Wait Until Dark (1967)

With as much suspense as you can stand, a young woman learning to cope with her recent blindness is terrorized by henchmen of a crazed killer desperate to find smuggled heroin that was given to her husband at the airport. The very limitation that makes her vulnerable provides an unmatched skill she’ll need to survive after letting the thugs into her home, believing they’re old friends of her husband’s.

Catch-22 (1970)

War is absurd in many ways, especially the unique subculture that forms in isolation. The very qualities that make this depiction stand alone keep it from being a favorite. Though adaptations of the novel abound– it’s easy to see why an Air Force pilot would be desperate for a diagnosis of “crazy” so he can get out of future missions– never has such a notable cast been assembled.

And unlike like modern stories that mostly highlight the seeming thrill of combat, this film’s non-linear structure gives a surreal quality to an ordinary routine, in which trauma blends with even the most mundane tasks, such as clerical duties and laundry. Unlike depictions of war that debuted around the same time (e.g. MASH), rather than merely utilize sarcasm, its unflinching dry humor highlights the same dark comedy found in the desperation, resourcefulness, futility (and, of course, the irony) of hollow victories.

Grosse Pointe Blank (1997)

I’m Martin Blank. Do you remember me? I’m not married, don’t have any kids and I’ll blow your head off if someone paid me enough.

So John Cusack wears a trench coat about as often as Julia Roberts expels a hearty chuckle and Tom Cruise runs. What of it? Yes, it features multiple Cusack family members and friends. So what? Everyone’s either trying to squeeze some deeper meaning out of it or point blank doesn’t get it. Yeah? Get what? Get back. I haven’t come across such swift witty dialogue since The Big Sleep.

Here’s the sitch: a profession hit man has a job to do back in his home town of Grosse Pointe, which happens to coincide with his ten year high school reunion. While in town he crosses paths with the ex-girlfriend he stood up on prom night to join the army (before he dropped out and went into business for himself), a rival hired to eliminate him and an old frenemy with a ‘join or die’ proposition, all with two government agents on his tail.

They all have husbands and wives and children and houses and dogs and, you know, they’ve all made themselves a part of something and they can talk about what they do. What am I gonna say? ‘I killed the president of Paraguay with a fork. How’ve you been?’

City Island (2009)

Loyalty is tricky; eventually, everyone must choose between the bonds of family and their commitment to guarded secrets, whether fledgling, dark, or just plain odd. Though everyone wants to preserve their image, they need someone to come and pull the threads that are already unraveling. And sometimes that person, who has the most for which they should feel ashamed, turns out to be the only one who understands the freedom of truth.

So I Married an Axe Murderer (1993)

With a title that’s a dead giveaway—or is it??—the initial charm of this quirky dark comedy is in its spirited characters; the enduring appeal is in the chemistry between them. Bursting at the seams with talent, cameos and quotable lines, particularly as the lead actor also plays a caricature of his real-life Scottish (i.e. loud, tactless, accordion-playing, Rod Stewart-idolizing) father.