I love a good romantic comedy but most of them aren't very good. I'm no expert but to me this is how the genre family tree looks. Hop on the 400 year romantic comedy train.
  1. Much Ado About Nothing ~ 1598
    This play is ostensibly a retelling of a classic story of love and deception, but the Beatrice/Benedict "subplot" is, as far as we know, Shakespeare's invention. And really it is the main plot: the one we are most invested in, the one into which Shakespeare puts his theatrical genius, and perhaps the original modern romantic comedy. Consider the Kenneth Branagh film for a wonderful classic take, or Joss Whedon's delightful modernization. Or even better: Both.
  2. Pride and Prejudice ~ 1813
    Ignore for a moment that this is the story of marrying off your daughters to rich men and let the incredible wit and charm sink in. With its strong independent female lead this story is surprisingly modern; so much so that you can't help but think it influenced every rom com that came after. It's a time commitment but consider the BBC/A&E 6 hour miniseries version which is beautifully produced and a perfectly acted by Jennifer Ehle as Elizabeth and Colin Firth as Darcy.
  3. Bringing up Baby ~ 1938
    This is a slapstick take on the form and a little insufferable for it. But it's an early Hollywood take on the genre with big stars and all the fundamentals of the romantic comedy.
  4. Breakfast at Tiffany's ~ 1961
    In this twist on the form the block our lovers face is endogenous. She's broken and so is he and I suppose neither believes they deserve the love they want. It's a powerful take on the trope fueled by Capote's literary genius (although the novella it's based on is not technically a romcom since in that version the lovers don't make it.)
  5. When Harry Met Sally ~ 1989
    The romcom was out of fashion for a long time before this brilliant film resurrected it with more modern themes. To me this is the very best modern romantic comedy and it holds up amazingly well for a 30 year old film. It's also reconnects to the past, more closely hewing to the Much Ado/Pride and Prejudice model than earlier films. If you've never seen it do yourself a favor and watch it this weekend.
  6. Eternal Sunshine of the Spotless Mind ~ 2004
    After the incredible success of Harry and Sally romcoms became sure fire studio wins and that brought a typical derivative Hollywood race to the bottom in terms of quality and story. This was one of the first films I think really brought something fresh with its sci-fi undertones and inspired subversion of the standard form. It's a classic romcom in the fundamentals but structurally entirely unique. It helps that it is also beautifully acted by Jim Carey and Kate Winslet.
  7. Castaway on the Moon ~ 2009
    The Korean film industry brings us this thoroughly original take where our lost and lonely lovers are frustrated in their cute-meet by their total isolation from the world and (almost) from each other. It is fresh, funny, touching, and relevant.
  8. Silver Linings Playbook ~ 2012
    Silver Linings Playbook did for the 2010s what Harry and Sally did for the 80s, making the standard cute-meet setup thoroughly relevant to a mixed up conflicted and fundamentally lost generation unsure anymore what it even means to be sane.