Top 5 Romantic Comedies
Only one movie made both of our lists, and it's not in the same spot.
Hear it on episode 7 at 47:37 →
Jeff's picks
№ 1
10 Things I Hate About You (1999)Gil Junger
Julia Stiles and Heath Ledger in a Taming of the Shrew retelling set in high school. One of the few movies Jeff actually rewatches.
№ 2
You've Got Mail (1998)Nora Ephron
Tom Hanks and Meg Ryan's Nora Ephron retelling of The Shop Around the Corner, which Jeff thinks beats the original.
№ 3
(500) Days of Summer (2009)Marc Webb
The Zooey Deschanel "dream girl" chemistry with Joseph Gordon-Levitt, told out of order, about the gap between the start of a relationship and real life.
№ 4
Crazy, Stupid, Love (2011)Glenn Ficarra, John Requa
Steve Carell's divorced dad gets a makeover from Ryan Gosling's ladies' man, with Emma Stone along for the ride. Fun, twisty, and funnier than Jeff remembered.
№ 5
She's All That (1999)Robert Iscove
A fun, nostalgic high-school transformation story from the early 2000s that still brings a smile. Jeff's a sucker for the secret-bet plot.
Matt's picks
№ 1
You've Got Mail (1998)Nora Ephron
Matt's number one and his very first movie date. Nora Ephron's writing holds up, even as the Instant Messenger of it all has become a time capsule.
№ 2
Notting Hill (1999)Roger Michell
Hugh Grant and Julia Roberts, with a hilarious supporting cast and a surprising amount of heart.
№ 3
Hitch (2005)Andy Tennant
Will Smith doing the charming persona he does best, with Kevin James and Allegra Cole as the hidden gem of the film.
№ 4
Runaway Bride (1999)Garry Marshall
Richard Gere and Julia Roberts in a sweet, PG, comedy-forward romance Matt has watched many times since seeing it in theaters in high school.
№ 5
To All the Boys I've Loved Before (2018)Susan Johnson
A Netflix teen rom-com Matt watched again this week. Hilarious dialogue throughout, with John Corbett in a supporting role.
You've Got Mail was the only film to land on both brothers' lists, Jeff at #2 and Matt at #1.








