Zach Woods, Hollywood’s Favorite Awkward Tall Boy, Should Maybe Be Its Spiritual Guru Instead

Zach Woods can trace his entire career back to his childhood braces.

The Silicon Valley alum, who is currently starring on the HBO comedy series Avenue 5 and can be seen this weekend opposite Will Ferrell and Julia Louis-Dreyfus in the movie Downhill, was a trumpet kid. He desperately wanted to be a jazz musician. But on top of the other seismic traumas that metal orthodontia can inflict on a pubescent male’s life, the studs and wiring have a catastrophic consequence on a budding brass man’s embouchure, effectively disabling him from tooting out anything pleasant from his horn. 

So the Pennsylvania-raised teen turned to comedy.

A career performing for laughs wasn’t exactly written in the stars for the 35-year-old actor. In fact, he bombed his very first joke. He was 5 years old at a cousin’s birthday party. Everyone had to go around the room introducing themselves: “I’m Joe...” “I’m Megan...” When it came to Woods’ turn, he said, “I’m hungry.” A classic dad joke delivered in deadpan by a kindergartener. Among his tottering peers, it went over like a lead balloon.

His father says that he always suspected his middle son was going to be funny one day, because he was always so incredibly not funny growing up. “He was like, ‘You would make horrible jokes all the time,’” Woods remembers. “And then he realized, ‘Oh, he’s practicing.’ Like, if he’s failing with this much frequency at being funny now, eventually statistics point to him being actually funny at some point.” 

Woods is reminiscing from the top of the world. Or, at least, the top of Park City, Utah. 

He’s there for the world premiere of Downhill, a remake of the Swedish black comedy Force Majeure, at the Sundance Film Festival. Don’t let the reputations of the cast fool you. Louis-Dreyfus, Ferrell, and Woods, who aside from Silicon Valley is best known for his run on The Office and scene-stealing turns in movies like Spy, aren’t uniting for a raucous comedy. The laughter here comes from existential unease. 

When an avalanche barrels towards a family of vacationers who are eating lunch while on a European ski trip, the father (Ferrell) grabs his phone and runs for safety rather than protect his wife and sons. When all emerge unscathed, a married couple is left questioning their relationship, and an innocent coworker (Woods) there just to have fun with his new girlfriend is propped up as a foil for an embarrassed father’s crisis of masculinity. 

Over a Virgin Mary and coffee at the restaurant in the uber-luxe Stein Eriksen Lodge, where wealth seems to waft through the air in concert with the steam from après-ski hot toddies, Woods apologizes for a bout of deliriousness, owed partly to lack of oxygen and partly to the lunacy of promoting a film at Sundance.

“It's like the ‘Try to Stay in Your Own Skin’ Olympics,” he says. “You’re in all these situations that are almost designed to divorce you from your own personality, where someone's trying to give you, like, a pair of women’s boots, and someone’s taking a picture. And then there’s Pizza Hut...” a reference to the peculiar, relatively new addition to the pearl strand of branded “lounges” like Acura, Chase Sapphire, and WarnerMedia that dot Main Street in Park City. “It’s just like this maelstrom of promotional and media stimuli.” 

Keeping a stronghold on his personality is a running theme of our conversation. Arriving at a personal understanding of who he is has been a complicated journey, as one could reasonably expect for a 6’4” comedic actor who spent the first decade of his career cast in roles defined by a certain kind of physical awkwardness. 

Around 2010, for example, just before being cast on The Office as Gabe, a skittish corporate mouthpiece, he started to gain notoriety for his YouTube series, “The Most Awkward Boy in the World,” in which he plays a lanky college-aged boy with glasses stunned into nervous panic by various social interactions. The character, usually in an ill-fitting Oxford shirt sloppily tucked into khaki pants, looks like the kind of lanky boy who will probably age into a distinguished, handsome man, which Woods certainly has. 

It’s tempting to label Woods as self-deprecating, though he is probably closer on the spectrum to self-awareness. He is gracious, nearly excessively so, expressing thanks not just for interesting questions but even the mere opportunity to think about the things he’s being asked about. It’s a fascinating blend of kindness and assuredness, combined with a realization that not everyone in the world shares that quality—though he wishes they did, for their sakes above all of us.

He remembers having to take ski lessons for Downhill because, well, he didn’t know how to ski. There were ski doubles for action shots, but he had to be able to navigate competently for dialogue scenes delivered while standing in the snow. The lessons were hard, and they were terrifying. 

“They kept yelling, ‘Pizza! Pizza!’”—the trick where new skiers pivot their skis into a triangle in order to slow down or stop—“as I watched these beautiful Aryan children, like the 4-year-olds, practice jumps next to me.” No matter how many times “pizza” was shouted, he couldn’t do it. He could not stop. “I was quietly protesting to the ski instructor that I couldn’t do this, and then I’d look over and little Sven, or whatever, would have already mastered a 360 and is back drinking hot chocolate.” 

He’s laughing now, but the whole incident sowed the seeds of something bigger and more meaningful he’d been thinking about for a while.

“Maybe this is all in my head, but I feel like people think that, because you’re a guy, you’ll be prickly if they talk down to you or take care of you,” he says. “But all I want from them is to take care of me like a newborn babe. Don’t put too much faith in me.” 

The word faith turns out to be an interesting springboard. 

Woods attended New York University, essentially as a means for continuing improv classes at the Upright Citizens Brigade that he began taking at age 16, after having to give up the trumpet. He was in the university’s Gallatin School of Individualized Study, in which students can curate their own courses and develop their own major. Woods declared his to be The Intersection Between Christianity and the Civil Rights and Abolitionist Movements.

After a bit of a stunned silence after learning this—it seemed to come from left field for a white boy from Pennsylvania pursuing a career in comedy—it began to make sense. 

Woods has a way of thinking about the world that is constantly surprising throughout our conversation. It’s a perspective that colors how he looks at everything: acting, growing up, dating, his tallness, this interview, children’s movies, being propositioned by prostitutes in Budapest, meeting celebrities, faith, masculinity, or even a Sundance Film Festival lounge where celebrities take their photos with Pizza Hut.

He’s an Awkward Tall Boy who became a Comedy It Boy, and who is now coming to terms with becoming a man, both on-screen and off. 

“I had this Benjamin Button version of social competence where when I was in middle school, I was the most confident I’ve ever been. I felt very cocksure and socially adept,” he says. Heck, he was even voted homecoming king. “I didn’t experience myself as an awkward person until adulthood.” Now, you could say, kicks off phase three. 

There was something stealthily renegade about the roles Zach Woods has played while riding his “breakout star” wave over the last 10 years. 

Gabe on The Office may have been jittery and lacked social graces, but he was sweet and driven and knew his moral boundaries. It’s probably playing Jared on Silicon Valley that elevated him to a new level of recognition. On the Emmy-nominated HBO series, which finished its six-season run two months ago, Jared bumbled through the tech industry with a puppy-dog eagerness to please, often at his own tragic expense. 

These are characters that bucked against what had been a mainstay of comedy the decade prior, boorish laughs soaked in a certain bro-ish machismo. He was playing male characters that weren’t assholes, yet they were still as amusing as the Apatowian-adjacent creations they shared the screen with. The revelation: You could be funny without being a dick.

We bring this up to Woods, and he’s appreciative. What we didn’t expect is that it would inspire a veritable sermon about why he got into acting, the ways in which TV and film can change the world, and The Velveteen Rabbit—as in the 1922 children’s book by Margery Williams. Not a word of it was off-topic. It was even strangely moving.

Specifically, he brings up the passage in which the Rabbit asks the Skin Horse, “What is real?” The Skin Horse replies that “real” is something that happens to you when a child plays with you for a long time. The Rabbit asks, “Does it hurt?” And the Skin Horse says, “Sometimes.” 

When asked if it happens all at once, the Skin Horse reassures him that it happens over time when you’re ready: “Generally, by the time you are Real, most of your hair has been loved off, and your eyes drop out and you get loose in the joints and very shabby. But these things don’t matter at all, because once you are Real you can’t be ugly, except to people who don’t understand.”

It must be said that Woods dictates the entire passage verbatim, not missing a word. (“To the extent that I have a religion, it’s this passage,” he says.) But what’s the connection? 

“The thing I like about acting is that you’re trying to sort of love creatures into existence,” he says. “Even in a half-hour comedy, you’re trying to care about these people enough that they become real to the viewers, and that then the viewers care about them enough that they become real, too.” 

To the suggestion that it’s remarkable that he doesn’t play assholes, as so many of his comedy cohorts do, he protests that he doesn’t believe in assholes. Everyone has mitigating circumstances, he says, and are doing the best they can. 

He brings up an interview he once read with the actor Mark Rylance. Rylance quotes something his mother told him while growing up, that there are two kinds of people: those who think there’s enough to go around and those who think there isn’t.

“I think there is an attitude about empathy, that it is somehow like a finite resource and you have to hoard it,” he says. “That you have to be very selective about who you expand your compassion to because you’re going to run out, or there won’t be any left for you. I think the thing that I like about acting is you get to be sort of an empathy slut.”

He laughs at the term he just coined. 

“You’re not hoarding it. You’ll curl up with any character who comes your way and try to love them and empathize with them. And I guess my own personal experience is that the more you’re able to empathize with people, the more they’re able to empathize with you, and the less alone you feel.”

It bears pointing out that this is the second time in a major interview that he is brought up an existential children’s tale as a metaphor for his work. 

Speaking with GQ at the time of Silicon Valley’s ending and Avenue 5’s launch, he described his character on the HBO comedy, a well-meaning customer service agent who lacks certain people skills, as a man struggling to connect in the same way as the characters in Toy Story 3 do at the film’s heartbreaking climax, as they’re facing near-certain doom in an incinerator.

He laughs, making a bit of a “yikes” expression as he points out that The Velveteen Rabbit ends with the toys being burned because of scarlet fever. “I guess everything I love ends with toys being thrown into the fire.”

Woods knows it’s going to sound weird—he warns me as much—but he doesn’t remember getting tall. It’s not something he really ever experienced about himself. 

Of course, he is tall. It’s the first thing you notice when he walks into a room. It’s a central element to his characters and the awkwardness they give off, people who don’t know what to do with their bodies and the space they occupy. (On cue, Woods accidentally knocks over his Virgin Mary while gesturing with his arm.) 

At one of the first acting classes he took, the teacher told him that he doesn’t “own” his height. “I was like, ‘I don’t know what that means, but intuitively it sounds true.’” 

While he’s always been ambivalent about his height, he’s aware that when you’re physically tall, you’re kind of always in the way. “Sometimes people are complaining about manspreading and I’m like, I totally get it. But also if you’re this, like, weird beanstalk, it’s hard not to be taking up someone's space by accident.”

In real time as he’s talking about this, he’s connecting how these feelings have maybe influenced his comedy, specifically his approach to Jared on Silicon Valley. “I think because I felt like, for a lot of my life, I had the habit of sort of minimizing myself in certain ways, I was like, what if I took that that impulse in me and just cranked it up to the max? Maybe that would be funny.” 

When you’re very tall and pale, there are the “Lurch” comments and the “Ichabod Crane” comments, and other more uncouth descriptions that made Woods avow early in his career to steer clear of Twitter and internet comments. But occasionally, you’re confronted more directly than you’d like. 

He recounts a particularly upsetting example that happened when he was shooting the comedy Spy with Melissa McCarthy in Budapest. One night he was walking down the street and it was clear that he was going to have to pass two sex workers in order to get back to his hotel. He noticed one glance at the other, like, you want to take this one? Then the other one sighed. 

“Then the first one…” Woods starts, getting worked up telling the story. “You know when you get up to go do a chore you really don’t want to do? Like you have to go shovel snow or something. She got off of the wall and kind of lumbered over like, fine. She’s like, ‘Hey baby.’” Even now he’s baffled by the whole encounter. “I was feeling like I was being found inadequate by the sex worker. No one told you that you had to pitch to me. It was just like the most reluctant like, come on of all time.” 

When he looks back at Gabe, or Jared, or now playing Matt on Avenue 5, he can recognize how he’s used whatever it was that the Hungarian hooker saw that made her sigh and turned it into fully realized, very funny characters—maybe even without realizing it. He’s good at being awkward, even if it’s something he’s actively tried to extricate from himself in real life. 

“It’s sort of like when you go to a restaurant and it’s Sunday night and they’ve got a special, and it’s clear that they’ve just taken the ingredients that they have and made the best thing they can out of them,” he says. “I kind of feel like the ingredients in my kitchen are like insecurity and a certain amount of loneliness. That’s what I had in the fridge, right?”

“So for those characters, I sort of was calling on my available ingredients. And now as I’ve gotten older and happier, to be honest, and more sort of comfortable in my own skin, I find myself gravitating to characters who are more motivated by love than terror.”

He recognizes that he’s at some sort of fulcrum moment in his career and his life. Calling it a turning point would be paying it too much attention. But the fact is that Woods moved to Los Angeles 10 years ago. The biggest project of his career, Silicon Valley, just ended. New things are beginning, with Avenue 5 and Downhill. He’s 35. He’s evolved. 

“I used to think that I was auditioning for my self-worth all the time,” he says. “That if I didn’t do a good job, that it meant something really bad. I actually think it made me worse at my job.” 

It’s only recently that that paranoia stopped, and thank God, or The Velveteen Rabbit—whoever it may be—for that. “There’s so much more room in my life now for other, better thoughts. I’m not caught up in this negative narcissism anymore. It’s the part of growing up that I really like.”