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The thread is a recurrence of several others, that have run for several years. It would be too easy, repetitive and predictable if we just picked out 3 'masterpieces' such as Godfather, Citizen Kane or Casablanca from each others collections.

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And as for having 'a good grasp of film making', who gives a feck?? We all get hung up at some stage in our collecting about buying and watching what you are led to believe are must sees, but the true pleasure of movie watching is being confident enough to enjoy a film, and not worrying what pipe smoking, sandal wearing leather patched elbowed 'experts' may say about it.

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Plus what must always be kept in mind, a collection you view is likely to be a whole families list of dvds, and many great memories are often linked to times when some dvds are viewed, and therefore nostalgia when talking about certain films is common.
{climbs down from soapbox}

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Well, I'll take a stab at bob9000's collection. 

Best: 
The Man Who Fell to Earth (absolutely amazing film)
The Nightmare Before Christmas (the perfect film this time of year, I never miss watching it in October)
Dirty Dancing (one of the best romantic films, ideal for a rainy afternoon)

(Ignoring the obvious choices of Lawrence & LotR, two of my top 5 of all time  )

Worst:
Dogma (I know lots of people who love this film, but I absolutely hated it)
The Spirit (It was really pretty to look at, but there was nothing else there...)
The Grinch Who Stole Christmas (Possibly tops my list of remakes that should never have been made)

Most Needed:
Seven Samurai (An absolutely amazing film, and the perfect entry to Kurosawa's work)
Bubblegum Crisis (you have Tokyo 2040, is there a reason you don't have the first series?)
Princess Mononoke (you obviously enjoy anime, but I didn't spot much Miyazaki...)

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At the request of Stephan and to help keep the thread going, I'll do his collection.

Best:
Goonies-I watch this every year on Halloween, one of my top 10, I'd say.
Sound of Music-Just watched this the other day and had forgotten what a nice, well put together musical this was (if a bit long).
The Hunt For Red October-love this one...good actors, good action.

Worst:
Billy Madison-Not a real fan of Adam Sandler.  Think I've only watched one or two of his movies and actually liked them
Chuck und Larry (Chuck and Larry)
Hostel-yeah, not a horror fan at all.

Needed:
Buffy the Vampire Slayer-the seasons (or the movie.)  You have the one episode, but the rest are just as good!
Drawn Together-tv show from Comedy Central.  I see you have South Park and a few other comedies of that sort (Scary Movie, Queer Duck).  Drawn Together is cruder and more abrasive than South Park, I don't even usually admit to liking it much less owning it, but man, I've never laughed as hard as I have for this show.  The last season isn't the best, but the first two were very good.
Finding Nemo/Bug's Life-couldn't pick between the two; they're both really good.  If you liked the other Pixar films (you have Toy Story and Wall-E, it looks like), you'll enjoy these!