I have no idea why this movie never really appealed to me, outside its better-than-average soundtrack. (Fun trivia: the song in the boombox scene was originally supposed to be the Replacements' "Within Your Reach," which is used elsewhere in the movie.) Something about the whole Lloyd Dobler mystique bothers me, but I can't put my finger on why. In his book, Sex Drugs and Cocoa Puffs, Chuck Klosterman talked at length (and with uncomfortable amounts of gender essentialism) about the cult surrounding Say Anything's lead character and its effect on women of my generation desperately trying to find their own "Lloyd Dobler." I dunno. The "sensitive guy" trope is all too familiar to those of us who came of age in the 80s and 90s, and yet, Lloyd was a pretty nuanced character. (Or, quite possible, a male "manic pixie dream girl.") A few years ago, C.L. Minou for Tiger Beatdown wrote:
Say Anything proves to be most effective as a meditation on what it means to be a “good man.” Not to take anything away from the marvelous Ione Skye’s Diane Cort — wonder of wonders, a woman in a studio movie who is smart, without being unattractive, unpopular, or unpleasant — the movie is centered mostly on the various modes of contemporary masculinity. What makes Say Anything different from just about every movie about masculinity today (and to be fair, a large chunk of movies from the ’80s) is that it sides against the Path of Greatest Jerkiness.Should we be rewarding "non-jerkiness?" I mean, not being a jerk should be the default.
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