Baby Geniuses 2. Hands down.
'War Stories'
Buffista Movies 5: Development Hell
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The Whole Ten Yards is definitely in the running. The first movie was surprisingly okay, but not great. Certainly not enough to warrant a sequel.
I think the last Christopher Reeves Superman movie (with the environmental theme?) is a contender.
Also Stuart Little 2
Godfather 3
Jaws 3 in 3-D
Garfield 2
Stayin' Alive
Grease II
Three Men and a Little Lady
Kids' movies (or movies with kids) do seem to be among the worst offenders. I'm going to have to disqualify "Stuart Little 2", though, because anything that gives Hugh Laurie a paycheck is okay in my book.
Jurassic Park II
Anything Animated Disney II (Cinderella II, Brother Bear II [was the first one even good????], Lilo & Stitch II, the abominable list goes on....)
I think the last Christopher Reeves Superman movie (with the environmental theme?) is a contender.
Superman IV: The Quest for Peace. With Jon Cryer as Luthor's nephew for youth draw (oy!).
Godfather 3
Poor Sofia - the meta of her getting shot at the end of the movie and exclaiming "Dad!" is hysterical.
I'd like to submit Speed 2: Cruise Control. If a subtitle was EVER a warning...
Depends on your meaning of pointless. A lot of these came after unexpectedly profitable originals.
Ocean's Twelve?
Choose your own meaning. I'm not very picky.
I'd mention Highlander 2: The Quickening if such a movie ever existed, but since it didn't, I won't.