Kiss Kiss Bang Bang

"Kiss Kiss Bang Bang" and the later "Iron Man" see Downey exhibit an equal amount of smarminess, but while the latter is nigh-unwatchable due to a variety of failings, writer and director Shane Black knows how to frame and contain Downey so that it works to his project's advantage, having him land every barb he throws while also keeping him likeable and neck-deep in a strange plot he's hesitant to shoot his way out of. It's one piece to the puzzle that is one of the best action-comedies of the Aughts, one that deserves far more love than it enjoys.

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