You can sometimes fix that by editing the files of the subtitles. The Plain with border style wasn't displayed correctly in these subtitles:
[V4+ Styles]
Format: Name, Fontname, Fontsize, PrimaryColour, SecondaryColour, OutlineColour, BackColour, Bold, Italic, Underline, StrikeOut, ScaleX, ScaleY, Spacing, Angle, BorderStyle, Outline, Shadow, Alignment, MarginL, MarginR, MarginV, Encoding
Style: Default,Trebuchet MS,40,&H00E6F4FC,&H000000FF,&H00000000,&H00000000,-1,0,0,0,100,100,0,0,1,1,1,2,10,10,10,1
Style: Plain with border,Arial,30,&H00000000,&H000000FF,&H00FFFFFF,&H00000000,0,0,0,0,100,100,0,0,1,2,0,5,10,10,10,1
It was fixed by changing the bold attribute from 0 to -1. You can also just delete the styles completely. See docs.aegisub.org/manual/ASS_Tags for a reference of the ASS syntax.
You can extract subtitles from mkv files with mkvextract:
brew install mtoolnix
mkvextract tracks test.mkv -c UTF-8 3:test.ass
Another common issue is that VLC shows characters that aren't included in the default subtitle font as rectangles. It can be fixed by just changing the default font. You can also change the text rendering module to CoreText font renderer, but it makes text too thin in my opinion.
MPlayerX substitutes characters from other fonts by default. It has that second issue with some subtitles, but some are shown correctly by default.