On my computer I have only one file for Ubuntu Condensed font, it seems. Namely: /usr/share/fonts/truetype/ubuntu-font-family/Ubuntu-C.ttf However, in LibreOffice I can make this font bold and italic: On Ubuntu font tester web page I can also set different font weights (namely, regular and bold) and different font styles (namely, normal and italic) for the Ubuntu Condensed family. In CSS this might translate to: /* CSS for bold and italic Ubuntu Condensed font */ font-family: Ubuntu Condensed; font-style: italic; font-weight: 700; Or: /* CSS for regular and normal Ubuntu Condensed font */ font-family: Ubuntu Condensed; font-style: normal; font-weight: 400; However, when it comes to Python's PIL/Pillow, I couldn't find any working option in ImageFont that would modify the font's style and/or weight other than load different font files with ImageFont.truetype() function. For the "regular" Ubuntu font (not Condensed) I could load one of the four separate files to get normal, bold, italic and bold+italic styles in Python: /usr/share/fonts/truetype/ubuntu-font-family/Ubuntu-R.ttf /usr/share/fonts/truetype/ubuntu-font-family/Ubuntu-RI.ttf /usr/share/fonts/truetype/ubuntu-font-family/Ubuntu-B.ttf /usr/share/fonts/truetype/ubuntu-font-family/Ubuntu-BI.ttf But not for Ubuntu Condensed. So the question is, is it possible to draw an image with bold and/or italic Ubuntu Condensed font in PIL/Pillow? Or is it possible, at least, to generate four Ubuntu Condensed files, so that it can be used like the Ubuntu font from Python? Continue reading...