Some really great choices here. 
Crazy People - always makes me belly laugh, especially the "hello" guy and his "hello song".
Some Like it Hot - what a script, what a cast.
That Touch of Mink - Cary Grant trying to get Doris Day into bed and all the mishaps that ensue - what's not to like?
Calamity Jane - fantastic songs and gags.
Crocodile Dundee - the sequel is just as good, too.
What About Bob - Bill Murray at his funniest.
Murder by Death - Maybe the title isn't so inviting, but the situations are brilliant!
Victor/Victoria - one of the classics, surely.
Flight of the Navigator - I've watched this so many times and it never gets old.
Galaxy Quest
Even a really bad day would seem brighter after one of those.
EDIT: There are just so many, I keep adding!

Crazy People - always makes me belly laugh, especially the "hello" guy and his "hello song".
Some Like it Hot - what a script, what a cast.
That Touch of Mink - Cary Grant trying to get Doris Day into bed and all the mishaps that ensue - what's not to like?
Calamity Jane - fantastic songs and gags.
Crocodile Dundee - the sequel is just as good, too.
What About Bob - Bill Murray at his funniest.
Murder by Death - Maybe the title isn't so inviting, but the situations are brilliant!
Victor/Victoria - one of the classics, surely.
Flight of the Navigator - I've watched this so many times and it never gets old.
Galaxy Quest
Even a really bad day would seem brighter after one of those.

EDIT: There are just so many, I keep adding!
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