Family friendly movies we (my 14 year old daughter & I) have watched over the years and recommend:
-What’s Up Doc (hilarious, even with Streisand and O’Neal
-Return of the Pink Panther
-A Night at the Opera
-A Little Princess and The Secret Garden - the beautiful theatrical versions that came out, what, about 10 years ago (no time now to check IMDB). They are wonderful films.
We love it, too. Not a big Michael Caine fan, but I love that movie!
Hubby would never consent to rent a movie with John Candy and Steve Martin!
Too much of a good thing, eh? 
This one might surprise him. It’s not terribly subtle, but it’s more low-key than you’d expect. They both play it pretty straight, and it’s still hilarious in spots and touching in others.
Except for the scene where Steve Martin complains to rent-a-car lady.
Seriously Mad Hot Ballroom
How about the original version of “Yours, Mine, and Ours”? A family film, a semi-Christmas movie, funny and appropriate for all ages. My nieces and nephews all love it, from the youngest to the oldest. If you don’t know about it, it’s the true story of a mother with 8 kids who marries a father with 10. Lucille Ball plays the mom and Henry Fonda plays the dad.
StG
The Polar Express
StGermaine, the original Yours, Mine and Ours might be a good bet. I remember seeing bits and pieces of it when I was a kid, but don’t know that I’ve ever seen the whole thing. And it would please the middle daughter much more than the new one would, as she wishes Hillary Duff would just curl up and die somewhere; or at least shut up.
GuanoLad, the youngest one has already seen Polar Express (which isn’t necessarily a bad thing; you know at that age, they like to watch things over and over again). Do you think it’s entertaining enough for the older ones amongst us?
The first “Spy Kids” movie is a lot of fun. The second one is pretty good, too, and it has Ricardo Montalban and Holland Taylor!
We saw the first Spy Kids as a family (well, before we had our youngest, of course), and it was a lot of fun. Haven’t seen the second one yet. I’ll have to put that on the list of considerations.
I’d definitely say Elf. Silly, but funny and cute. My wife and kids were in hysterics. Lots of physical humor.
While I really, really loved Whale Rider, I’d say that it will either be lost on or distrubing to the little one.
Toturo is great. But my daughter’s favorite is The Cat Returns. Kiki’s Delivery Service is also very good and features voice work by Phil Hartman, which always makes me wistful.
The Wallace & Gromit shorts would be excellent for the first film. A tip: stock up on cheese and crackers beforehand. 
As for the second flick, I dunno if the five-year-old would really get into it, but Miracle (about the 1980 USA Olympic hockey team) is a lot of fun and would be particularly good to see sometime before the Torino Games in February. It’s probably O.K. for your youngest to see; the harshest language in it is a locker-room scene when Coach Brooks calls Rob McClanahan a “candy-ass”. There’s also some intense hockey action.
Either Monty Python’s **The Life of Brian ** or Mel Brooks’ The History of the World, Part I would be a funny third flick.
When your oldest daughter is a few years older, she may really appreciate the Thanksgiving comedy Home for the Holidays, as I have.
I would agree, but hubby does not like Monty Python or Mel Brooks! (Yeah, I know, I know). The other suggestions sound good.
Tuck Everlasting, a totally unique story.
Funny Farm, I laugh every time at every joke.
The Rocketeer is a wonderful movie, full of action and color, and suitable for family viewing.
Of course, I may be prejudiced.
I liked it. It’s good enough for older people to enjoy the story, though it may not go down in history as a classic. And it’s quite a thrill ride.
March of the Penguins - I was stunned by how good it was.
We rented this over the weekend; for my money, just the fact that it was narrated by Morgan Freeman was enough to make me want to see it.
I’ll put The Rocketeer down as a possibility, too.
Is that the one with Jennifer Connelly naked in it?
I’ll suggest Christmas Vacation with the one caveat about the Chevy Chase, “Just blousing…browsing” scene. I think it would go right over the head of the 5 year old who will then laugh at Chase’s physical comedy. The original rating was PG 13. It is still a very funny movie.
“Shitter’s full!”