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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. № 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. № 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. № 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. № 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. № 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. № 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. № 2

    Notting Hill (1999)

    Roger Michell

    Hugh Grant and Julia Roberts, with a hilarious supporting cast and a surprising amount of heart.

  3. № 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. № 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. № 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.