Jedi and wielded the power of the Dark Side. Existing in secret and standing at only two members at a time, Master and Apprentice, they waited patiently for a thousand years for the opportunity to take hold of the galaxy and destroy their enemies, the Jedi. A plan that was finalized through the manipulations of Darth Sidious, better known as Emperor Palpatine, as seen in the events of the Star Wars prequel trilogy.
But the Sith obviously didn't begin with Sidious, given how long they waited. In fact, the Sith Order itself goes back even further than the thousand years before Episode I when they were thought to have become extinct, and even originally didn't belong to a sect of Dark Side users. The name “Sith” originally first belonged to a race of red-skinned humanoids that existed on the planets Korriban and Ziost over 130,000 years before the first Star Wars film (or BBY, Before the Battle of Yavin). The race was eventually conquered by a group of Dark Jedi who had been banished by the Jedi Order nearly 7,000 years BBY, and the Sith as a species soon ceased to exist with the name being applied to the sect of Dark Side users. There have been many factions over the years, such as the Sith Empire with members in the legion, to the Darth Bane's Order of the Sith Lords that only held two members at a time, but would all be ruled by the most powerful of them, known as the Dark Lord of the Sith.
Naturally, numerous Sith Lords have existed over their millenia-long history, but only a select few truly stand out. Here is a list of those Sith Lords and how they helped mold the Sith into how many know it, as well as guide it into the future beyond the movies and current timeline.
Xoxaan
One of the first Sith Lords, XoXaan was part of the group of Dark Jedi who first conquered the original Sith race following their banishment and discovery of the then unknown planets of Korriban and Ziost. Very little is known about her, but her status as one of the first Sith Lords makes her important. In addition, she would also play a major role in the future of the Sith. 7,000 years later, her holocron was found on Korriban by former Jedi A'Sharad Hett, allowing XoXaan to teach him the ways of the Sith and transform him into Darth Krayt. Unfortunately for Krayt and his Sith Order, nothing in her teachings could help save him from the Yuuzhan Vong organisms that were taking over his body.
Naga Sadow
Naga Sadow was a powerful Sith Lord who was part of the first Sith Empire, existing over 5,000 BBY. He sought to become the new Dark Lord following the death of Marka Ragnos, competing with his rival, Ludo Kressh. After sibling hyperspace mappers Gav and Jori Daragon appeared in Sith space, Sadow used his fellow Sith Lords' fear of the Republic to take the title of Dark Lord and invade the Republic to begin the Great Hyperspace War. However, the Sith were defeated thanks to the efforts of the Jedi and their allies, as well as Ludo Kressh's treachery, and the Sith Empire was destroyed. Sadow, however, survived and was stranded on the moon of Yavin 4, where he waited for his chance to rebuild the Empire but dying before his plans could be realized. Entombed on Yavin 4, Sadow's spirit was resurrected by Freedon Nadd 600 years later, then destroyed after Nadd learned the ways of the Sith from Sadow's spirit.
By invading the Old Republic and starting the war, Naga Sadow was responsible for introducing the Sith to the Republic and to the Jedi, who at that point believed the Sith to be nothing more than a myth. More importantly, it was during his exile that he built a great Sith temple that would, millenia later, be used by the Rebel Alliance as a base during the events of “Episode IV: A New Hope”. That same temple, in a great twist of irony, would be later used by Luke Skywalker as the site of his Jedi Academy to rebuild the Jedi Order until its destruction at the hands of the Yuuzhan Vong.
Freedon Nadd
: Freedon Nadd was a human Sith Lord who existed 4,400 years BBY. A former Jedi Knight, Nadd served the Galactic Republic until he fell to the Dark Side and left the Jedi Order. He eventually found his way to Yavin 4 and Naga Sadow's temple, where he resurrected and apprenticed himself to Sadow's spirit. After learning all he could, Nadd destroyed Sadow and became the new Dark Lord of the Sith. He conquered the planet Onderon, ruling it as king until his death. His spirit continued to teach the ways of the Dark Side to his descendants, until it was finally destroyed by fallen Jedi Exar Kun, who did so after learning all he could from Nadd, just as Nadd did to the spirit of Naga Sadow.