A little back story. I have chronic tight calves. I roll them out consistently. In November I strained my Achilles. I was unable to stretch my calf out for 2 months. Since I have returned to running my it band has tightened up. I had problems with it last season and I found out my tight calf was the main cause of the it band issue. I have tried to loosen it but still no luck. I’ve stretched and rolled it, even used lacrosse ball. I can run about 25 minutes before the tightness turns to a tearing pain at the outside of the knee. Anyone have any suggestions on how to fix this? What worked last year didn’t help this year.
It’s almost certainly a biomechanical issue that can be fixed. I strongly recommend The Feldenkrais Method, as it worked for a chronic knee problem that bugged me for ages, and nearly prevented my running at all - I qualified for Boston a couple of years after that. You have to find the underlying cause, which may start in your shoulders, or anywhere.
BTW - I’m not a Feldenkrais instructor, and don’t benefit in anyway financially by encouraging it’s use. I just love to see people overcome what you need to overcome. Wishing you well with this pain in the butt! You can fix it!
Rolling to fix it being tight is good, but try to go back a step - What is the source of your tightness? If you fix the source, the rolling will maintain good muscle tissue.
I would look at your hamstring strength, hip abductor strength, and hip flexor flexibility. All three of those have had a bad impact on my ITB.
Look at the Thomas test for tightness of abductors? http://www.pthaven.com/page/show/157779-thomas-test Will tell you about hip flexor.
Look at this for butt muscle strength test? http://www.pthaven.com/page/show/157781-trendelenburg-sign-and-trendelenburg-lurch
A PT should be able to look at this stuff and find the root cause. I am not a PT, just a former patient 
Also VGA is good to watch you run on camera. Could be a form or shoe issue.
My glutes and abductors feel tight but they don’t seem to losen up with stretching or a lacrosse ball.
For stretching - this is my favorite stretch → http://www.youtube.com/watch?v=3svl4ifS9gc . Have to squeeze your cheekies while you do it, or it will stretch the wrong muscles.
Also look to weakness not just flexibility. Some muscles should be trained outside of running, I have had HUGE success adding a few weights to my diet. YMMV but I went from always injured man to train as much as I have time for man after some time in the gym.