Will: “The sad thing about a guy like you is in 50 years you’re gonna start doin’ some thinkin’ on your own and you’re gonna come up with the fact that there are two certainties in life. One: don’t do that. And two: You dropped a hundred and fifty grand on a f—-n’ education you coulda’ got for a dollar fifty in late charges at the public library.”
Clark: “Yeah, but I will have a degree. And you’ll be serving my kids fries at a drive-through on our way to a skiing trip.”
Will: “Yeah, maybe. Yeah, but at least I won’t be unoriginal. By the way if you have a problem with that, I mean, we could just step outside and we could figure it out.”
Later that night, after Will gets the phone number of Skylar (Minnie Driver), the woman Clark was trying to impress, his “How ya like them apples?” allows him to further embarrass the Harvard student and assert his own worthiness and his place alongside Chuckie, Bill, and Morgan. Weeks after, when Will bails on a job interview set up by Lambeau, Chuckie—in an amusingly tiny suit and his hair slicked back, a purposefully mocking mimicry of the moneyed—goes in his stead, swindling a “retainer” out of the interviewers. And when Will decides to finally tolerate one of Lambeau’s meetings, it’s with the NSA, a scene in which Van Sant relies on a smash cut to provide impact to Will’s criticism of the government agency. Filmed in one uninterrupted take, Will’s tirade gives voice to a deep distrust and resentment of American institutions, fueled by Will’s sense of himself as a member of the left-behind working class. “Why shouldn’t I work for the N.S.A.? That’s a tough one, but I’ll take a shot,” Will starts, before delivering an increasingly pointed answer about U.S. interference in the Middle East and North Africa, the overuse of military force, the volatility of oil prices, the corruption of private industry, and the complacency of the federal government.
“So what did I think? I’m holdin’ out for somethin’ better. I figure f**k it, while I’m at it why not just shoot my buddy, take his job, give it to his sworn enemy, hike up gas prices, bomb a village, club a baby seal, hit the hash pipe and join the National Guard? I could be elected president.”
“Situations get f**ked up and turned around sooner or later
And I could be another fool or an exception to the rule
They want you or they don’t
—“Say Yes,” Elliott Smith
The first person to call Will on any of this—to question how he wields his knowledge as a weapon, and hides behind the work of others rather than taking a chance on himself—is the court-mandated psychologist Will starts seeing in tandem with his meetings with Lambeau. After rejecting a slew of therapists from Lambeau’s world, mocking their work, and questioning their sexuality, Will acquiesces to meetings with Professor Sean Maguire (Williams), who teaches at a local community college, wears a well-loved Boston Red Sox bomber jacket, and was Lambeau’s freshman-year roommate at MIT.