Please, provide the answers to following questions :
What is your Raspberry OS ?
Does your OS able to start a User Interface (x11) ?
To answer a bit your question, you'll need a video application on raspberry pi that can be launch in a terminal. For instance you could use VLC that is really great and once you're SSH connected to your Pi use the following commande :
vlc -vvv my_file.mpg
Obviously your video file should be located on the raspberry pi otherwise it won't work this way.
More information about VLC command line here : http://www.videolan.org/doc/vlc-user-guide/en/ch04.html
EDIT : About subtitle, if your subtitle has the same name than the video file then VLC will automatically play the video and overlay the subtitle to it ;)