On Silicon Valley Zach Woods plays a gentle, vest-wearing startup barnacle named Jared, whose dark past emerges in improvised quips. ("I know what it's like to only be able to rescue half your family.") Woods's career has had its own dark interludes, starting with his acting headshots. It was 2001, and he was a wide-eyed 16-year-old from Bucks County, Pennsylvania—a late bloomer reeling from his first kiss. When he arrived at the photographer's studio he balked at the walls, which were covered in erotic paintings. The photographer, Woods recalls in a haunted voice, went to great lengths to relax him: "She was like, 'You're tense! You're tense!' She took a parrot out of the cage and said, 'This is Faust, Faust will relax you.'" Even holding the comfort parrot, Woods remained tense, so the photographer pulled out the big guns: "She told me to say"—he's barely comfortable saying it now, and the word breaks as it comes out—“ ‘cuh-hunt.’ I was 16, and I had a bird on my shoulder, going, 'Cuh-hunt? Cuh-hunt?' while she took my picture. It was so uncomfortable."

Flash forward to Woods, age 33, on a windy hilltop not far from Los Angeles. GQ personnel surround him, stifling their laughter at his never-ending stream of jokes with varying degrees of success. He's holding an even bigger bird, a hawk, and photographer Carter Smith is firing away. The hawk is fussy. For long moments she perches regally on Woods's arm, but then she starts flailing, feathers and talons akimbo. "Watch out for the talons," the hawk's cheerful handler says helpfully. Woods begins talking soothingly to the hawk, almost in a whisper. The crew looks on nervously, nobody breathing. The hawk settles and stares deeply into Woods's eyes. Woods holds her gaze, then suddenly looks off into the distance. The hawk looks with him, and for a second they are the same in profile, chin and beak nobly tilted upward, two handsome avian faces surveying their domain.

(Zach On Water: “In bottled water, there’s a lot of toxins. In a stagnant creek, worst you’re going to get is giardia. They say pain is just weakness leaving the body, and I feel that way about giardia.”) Jacket, $2,785, by Moncler C / Pants, $749, by Norrona / Boots, $1,365, by Moncler (Zach On Flora: “It’s very important that you be able to identify poison ivy. The way you can tell is poison ivy has a matte finish, five prongs, and smells like weed.”) Jacket, $2,295, turtleneck, $1,350, shorts, $925, tights, $1,350, by Valentino / Sneakers, $220, by Adidas Originals by Alexander Wang / Hat, $11, by Rothco

The day before Woods finds himself in the black eyes of a hired hawk, I meet him for an interview at a hotel in Los Angeles. He's a few minutes late, so I see him unfold his very, very long limbs from his Camry and lope over to the valet in half the strides of a smaller man. In a few more steps he's through the doors, holding out his hand and grimacing slightly.

We do some small talk, and it is immediately apparent that while his appearance suggests extreme awkwardness, Woods is a master of chit-chat. Woods's humor doesn't steamroll the people around him. Talking to him is like scoring the smart kid as a lab partner: He's doing all the work, but you feel smarter by osmosis. He grabs hold of an ordinary thing that you say, then sculpts it into something funny in a way that makes you feel like you, too, are hilarious. I tell him that I wish I could be more assertive when I park, and he nods seriously. "One time I was in Studio City and I saw a high school student get out of a Porsche at a sushi restaurant, toss his keys to the valet, and go in to eat sushi," Woods says. "If I had been that kid then, what level of douchery would I have risen to by now? That guy was like a dickhead prodigy. Where does that leave you to go, if you're heading in that direction so young? You have to get into actual moral crimes by the middle of your adulthood. If I had started that way, I'd probably be an arms dealer to questionable regimes." The sushi teen makes several reappearances over the course of our interview, and each time I thrill over the fact that we share an inside joke. I'm supposed to be the one putting him at ease, but here he is, trying to make sure I have a fun time in our interview.