puckish (adj)
Mischievous in a playful way; impish
Promethean (adj)
Daringly original or creative; life-enhancing
Pollyanna
An excessively optimistic person
Mickey Mouse
Cheaply made; trivial or petty; useless or insignificant
maverick (n)
An independent thinker; someone who refuses to conform to accepted views
quixotic
Impractical; impulsive; tending to have a romanticized view of life
Pyrrhic victory
A win that has such high cost, it is basically the same as a defeat
Sword of Damocles
An immediate doom that is out of your control
Curmudgeon (noun)
a bad-tempered, disagreeable, or stubborn person
Machiavellian
Using clever trickery, amoral methods, and expediency to achieve a goal, esp. in politics
Kafkaesque
Overly complex and seemingly pointless, impersonal in an often disturbing way
prig (n)
A person who is overly concerned with petty matters; someone who acts morally superior to others because of good behavior
guru
A spiritual guide or religious leader, especially of Eastern religions; an influential expert
mensch
A good, kind, honorable person
yenta
A match-maker; a gossipy woman
Doppelganger
A ghost; a person who looks just like you; a double
emeritus
Retired but retaining a professional title
Gordian Knot
An impossibly complicated situation
nabob
A wealthy, prominent person
ombudsman
An official who investigates complaints between people and the government