Sith Lord Challenge

Published on August 28, 2019
Last updated on March 6, 2021
Categories: prengubi, slc and starwars

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Draw Your Dark Side

The Sith Lord Challenge, an art contest for everyone, is openly accepting submissions.

How To Enter
  1. Draw your own Sith Lord, defined as "an evil space alien, of any species, possibly wielding a laser sword or psychic powers."
  2. Name your Sith Lord.
  3. Submit your Sith Lord, via email, a comment on this page, a text message, or WebMention. I'll ask whether you want credit.

Sith Lords

  1. Prengubi Cjiiiifgh [created by Maxwell. Pronunciation: "prehng-GOO-bee kyee-ee-ee-eef" or /pɹεᶇ'gubi kji'i:i:if/]

    Prengubi Cjiiiifgh

    Click here for full size.

  2. Darth Prius [created by MU. The name is pronounced "PRY-us" or /'pɹaɪǝs/, not "PREE-us" like the car]

    Darth Prius

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  3. Darth Moba the Hutt™

    Darth Moba the Hutt

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  4. Duglim Hohmschiz (MS-48)

    Duglim Hohmschiz (MS-48)

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  5. Korgoth the World Destroyer [the creator notes that Korgoth is wearing socks and sandals]

    Korgoth the World Destroyer

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  6. Darth Vegtablor [Sith Lord by association of color and taste only]

    Darth Vegtablor

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  7. Sahr Eh Kolpa

    Sahr Eh Kolpa

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  8. Veex


    Click here for full size.

  9. Darth Asshole [created by Jaime]

    Darth Asshole

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  10. Spins the Hypnotist

    Spins the Hypnotist

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  11. Darth Big Boi Maxwell [created by Ruby. Recipient of the Prize for Benighted Dingusry]

    Darth Big Boi Maxwell

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  12. Darth Alley [created by LB]

    Darth Alley

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  13. Darth Patrick Flat-Nuts [created by Larry]

    Darth Patrick Flat-Nuts

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  14. Running Cat-Mask Ski-Sith [created by Mary]

    Running Cat-Mask Ski-Sith

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  15. Dominus Pectus [created by Fedora, of Fedoradventure fame]

    Dominus Pectus

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  16. Darth Lord Kraetertorius [the creator notes that Kraetertorius has an S rank in every stat]

    Darth Lord Kraetertorius

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  17. Darth Dick [his ability to drink all the beer before you arrive is the ultimate evil]

    Darth Dick

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  18. Darth Chef Cat [Recipient of My Aunt's Seal of Approval]

    Darth Chef Cat

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  19. Darth Pthaaargh [the creator reminds would-be foes that Darth Pthaaargh's beefy arms can be used for punching and strangling]

    Darth Pthaaargh

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  20. Khz'zithr Mai'Tzo-Kol [created by E-16Man]

    Khz'zithr Mai'Tzo-Kol

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  21. Unnamed Sith [created by Maddy. A final draft may one day arrive.]

    Unnamed Sith

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  22. Darth Obliti [obliti is a conjugated form of the Latin participle "forgotten"]

    Darth Obliti

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  23. Darth Preta [created by JW, who describes Preta as the ancient revenant of a dead Jedi, who feeds off fallen Sith and Jedi to increase his power]

    Darth Preta

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  24. Saber-Tooth Lion

    Saber-Tooth Lion

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  25. Zim Pi [created by Nicole. She's a Kaminoan and she's angry. Don't be fooled: what appears to be a human nose is actually two Kaminoan nose slits, pierced with a nose ring.]

    Zim Pi

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  26. The Gerblecarp [created by Ian]

    The Gerblecarp

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  27. 3bo [created by Young Master/Mistress Greene]

    Plurt Masberry, Curator of Sith Artifacts and Holocrons at the Cloud City Republican Museum, informs me that this drawing depicts a Sith legend.

    One day 3bo was out on a walk. Then out of the corner of the tree was an evol speiret. So he foght. The evol sprit did not have time to fight back because he die. 3bo finly won his first battol.

    3bo Battles Evol


    Click here for full size.

  28. Darth ASCII [created by gRegor. Recipient of the Digital-Native Sith Ribbon]

    Darth ASCII

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  29. Darth Skivin [created by Aaron]

    Darth Skivin

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  30. Seth, the Ancient Sith [created by Nitzan]

    Seth, the Ancient Sith

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  31. Darth Drongo [created by Chance]

    Darth Drongo

    Click here for full size.

    Darth Drongo's descriptions read as follows:

    • Forehead tat displays drongish deference to his fav classical Terran musician
    • Signature shutter-monocle is attributed abilities ranging from farsight to nigh-omniscience. DD just Likes the Look
    • Effortlessly mastered Forms I-VII in the womb, abandoned his lightsaber by age 12, now simply spams Lemonberry Lightning at all problems
    • Consumes only the finest Twi’lek brews (and bitches)
    • Often goes a-Sithin’ in standard Jedi Knight robe to achieve maximal chaos/comfort despite the contradiction. Absolutes mean nothing to this Sith
    • Founder of galactically-recognized 00F brand apparel, well-known for being mandatory everyday wear in one star sector and banned in another, with the resultant 00Fer wars entirely masterminded by yours truly
  32. Darth Vurm [created by Adam]

    Darth Vurm

    Click here for full size.

  33. Darth Unfinished [created by Spenser]

    Pictures coming soon. This is the first Sith Lord to manifest in 3D; all the previous entries have been drawings. Though sadly incomplete, Darth Unfinished, constructed from chicken wire and papier-mache, represents a significant advance for Sithnology.

  34. Darth Xenon [created by Elissa]

    Look at him go! Huff that noble gas, Darth Xenon.

    Darth Xenon

    Click here for full size.



If you have risen to the Challenge: well done. Thank you for using your imagination at my prompting, and for having the mojo to participate in a public exercise. The creator of Darth Prius deserves a second thanks: he called the Sith Lord Challenge a movement, which makes him the first follower1.

Characteristics of Sith Lords

With help from my colleague, Plurt Masberry2, I've sorted the entries of the Sith Lord Challenge into a taxonomy of Sith characteristics. The five categories are "wizardly," "brutish", "inconceivable," "deceptive," and "artificial."


These Sith eschew the martial lightsaber in favor of a wand or staff which channels terrifying Sith magic. Depictions of wizardly Sith Lords show them either as eerily cheerful, or totally devoid of emotion.

  • Prengubi Cjiiiifgh
  • Duglim Hohmschiz (MS-48)
  • Darth Vegtablor
  • Darth Dick

(If what Khz’zithr Mai’Tzo-Kol wields with its left appendage is a wand, not a lightsaber, then it is "wizardly" too.)


These Sith boast savage appearances, either natural or affected, which strike fear into those who behold them. They typically display black-and-red coloration, spikes, horns, skulls, and other symbols of death and doom. "Brutish" Sith Lords invariably fight with laser swords; they often construct their weapons on unique patterns, or wield them with forgotten techniques.

  • Darth Moba the Hutt
  • Korgoth the World Destroyer
  • Darth Asshole
  • Darth "Big Boi" Maxwell
  • Darth Lord Kraetertorius
  • Darth Pthaaargh (though lacking "brutish" visual features, he is known to savor punching and strangling)
  • Darth Skivin
  • Seth, the Ancient Sith


These Sith belong to alien races from unknown galaxies. Some have peculiar anatomies which prevent them from using Sith laser swords, but none can be prevented from perpetrating cruelties against other life forms.

  • Darth Prius
  • Sahr Eh Kolpa
  • Veex
  • Spins the Hypnotist
  • Darth Patrick Flat-Nuts
  • Darth Pthaaargh (also listed as "brutish")
  • Darth Preta
  • Saber-Tooth Lion
  • The Gerblecarp
  • Darth Vurm


These are humanoids, or members of well-known species, who have turned to the Dark Side. Though they be every bit as deadly as "inconceivable" or "brutish" Sith Lords, they conceal their Dark allegiances with stealth and cunning as they stalk the civilized worlds.

  • Darth Alley
  • Darth Chef Cat
  • Dominus Pectus
  • Darth Obliti
  • Zim Pi
  • 3bo
  • Darth Drongo
  • Darth ASCII (wielding what appears to be a wand, but on closer inspection is undoubtedly a lightsaber)

(The Unnamed Sith appears to be depicted with a lightsaber in the back of her belt, which puts her in this category, too.)


Though Sith droids are shockingly rare, they nevertheless make occasional appearances in Sith histories.

  • Duglim Hohmschiz (MS-48)
  • Khz’zithr Mai’Tzo-Kol



On 2019-08-21, I discovered a crude cartoon of a fox-headed humanoid which I'd doodled a long time ago. I named the creature Prengubi Cjiiiifgh, and decided he was an original Star Wars character.

Fan creations like Prengubi are labeled with the catchall abbrevation "OC", for "Original Content." I've been asking one person after another, "Would you like to see my Sith Lord OC?" If the other person answers in the affirmative, I follow these steps:

  • show them the picture of Prengubi Cjiiiifgh
  • inform the friend that they have been Challenged
  • tell them to draw and name their own character, and show me the results

This plan has worked splendidly.

My Duties

As of 2019-09-03, the Sith Lord Challenge (SLC) has received 20 entries. Ryan Quest has been played by 25-30 people, which means the SLC is now a success on par with that project. Hitting this milestone gave me cause to reflect on the duties I've performed so far as the facilitator of the Sith Lord Challenge.

[2020-04-02: Up to 30 Sith! It's a bright day for the Dark Side.]

  • inventor

    I came up with the idea of the Sith Lord Challenge.

  • web hosting and design

    I set up the SLC page on my website, and edited the homepage to invite people to the challenge. I also went through a few iterations of the page structure, and plan to improve it further by making it possible to link to individual entries.

  • promoter

    As of 2020-04-02, about 1 entry in 5 is submitted by a friends, friends of friends, acquaintances, and strangers. The remaining majority of entries came from my directly initiating others into the Challenge.

  • curator and art coach

    Most of the SLC entries have been accepted as-is, but as of 2019-09-02 I've had cause to reject three initial attempts. These were Darth Asshole, Darth Dick, and the first drawing (Darth Cubious) from the creator of Khz'zithr Mai'Tzo-Kol.

    Each of these entries had a different problem.

    1. Darth Asshole was originally merely a photograph of someone in a skintight "sexy Darth Vader" costume. I gently rebuked the creator, asking him to draw by hand.
    2. Darth Dick was originally submitted as just a head, with no visible characteristics that would make the character on-theme as a Sith Lord. I pointed this out and suggested that the creator make the drawing more elaborate by expanding on Darth Dick's beer-drinking powers.
    3. The short-lived Darth Cubious had had so little effort put into it that I couldn't call it a good-faith submission. I challenged the creator to develop an improved piece while preserving certain characteristics of the original.

    Happily, all three participants accepted my constructive criticism and submitted improved entries, which I admitted to the collection. Well done to you three for sticking with it. You can see in the gallery that the final versions of Darth Asshole and Darth Dick extend their original entries, while the third creator chose to exert more effort on what became Khz'zithr Mai'Tzo-Kol.

  • art editor

    I converted photos to PNG, stripped them of EXIF data, cropped them, and resized them to fit the page. The creator of Darth Lord Kraetertorius originally delivered the drawing and the "character stats" display as separate images, so I merged those together. I also altered Darth Asshole in a way that would never be permitted of an organizer for a serious art competition: I entirely erased the modern-day background of the image. I did this because said background contained everyday items which I felt detracted from the Challenge's fantastic nature.

  • instigator of amateur art

    Some of the entries, including Darth Alley and Darth Moba, were made by people with established credentials as artists, designers, or DIYers. These folks needed no encouragement to participate in the SLC. However, most of the entries (my own included) have been made by people hoping to capture an idea despite limited art skills. To the extent that the SLC is an attempt to stimulate art production in "non-artists," I consider it a rousing success.

Examples from Fiction

Well-known Sith Lords include Darth Vader, Darth Sidious AKA Emperor Palpatine, and Darth Maul. Others include Dooku AKA Darth Tyrannus, Darth Caldoth, Darth Plagueis, and Darth Revan.

Drawings are published here with permission from their original creators. This is an unofficial fan art contest; "Sith", "Sith Lord", "Star Wars", and all related terms are © Disney.
  1. A talk by Derek Sivers on the importance of "first followers." See

  2. Curator for Sith Artifacts and Holocrons, Cloud City Republican Museum.

Maxwell Joslyn's Test Website

GitHub, Email