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Top 5 “WTF?” moments in Scorcese’s “The Departed”

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"OMG WTF?": Damon's shock won't compare to your own as "The Departed" slams one "WTF?" moment after another over your head.

So I have this friend. (Every truly interesting story begins this way, right?) You may have heard of him; his story is the stuff of urban legend. Or it should be. At any rate, he’s the guy who let a copy of “The Departed” — that would be the 2007 Oscar winner for Best Picture, savvy readers — gather dust on his TV stand for, oh, about six months. Yes, it sat there, untouched, unappreciated, unwanted and unwatched for six months. I’d mention it periodically (re: “aren’t you ever going to watch that?”) and he’d make some noise about not being able to make “that kind of commitment” to sit down and watch it. (He fancies himself something of a comedian, this one.)

Then one day something crazy and momentous happened: He watched it. And watched it again … and again … and again. (I can’t hazard a guess at how many times he’s seen the various parts in various orders; however, I suspect the number would make me cringe with laughter.) So you might say he’s become something of a “Departed” connoisseur.

It’s not surprising that during a recent discussion of great gangster films (“GoodFellas”: hell yes; “Miller’s Crossing”: I say also yes) “The Departed” came up. Of course, you can’t discuss “The Departed” without saying the words “what the f!@#$!?” (in that order and with an infinite number of inflections) roughly 30 times. It’s a film littered with “WTF?” moments; I’d bet my next paycheck it has, minute for minute, more “WTF?” moments than any movie ever made (excluding “Syriana,” which makes less sense the more I watch it, and “The Usual Suspects”).

So behold the birth of the newest list: The Top 5 “WTF?” moments in “The Departed.” (Note: There are spoilers ahead, so if you haven’t seen the movie (a) I blow my nose at you and (b) Stop reading, get off your duff and buy — not rent — it.)

5) Baby daddy drama: A weary, lonely shrink (the divine Vera Farmiga). Her is-he-or-isn’t-he? impotent fiancee (Matt Damon). Her hardscrabble but kind-hearted patient (Leo DiCaprio). Oh, what a love triangle it is, and in the next-to-last scene in “The Departed” we viewers — heads still reeling from Number 1 on this countdown — discover the head doc is in a family way. That’s surprise enough, but better still is Scorcese’s absolute refusal to divulge the father-to-be’s identity. (Even if you think you know, you can’t prove it.) I do so love a director who pimp-slaps me around.

4) Sweet revenge (the final scene): The last five minutes of “The Departed” kick you in the face, throw you to the ground so you can pick up the teeth you lost and then lift your spirits with a blackly comic and satisfying ending where Matt Damon’s charmed life meets a dramatic end — but in a way you’d never, EVER expect and with an abundance of sarcasm and satire. Consider it the bittersweet cherry topper on this “WTF?” sundae.

3) A guy walks into a warehouse … and gets thrown off it: Talk about a twisted punchline to that old joke. Captain Queenan/Martin Sheen’s untimely demise is one of those blink-and-you’ll-miss-it shockers, something so totally and wholly unexpected that even the shrewdest viewer/critic can’t see it coming. Once the shock wears off (it takes at least 10 minutes), the full impact will have you whispering “WTF?” with the particular abject hopelessness of a duped moviegoer who knows no explanation is forthcoming.

2) Will the real FBI informant please stand up?: So we have a rat who’s pretending to be looking for a rat … and a rat who’s pretending not to be a rat while looking for his own rat. Confused? A careful viewing of Jack Nicholson’s role in the second half of “The Departed” will clear up the mystery. Get used to whiplash; you won’t be shaking your head in disbelief so much as whipping it around constantly “Exorcist”-style. My response? W. T. F?.

1) I get capped, you get capped, we all get capped: This one will make you want to pull the “emergency stop” button before the elevator parks at your floor. This blow-your-mindhole moment inaugurates — with a very literal bang — a slew of gangland-style executions that become more shocking as the brain matter coats the walls. You’ve never seen a death scene this shocking — NEVER; it bears repeating — and you won’t again. It will have you reeling for days; in fact, it might have you shrieking “WTFF?” (“what the effing f?” of course). Thus, it is deserves the honor of being christened the Number 1 “WTF?” moment in “The Departed.”