Welcome to Shady or Not Shady?, the brand new thing we just made up in which we take a look at a morally ambiguous character from pop cinema and decide once and for all whether they’re — well, you know.
In this edition of Shady or Not Shady?, we’ll be parsing the actions of Matt Dillon’s character Jeffrey Willis, from Garry Marshall’s 1984 summer classic The Flamingo Kid.
The Setup: Jeffrey is from a middle-class Brooklyn family, and his father is hell-bent on his going to college. But when a day playing gin as a not-so-welcome guest at an upscale beach resort turns into a summer job, first as a valet and then as a cabana boy, Jeffrey is influenced by a definitely shady new role model (Richard Crenna’s card-sharp car salesman Phil Brody) and begins to question his father’s insistence on hard work and planning over the easy road of bro networking.
The Evidence: Jeffrey gambles. He seems willing to bend the rules to get what he wants, regardless of whether what he wants is exactly morally right. He turns his back on his family in favor of shady, affluent new friends and a hot girl for whom he’s more-or-less just a summer fling. He covets an unearned higher status in life, and might betray his own best interests in order to attain it.
The Resolution: When it turns out that he’s just another lackey to Brody and that Carla isn’t going to suddenly decide to forego college for him, Jeffrey realizes he’s teetering on the edge of full-blown shadiness, and resolves to back away. He uses his gambling powers for good in besting the cheating Brody and winning back his and his friends’ money, and reconciles with his father and family.
The Verdict: While he was shown the degree of his slide into shadiness through no action of his own, he still made the decision to do the right thing when faced with the reality of his situation, not only for himself but for others. And for that reason, Matt Dillon’s Jeffrey Willis is... NOT SHADY.
Tune in next time!