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That’s not the show’s fault, obviously, but even with Kennedy, it’s a silly moment.) Some of the humor seems dated here in 2014, and despite considerable honing from Season 1, the show feels like it’s still grasping to figure itself out.
And then there’s Dan Futterman’s guest-starring role as a “gay straight man,” a character that probably played as a wicked, perhaps even astute, identity-bending tweak back in 1999, but is now just offensive—to both gays and straights.
What’s Good: A transitional season that was truncated because of Parker’s real-life pregnancy, these eight episodes hum with a ruefulness that is probably largely owed to the fact that they were the first to be written and shot after September 11.
Best Episode: “Ex and the City” The finale moment when Carrie dramatically walks away from Big after sending him off to his young fiancé may be a on the nose, and may have launched a thousand mean jokes (look it up), but it remains one of the most indelible scenes of the whole series—sexy, poignant, and free-spirited, it’s what first solidifies this show as a classic.
Worst Episode: “Games People Play” This isn’t the one with the “gay straight man” (an otherwise good episode that has Miranda, foreshadowingly, contemplating fertility), but it’s got weak conceits, like a guy who will only sleep with Samantha if his sports team wins and Jon Bon Jovi as a ho-hum one-off for Carrie, who finds herself in post-Big therapy.
A decade later, those trends are largely gone, but there’s still the show—this great, thrilling, maddening, occasionally dumb show.
As a longtime fan of the show who hadn’t watched an episode in some time owing to exhaustion—I probably tore through the whole series at least twice in 20—I decided to re-watch the entire thing recently to see how it looks now that its of-the-moment modernness has given way to vintage charm.
Each character, but especially Miranda, is still smart enough to question this whole enterprise—one episode even has Miranda openly complaining that all they talk about is men.