Grosse Point Blank(1997)
John Cusack's turn as repentant hit man Martin Blank marks the single greatest '80s throwback, killer-for-hire rom-com ever made. You know the story: boy meets girl, boy stands up girl on prom night, girl's heart is broken, boy becomes professional killer. It's an age-old tale and, thanks to Cusack's charming killer and a fresh-faced appearance from Minnie Driver, manages to be both charmingly romantic (he literally kills for her) and darkly comic. This remains the only film from screenwriter Tom Jankiewicz and a delightfully different romcom that stands head and shoulders above its peers - and boasts a more impressive bodycount to boot.
Being John Malkovich(1999)
This film makes the list for one simple reason: it proved, once and for all, that a film doesn't have to make any sense to be great. Impossible to sum up in any thirty-second studio pitch -low ceilings, puppets, and a sinister conspiracy focusing on John Malkovich's brain and the New Jersey turnpike are all involved. But what's great is that Charlie Kaufman's insane script, Spike Jonze's delirious direction and a cast of A-listers playing wackily against type somehow add up to one of the cleverest, silliest and utterly weirdest films you'll ever see.