A: 

Looks to me that the case is quite simple. You can use True Type fonts and use

Here's the example:True type fonts for PIL

Here you can find Hebrew True Type fonts: Hebrew true type fonts

Good luck or like we saying in Hebrew - Mazal' Tov.

Roman Kagan
Thanks for replying, but you haven't answer the question. As i wrote - I know how to write TTFs, and I already have TTF fonts.
Berry Tsakala
+1  A: 
ΤΖΩΤΖΙΟΥ
You didn't really answer, but you help seeing the bug:Only DejaVuSans.ttf and Lucidaxxx.ttf behave correctly under PIL!All the rest of my TTF files produced wrong output (but they behave nicely outside of PIL)You can try other fonts, e.g. Arial.ttf
Berry Tsakala
A TrueType font (or OpenType font) does not necessarily mean it's a complete and useful font in all applications. Michael Kaplan (working for MS currently and very related to Unicode issues) calls ArialUni an "MS Office font", not an "OS font", whatever he means by it, here: http://blogs.msdn.com/michkap/archive/2007/07/15/3890144.aspx
ΤΖΩΤΖΙΟΥ