I have seen several questions similar to this one closed for being too broad, but it certainly seems like an often-enough asked question that I will attempt to narrow the focus down such that it is both answerable and useful.

As an online GM in the past, I have had multiple players apply for my games with Chaotic Evil characters. I never accepted them, for all of the various reasons a GM running a heroic game would be wary of Chaotic Evil, but I have recently begun taking a closer look at the alignment to see if I would be able to craft a Chaotic Evil character capable of working with a heroic party.

As far as I can tell, such a character (not just for myself) would require the following at a minimum:

  • A mature player who understands that this is a team-based game
  • An in-character reason to work with the party
  • The capacity to grow as a character
  • A strong understanding of the differences between "Chaotic Evil" and "Chaotic Stupid"

I would like to allow my players more freedom to choose their alignments in the future, but I cannot guide them through the creation and play of a Chaotic Evil character if I do not know what kinds of challenges they will face.

In your experience, what challenges would a character who fits the above qualifications but is still Chaotic Evil have integrating into a heroic party, while retaining a Chaotic Evil alignment?

To clarify the type of answer I am looking for, I am not asking about whether or not Chaotic Evil could be integrated, or if it should be, or what "Chaotic Evil" means to you. Since those are all opinion-based, please speak from your experiences playing your version of Chaotic Evil, playing alongside another person's version of Chaotic Evil, or GMing a heroic party with at least one Chaotic Evil character in it.

Also, please assume that any interpretation of what "Chaotic Evil" means is valid, assuming it is reasonably south of "Good" and "Lawful". If the game was supposed to be primarily Lawful Evil, such experiences also work just fine from this different angle. Not unappreciated and close enough to be on-topic would be specific examples of how the experience playing, playing with, or GMing for the character was good or could have been improved, but I would ask that these be helpful anecdotes or examples instead of the answer.

On the off chance your answer depends on the system your experience occurred within, please identify the system. Else, I expect most answers to be universal between Pathfinder and the various versions of Dungeons and Dragons, possibly among other games using this alignment system.

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    \$\begingroup\$ If you are voting to close this for being too opinion-based, I would ask that you comment about what parts of the question are opinion-based and how it could be improved. Else, the vote is unhelpful. \$\endgroup\$ Jul 10, 2019 at 2:26
  • \$\begingroup\$ I voted to close this as primarily opinion-based, because what actions and interpretations make up an alignment exceedingly vary table by table. Additionally answering on how to integrate a CE character into a party, exceedingly depends on the party composition, for example trying to add a CE Antipaladin into a party of 3 LG Paladins is going to be different from inserting it into a party of a LG Wizard, LG Rogue, and LG Monk. \$\endgroup\$
    – willuwontu
    Jul 10, 2019 at 2:35
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    \$\begingroup\$ Please review this meta post about how to ask a valid question regarding alignment on this site. I hope that you'll be able to revise this question once you see our boundaries. FWIW,I am not sure that you are asking a question about alignment per se. I think you are asking about how to deal with players who come to the table with varying ideas in their heads regarding what your campaign is based upon, and how much teamwork is the norm for your group. Has your group had a Session Zero yet? What all of your players perceive matters. \$\endgroup\$ Jul 10, 2019 at 2:56
  • 1
    \$\begingroup\$ rpg.meta.stackexchange.com/questions/9262/… \$\endgroup\$ Jul 10, 2019 at 3:21
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    \$\begingroup\$ what is your definition of 'heroic party'? \$\endgroup\$
    – Vylix
    Jul 10, 2019 at 3:58


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