Photo: HBO

At the end of this week’s Silicon Valley, Haley Joel Osment’s virtual reality entrepreneur Keenan Feldspar appears grinning next to Stephen Tobolowsky’s Jack Barker in an advertisement for Hooli-Con. But the HBO comedy wasn’t the first time Osment—still probably best known for the iconic roles he played as a child, like in The Sixth Sense—worked with Tobolowsky. Their initial collaboration was on the Disney movie The Country Bears, though that time, Osment was playing an animatronic animal.

Keenan emerges as an unlikely antagonist. After he seemingly makes a deal to buy Pied Piper for $25 million, at the last moment he takes his company to Hooli, dashing our heroes’ hopes of going to the metaphorical Hawaii. Despite that, Osment finds his character more oblivious than underhanded. The A.V. Club spoke to him about that and his impressive beard.

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The A.V. Club: You’ve been doing a lot of comedy stuff for a while now. How did this role come about on Silicon Valley?

Haley Joel Osment: I just auditioned for it last fall and got the part and worked on it for the first few months this year. I’ve been a big fan of the show ever since it came out, and I’ve sort of gotten to know Thomas [Middleditch] through seeing some of his shows and through mutual fandom of the Los Angeles Kings. And I’d met Kumail [Nanjiani] before and everything, but this was the first time I’d gotten to work with them, so it was pretty exciting.

AVC: What interested you about Keenan?

HJO: I didn’t know a whole lot about the character because most of these shows keep things pretty tight to the vest. So I just read a pretty small scene of his, and then once I got the part, they revealed a little bit more about what he was all about and what his business was on the show and everything. A desire to feel good all the time is a really funny little quirk of his and leads to some great situations.

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AVC: Halfway through the episode, you think Keenan’s going to become part of the gang, and then you realize he’s very underhanded and sneaky. Was that something that was revealed to you right off the bat, or did you learn that as the characters did?

HJO: I don’t know if he’s underhanded, although it may seem that way eventually to the guys. Keenan is one of those people who—in contrast to the team on the show, where they struggle for years to get their ideas made and to be appropriately compensated for all the work they’ve done—Keenan is just someone who just got rich really quickly, and money is sort of no object to him. There are some people like that in real life who don’t understand the power they wield and just want the things they want and they want them now and don’t really care about the consequences. I think Keenan is somewhat guilty of that. He’s a little bit younger than the guys, and they put in more time, and Keenan just sort of had his first idea blow up really big, and it creates this unfair dynamic between them.

AVC: So you see the move to Hooli as cluelessness rather than maliciousness?

HJO: Yeah, just totally oblivious to the needs of other people, and whatever he thinks is awesome he assumes is going to be awesome for everybody else.

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AVC: There’s been talk that your character is based on Oculus Rift founder Palmer Luckey. Did you base him on anyone in particular?

HJO: No, I think one of the really smart things they’ve done ever since season one is obviously there are some real-life people that inspire these characters, but they never wanted to do emulation of them. Obviously, people like Steve Jobs and [Steve] Wozniak are sort of hanging in the background for these guys, but when it turns into Gavin Belson or something like that, they have their own character that’s independent of the real-life inspiration. I think they did that with Keenan, too, where we are familiar with how the VR market is working and some of the people who are involved with that, but the real comedy of Keenan comes from what Alec Berg and everybody have designed in the character and his pursuit of a good time and awesome stuff and just sort of obliviousness that I don’t think comes from a real-life person directly.

AVC: Monica tells Richard that Keenan is on thin ice because the tech is too large to fit on phones, which is where VR is going to become more accessible. Do you still see Keenan as oblivious or a bit of a bullshit artist with the tech?

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HJO: I think it’s a little of both, and I don’t think that he’s a bullshit artist in intentionally deceiving people. I think his flaws are just not having a deep understanding of what he’s doing and the consequences of what he’s doing. Yeah, I think it might be fair to say that with some of these technologies, some of these people are just accidentally the first in the door with something that becomes important for a different reason later on. I was talking to Thomas about this, too. For video games—Thomas and Kumail are really good gamers—it’s still a difficult proposition to get people to strap stuff to their face for more than a couple of minutes. After a while it gets a little tiresome to have this thing on your face. The Google Glass and everything didn’t become as ubiquitous as maybe some people thought at first. So there’s a gap that has to be closed between how awesome it is and how actually useful it is.

AVC: Part of Keenan’s look is his beard. Were you rocking that prior to the show or did you grow that as part of the way you wanted Keenan to appear?

HJO: I had grown that and my hair in general out for this show I’m doing on Amazon, Oasis, where I play a weed farmer in the future. As I started reading the script for Keenan—his Hawaiian shirts and the flip-flops and jeans—I was like, ”Yeah, this kind of raggedly look feels appropriate.” And when I went to the first table read, I didn’t know exactly what they wanted, and Mike Judge saw it and was like, “Oh, yeah, perfect, this works for Keenan.” I was like, “Perfect, I don’t have to shave.”

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AVC: In some ways, the beard does give this laid-back, jolly quality that goes along with his whole vibe, which is one of the reasons that the ending of that episode is so shocking.

HJO: You never think that that person is going to be anything less than chill.

AVC: In playing him, how do you walk that line? He is so chill, but he is also really happy with his money. He’s going to go kite-surf and get in touch with nature to make up his mind, but he’s going to make the most financially beneficial choice.

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HJO: The notion of self-care for people who have hundreds of millions of dollars, it doesn’t seem like a radical thing. It’s like, “I do need to fly around the world and kite-surf just to get my head in the right place.” That sort of behavior flies right on this line. I read this in a pretty recent interview with Mike Judge, where he totally nailed what the show is about, where he’s like, “In Silicon Valley, in the real world, will the Steve Jobs, idealistic, hippie vision prevail or will the newer, libertarian, money-centric culture prevail?” All these guys have kind of fallen on that line and within individual people—because I think with Keenan, yeah, he loves being rich but also has these sort of chill, holistic qualities, and they are sort of in conflict with each other. You can’t be that chill unless you are backed by hundreds of millions of dollars to allow you to relax all the time.

AVC: Once characters enter the Silicon Valley universe they don’t really go away. Is that something that you’ve talked about? Will that apply to Keenan as well?

HJO: I’d love to. I’m not sure what their plans are for season five, but it’s not Game Of Thrones. There aren’t a lot of deaths that you have to be scared of. I’m hoping that there is a future for Keenan.

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AVC: T.J. Miller is leaving the show. That news came out around the time your first episode debuted. There was a story in Vanity Fair that was looking at Keenan perhaps as a character that will—not replace Erlich, because there is no replacing Erlich—but will stand in as a figure on the show, especially given that it also seems that Gavin Belson has gone away for a time. Do you have any reaction to those sentiments that are floating around the internet?

HJO: I heard about it. I can’t speculate about what they have planned for the show, but a lot of my stuff that I already shot was with T.J., and he was really awesome to work with. As you said, even though Erlich’s gone, nothing can replace that character. Obviously Keenan was something they were creating last year before all this happened recently. You have people like Russ Hanneman who come in and add some different energy to each season, and Keenan will hopefully serve that purpose.

AVC: You were on Comedy Bang! Bang! You did the The Spoils Of Babylon and its sequel. How did you get involved in that world?

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HJO: I think Spoils was probably the first entry into that community and that world. I’m not a stand-up comedian. I’m not an improv person or anything, but I’ve always been a fan of that stuff. Once I did Spoils and started that relationship with IFC, that led to the Comedy Bang! Bang! stuff and everything. It’s a really fun group. They all work together in different iterations, particularly in the universe of Comedy Bang! Bang! between the show and the podcast and all of that. That style of comedy has become so influential across the industry. It’s just really fun to get to know those guys. And you learn so much, just listening to that podcast over all those years. Particularly Thomas’ episodes always seemed to crop up in the best-of at the end of year, because he’s just so funny doing his characters. It really gives you a good sense of what’s possible with all of that.

AVC: We saw that little bit of Keenan with Jack Barker. Are you working with Stephen Tobolowsky in these upcoming episodes?

HJO: Yes, I had some stuff with Stephen. He’s incredible. We were in the same movie—we did The Country Bears, like, 15 years ago, but my character was animatronic, so we didn’t have a lot of face-to-face interaction, so it was good to have that this time.

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AVC: Was that a connection that was made on set at Silicon Valley?

HJO: Yes we did. I got to talk to him about how Christopher Walken was the villain in that movie, so he got to do stuff with him. The whole six degrees from Kevin Bacon thing, as you get older it gets more and more intertwined.

AVC: Characters on Silicon Valley go from helping Pied Piper to being antagonists. Do you see Keenan in a role as the villain in the last two episodes of the season?

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HJO: I don’t know. I don’t think I would see him as a villain. He certainly wouldn’t see himself as that. But, yeah, changing circumstances flip around who is the antagonist from time to time. I think you’ll see some interesting reversals coming up as they get closer to breaking through.

AVC: You had some very famous roles when you were a kid. What are the reactions you get from people now that you are popping up on beloved TV shows?

HJO: It’s fun. It’s a natural consequence of going to school for several years and not really being in L.A. at all and going off and coming back and doing kind of unexpected characters that are really different than what I’m mostly known for in the past. Especially now that I’ve done a bunch of roles consecutively with a crazy beard or something or crazy costumes in Spoils. People are like, “I didn’t realize this was you until the end.” And as an actor, that’s some of the most fun stuff, when you can, for whatever reason, kind of disappear into a role.

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AVC: Is it a conscious choice when you’re seeking out roles to do these outlandish characters?

HJO: Yeah. They are very outlandish characters. And even though I wouldn’t classify Keenan as a villain, now that I think of it, a lot of the past couple of roles, including Future Man, which I am shooting right now for Hulu, I am kind of the bad guy. I think most actors would say some of the most fun roles are when you’re evil, and that’s been really exciting to be the bad guy in a lot of scenarios. Because when you’re 12, you don’t get to play the villain too often.