With grizzled scruff and a conservatively amused smile perpetually plastered on his wrinkled, half-flabby face, the title character of Bette Gordon's Handsome Harry is something one doesn't often see in film, independent or otherwise: a genuinely interesting middle-aged protagonist. The character's soft piquancy resides in the manner that screenwriter Nicholas T. Proferes has managed to sidestep but politely nod toward tired age-isms. Harry (Jamey Sheridan) isn't a has-been or an almost-was who strayed from the chosen path (he seems to have been a mechanic since the end of his military service); his regret, while palpable, resists the aroma of a cautionary tale, particularly where filial estrangement is concerned (his awkward relationship with his twentysomething son appears to be no one's fault); and while he harbors Hollywood's standard Big Dark Secret beneath his aloof friendliness, he's sublimated his intense guilt into a somewhat gratifying, if far from ideal, small-town divorcée's niche. Unlike Otis "Bad" Blake or Randy "The Ram," Harry's not a broken shell of a man living in the shadow of an ebullient youth; he's simply carriaged with vintage perfidy, the abrasive specifics of which are gradually unspooled throughout the film's plotline.
Harry is, furthermore, charming (in an old-fashioned, whiskers-and-whiskey sort of way), so much so that when a bartender with eyes for him offers a blowjob he can only stare, chivalrously taken aback. He doesn't seem at all like the sort of man who would venture out of his comfort zone to confront navy buddies he hasn't seen in years about the events of one blisteringly abusive night in a spontaneous attempt to stitch together a more precise tapestry of blame—not even after having watched one of those fellow veterans, Kelley (a phoned-in Steve Buscemi), beg for deathbed absolution. The road-trip-to-the-past premise is creatively structured as a journey of self-discovery, naturally; Harry starts off with the intention of somehow fulfilling an unspoken promise to Kelley before it becomes clear that his own hand in the ultra-violent hazing was far filthier.
But therein lies the primary handicap of Handsome Harry: Gordon and Proferes detail their protagonist with authentically complex fleshtones, but splash on each new revealing coat with a jarring lack of finesse. The non-confrontational Harry taciturnly intervenes when he discovers one of his fellow sailors (John Savage) has metamorphosed into a red-faced, impotent wife-beater, but by the time he catches up with naval soldier-turned-professor Porter (Aidan Quinn), he's bluntly calling him out on his hypocritical pacifism before a throng of revering students.
The movie has other blemishes, to be sure. The dialogue tends to merely graze the characters' feelings, lapsing into trite confessionals and confounding attempts at hip speak (has any jazz fan ever referred to Oscar Peterson as "Oscar P"?), and grating but narrative-necessary flashbacks pepper Harry's thoughts with stereotypical strobe-and-sepia displays of loud, juvenile sensationalism. The film also has a quiet, muted color scheme of flat grays and glistening browns that impressively underscore Harry's dullness at the start and then neglect to develop along with his resurgence of emotion. But despite being built around a tragic epiphany of self-knowledge (an epiphany that, in and of itself, is rendered both sensitively and believably, despite the potential for musty liberal claptrap), the movie seems only perfunctorily interested in its main character's growth. Like its likeable if unevenly cultivated protagonist, Handsome Harry knows what and who it wants to be—it just takes the most self-defeating and inorganic path possible to get there.