Thanks to everyone who participated I now have 5 quotes and occupations. There's a tie between the American Writer and the Post Office Aviator, between Hemmingway and St Exupéry. Only one way to sort it out, FIGHT!

The post office aviator wins, by dint of not shooting himself.

1- Russian Emigré
2- Left Bank Intellectual
3- Post-Office Aviator
4- Defrocked priest
5- Disenchanted Anarchist

No place for Montessori, Norbert Casteret, the newly invented screwtop bottle, Josephine Baker, the working class hero or the mutilé de guerre (who gets a set on the Metro along with civil servants on official business and pregnant women).

The five quotes are:
a- He who fights with monsters might take care lest he thereby become a monster.
b- The true man wants two things: danger and play. For that reason he wants woman, as the most dangerous plaything.
c- To live is to suffer, to survive is to find some meaning in the suffering.
d- You must have chaos within you to give birth to a dancing star
e- Faith: not wanting to know what is true.

I could go with 1d, 2a, 3c, 4b, 5e, or just write them on strips of paper and hand them out randomly at the game along with a corresponding drive.