I've found that as I have matured as a man crying is no longer something I can do (yet). I have had a tear come out once in a while depending on the situation but I haven't had a good racking sob since I was 14 or so.
But... I wish I could. There have been times in my life where letting go would feel good. Letting all that emotion, be it anger, frustration or sorrow sit in my chest and mind for days sometimes leaves me feeling like it causes lasting damage to my soul if it happens in frequency.