I loved Caddyshack since I first saw it, have seen it dozens of times. This review is geared more toward the new Blu-ray edition. Previous DVD editions, inluding the 19th Anniversary edition, were disappointments as they looked like VHS with little improvement to the picture quality. I'm glad to say that the Blu-ray edition finally improves on the picture quality. Although not 100% perfect, it looked pretty damn good for the most part on my 55" Samsung TV. I think the lighting was inconsistent when the film was made so there was only so much they could do.
On the Blu-Ray release, they've added a 1-hour+ documentary on the making of the movie that gives a lot more insight/information than previous editons of the DVD. They interview more cast members (not the "stars" but more of the bit players) and you get a better feel for how the movie was originally setup to be something similar to Animal House where the caddies rebelled against the country club elite. The movie then slowly morphed into what was released as one-by-one they brought in the big talent. Bill Murray was brought in late and was only supposed to have one scene but he wound up stealing the show. Most of the "story" about the caddies was cut, IIRC they said they had about 4.5 hours of footage. The only down side of the documentary is there is a lot of repetition and you sometimes wonder if you've gone back to the start because you see thee same photos multiple times.
All-in-all I think the Blu-ray is a MUST HAVE just for the picture quality improvement over previous DVDs (which su-su-su-sucked). The documentary, although repetitive, is also nice to have.