I've had lots of about bad shoes and its hard to say what is worst. Here are some that come to mind:
Adidas Oregon - way stiff and way uncomforable
Adidas Cubato+ - made my knees hurt first run out
Asics GT-2030 (or 2020?) - felt like the front of the shoe was separate from the rear and they were breaking my feet in half
Nike Zoom Trail S - large 3+" holes in uppers after 10 runs
Nike Pegasus/Pegasus Plus from the '80s
Nike Run Avant - instant achilles pain
On the other hand, I like some of the shoes/brands mentioned already, like Puma (2 pairs of Trailfox 4, one retired at 1,750+ miles and the other 1,300+ miles and going), Adidas (Adios 2, Rocket), Nike Frees (some of the models that lasted a long time anyway), and Altra (Superior... incredible to have a shoe shaped like my feet and not pinch my pinky toes which have been deformed/turned sideways due to never having enough room in my shoes).