If The Heartbreak Kid brilliantly anticipated all manner of awkward cringe-y comedy to come, this takes an even odder, altogether more stylized approach that feels almost as proto-Wes Anderson as like-minded oddball early '70s comedies like Harold and Maude or Brewster McCloud, except you know, much darker and stranger. Not unlike a '30s screwball comedy seemingly cryogenically frozen and unthawed amidst post-'60s disillusionment. So, like Bringing Up Baby dipped in battery acid, basically.
A more challenging romantic comedy than usual, as not only are the characters goofy, but none of them are at all likable. Matthau's acting is audacious; he's not an endearing rascal, but a despicable duplicitous gold-digger of an anti-hero. Director May portrays gazillionairess botanist Henrietta with edgy dorkiness. You don't really root for anyone, but you find yourself riveted with bemusement.
Awkward, uncomfortable and misanthropic, but also hilarious. Matthau really strikes the perfect, and precarious, balance between being despicable enough that you want to root against him, but sympathetic enough that you secretly hope he succeeds. It helps that the entire film is populated by despicable and selfish people, so one is free to delight in schadenfreude without reservations. May's character is the counter to all of this, despite her own massive failings, and sets up some great comedy.
It's not usually the case that something so atrociously filmed has such outstanding support in leads. I was at odds with myself through its entirety to how I should rate this.
Practically on the same level of genre revisionism as McCabe & Mrs. Miller. It'd definitely be on that level if it were presented in its original form. It's dark and cynical, but also really funny and totally heartwarming in the end. Matthau and May are brilliant and great together.