Remembered as the film in which Ben Affleck is so irresistible that he turns a lesbian straight (and hailing from a time period in which distributor Harvey Weinstein was behaving like a rabid animal in hotels all over the world), Chasing Amy is probably best understood now as writer-director Kevin Smith trying to make sense of why a beautiful woman with much more life experience than him might then find his comparative naivety appealing. Joey Lauren Adams is the subject both in front and behind the camera: the actress luminous onscreen as Alyssa and, presumably, at least a little bit bewildered offscreen as the real-life girlfriend who had prompted Smith to so fully excavate his personal inadequacies. Of course, a handsome actor on the verge of superstardom being cast as Smith's avatar likely took a little of the sting out of this public splaying. If nothing else Affleck, who incidentally sounds uncannily like Smith when the pair share audio commentary tracks, is able to wring an endearing lovesickness out of his writer-director's overwritten dialogue. Affleck's performance here flatters Smith and the writer-director knows it.
Similarly, in terms of aspirational tweaking, it's difficult not to wonder now if the framing of Alyssa as being much more fluid in her affections than the popular memory suggests is actually a misguided attempt at chivalry? If the character had instead only slept with a great many men, would Smith then be expecting his viewers (particularly a mainstream American audience back in 1997) to value her perspective even less? To side with the jealous and venomously bigoted Banky, as played by Jason Lee? Perhaps such a move might even generate disquiet for Adams the actress, since Smith was never shy about sharing his film's autobiographical underpinning? Gayness in this specific context, and this is discussed within the piece itself, is exciting rather than intimidating for Holden, Alyssa's prospective partner. He, foolheartedly, believes that his maleness confers on him some heteronormative advantage that the world's women lack. Sexuality then, especially in terms of promiscuity, is a recurring hang-up in Smith's work. An earlier embodiment of the writer-director, Brian O'Halloran's Dante Hicks from Clerks, blanched at the idea that his current girlfriend had been intimate with dozens of men before he entered the picture. Chasing Amy then reworks this comical overreaction, perhaps attempting to reassure Smith's now growing audience that, actually and under very specific circumstances, it doesn't matter to him if a potential life partner has slept with more people than he has.

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