Not putting these in order, just in order of what springs to mind.
1) Airplane! - just loaded to the brim with silly, but clever, gags. Particularly love the Ethel Murman cameo.
2) The Big Lebowski - just...everything great about the Coens.
3) In Bruges - probably ticks every genre, really - but its quotability is probably only rivalled by...
4) Anchorman - don't need to explain.
5) Mean Girls - It's just something I grew up with. Equally quotable.
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