When Harry Met Sally...
A strong film that's strongest when the bracket is deepest. When Harry Met Sally... at 50% across 294 matchups is already above average — and the late-round numbers push it higher. The film that defined the modern romantic comedy and the standard every entry since has been measured against. On a ballot, it doesn't just represent itself — it represents the genre.
Synopsis
Sex always gets in the way of friendships between men and women. At least, that's what Harry Burns believes. So when Harry meets Sally Albright and a deep friendship blossoms between them, Harry's determined not to let his attraction to Sally destroy it. But when a night of weakness ends in a morning of panic, can the pair avoid succumbing to Harry's fears by remaining friends and admitting they just might be the perfect match for each other?
40%, 67%, 62%. When Harry Met Sally... doesn't just survive deep bracket runs — it improves through them, arriving at the final in better form than it started.
The Fall Guy is the nearest thing to a true rival at 53%. The margin is slim and the outcome still feels unsettled. When Harry Met Sally... owns A Few Good Men at 100% but Notting Hill flips the script entirely: just 17%.
When Harry Met Sally... owns Valentine's Day Showdown 2026. 10 Things I Hate About You is the usual final opponent, and at 79% it's not much of a contest.
#3 of 8 in Rob Reiner's filmography. The Princess Bride sets the pace at 65%, but When Harry Met Sally... is competitive with the top of the catalog.
#2 of 8 in Valentine's Day Showdown 2026.
Think it deserves the gold? Cast your vote now.
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