My Rating: 3.76/4 (aka A must-see high school classic)

One line summary: Two sisters navigate the fun of high school relationships.

The Deets: I am a little embarrassed to admit I hadn’t seen this one before. But I am excited to share that we watched it on a rooftop in Miami, so that was cool. So much to love here – early Julia Stiles and Joseph Gordon-Levitt, and then oh what could have been with the great Heath Ledger in the male lead (w magnetic charisma), a sharp & witty script, and a cameo by Allison Janney as a writerly guidance counselor. Within the canon of great high school flicks – John Hughes’ legendary work and “Say Anything” – this one slides in just under the best of those, though some may argue it belongs in their rarified air. And especially for a Shakespearean guy like me, I enjoy the flowing sonnets; and even though you know exactly where love will eventually blossom, that’s most of the fun of it anyway.

Perfect for: When you’re in the mood for a throwback, to a simpler time without cellphones, and if you actually want to relive the pain and suffering of high school.

Where to watch: You can get it on Amazon Prime, Apple TV, Hulu, and other services because we live in a streaming democracy.

Food pairing: Feeling some serious Chinese food vibes here, but I am certainly not going to dictate your order. But obviously fried rice.