Cannot watch iTunes purchased media with old Apple ID When attempting to watch purchased older material on iTunes I have been receiving a prompt stating that my MacBook is not authorized to view material. As the material was purchased unsing my original Apple ID - having since changed ID's twice - I am not able to view this material without entering the password for the old ID. I am then directed through iForgot to the change the password. Here iForgot states the prompting information provided is not recognized. As I cannot enter a password for this old ID I cannot view this material

I am having similar problems with apps purchased on my iPhone under this original ID. 

Sounds like others are dealing with the same issue. Any solutions?
If you remember the old id and still have access to the email account associated with it, you can definitely reset the password and then authorize your macbook to play these files.

iForgot will prompt you for information, but it should allow a password reset via email, not just questions. If you still cannot remember/access the info, I recommend sending apple an email via their iTunes store support and see if they can identify you via other means.

http://www.apple.com/support/itunes/contact.html