I tend towards comedies:
What About Bob
What's New Pussycat
Analyze this (i don't like Billy Crystal but I adore Lisa Kudrow)

And for tv I loved Headcase and Web Therapy (lisa kudrow again) and Dr. Katz, Professional Therapist
And of course Ally McBeal

One of the best books I read was by Roberston Davies and in one book had the lawyer write arguments defending himself to the therapist
The other book is Other Women by Lisa Ather