‘Red Oaks’ Stars Craig Roberts, Ennis Esmer, And Oliver Cooper On Working With Amazon And Going Back To The ‘80s

It’s 11 AM at The London Hotel in Manhattan, and I feel as if I just crashed a reunion party. It’s the morning of the premiere of Amazon Prime Video’s throwback comedy Red Oaks, and the online shopping giant turned savvy series producer is hosting a round of sit-down interviews with members of their latest original series. Welsh up-and-comer Craig Roberts, Canadian jack-of-all-trades Ennis Esmer, and stoner-esque buddy next door Oliver Cooper — along with their reps — are crammed in the entryway of their hotel room laughing hysterically at what’s surely an inside joke while waving me inside. The Today Show, where their co-star Jennifer Grey just made an appearance, is blaring on the TV in the background before someone shouts about how loud it is. When I go to sit down with Roberts, Esmer, and Cooper, it’s a game of awkwardly chivalrous musical chairs with this accidental comedic trio, who carry similar demeanors both on and offscreen: Roberts the soft-spoken wit, Esmer the jokester, and Cooper the teddy bear.

Premiering today only on Amazon Prime Video, Red Oaks follows introvert David Meyers (Roberts) through the summer of 1985 and his bumpy journey of self-discovery at the titular country club. Produced by Steven Soderbergh and David Gordon Green and created by Gregory Jacobs and Joe Gangemi, the ten-episode first season feels more like an indie from yesteryear, equipped with short shorts, leotards, and a delightfully ’80s soundtrack. There’s an innocence to the series carried by a lead reminiscent of The Graduate‘s Ben Braddock and a supporting cast of misfits who manage to uphold one of this fall’s strongest ensembles. In addition to Roberts in the lead role, characters played by Ennis Esmer and Oliver Cooper provide consistent comedic relief at Red Oaks Country Club as Nash and Wheeler, who, like David, are experiencing a little self-discovery of their own.

I sat down with the trio to get the scoop on what it was like going back to in time, working with renowned film directors on a streaming-only series, and how much they love their fellow Amazon show, Transparent.

Decider: So how was it going back in time to 1985?

Craig Roberts: It was awesome. There was no Instagram. We couldn’t survive really.

Ennis Esmer: Yeah, there was nothing to do.

How were the short shorts?

EE: Big fan of them.

Oliver Cooper: I didn’t have to wear the short shorts.

CR: You had one outfit.

OC: Yeah, pretty much. For me, it was one of the easiest jobs in terms of hair, makeup, and wardrobe. I never had to do anything [laughs].

EE: I was seven in 1985, and that’s how I actually dressed. I have pictures of me that age just wearing short shorts and golf shirts. That’s how my parents dressed me. I was a pretty slick little kid back then.

Has it been strange waiting over a year for the series’ release?

EE: Personally, I found it really weird because in the interim I got super buff, so I had to lose like forty pounds of just sheer muscle mass to get back into the role because it works chronologically. Obviously I put it back on, plus ten [laughs].

OC: I didn’t gain muscle, but I had lost some weight and I had to gain it back before we shot. Throughout the show I kept gaining it. But I hear that all the time online: people are like, “It’s been so long!” But I guess for me, it didn’t really feel that long only because we shot [the pilot] last summer.

Does waiting take you out of the character at all?

CR: It didn’t for me, no. It’s strange that the conversation is still completely open as well, because the pilot still exists online and people can still watch it while we’re making the season, which is kind of interesting.

EE: I did have to practice the accent again because I had stopped talking like that. I’m also curious to know how many people will watch the pilot episode now, because the whole way it was marketed was so different. They were just pushing the pilot, and now there’s an entire season, so people who may not have had Red Oaks or any other Amazon Prime shows on their radar might just go, “Okay, I’m just going to watch it,” because it’s a whole thing now.

OC: It was kind of like shooting a movie. When you do a movie, you shoot it and like a year and a half later the movie comes out. It’s only been a little over a year since we shot the pilot, and now the whole season is coming out.

Other than the waiting game, are there any differences for you three between working on a network or cable TV show, a film, and a streaming-only series?

CR: I think the big difference is the fact that it’s Amazon. It seems to be the case that the creators Joe [Gangemi] and Greg [Jacobs] have just been able to completely project their voice and it’s not being altered with because they have so much freedom and have been trusted. That’s the big difference I’ve seen.

EE: For people who don’t know Joe and Greg — when you consider names like Steven Soderbergh and David Gordon Green — clearly Amazon’s mandate is picking people whose voices they can trust and picking those visions they want to see. It’s been said that they want to make this like a five-hour movie, so to go into it like that production-wise — I mean, they had the whole season sort of flushed out. And while we were doing the pilot, they had ideas of where they wanted it all to go, which is great because so much stuff that’s introduced in the first episode — it doesn’t just go away. It’s a serialized show like so many great shows are.

OC: It does feel like a movie. In my experience, this show in particular, every episode feels like you’re making a movie. We had all these film directors. We had David Gordon Green, who’s done TV as well, but I guess the way they go about it feels so detail-oriented. Every episode felt like we were making little, thirty-minute films.

EE: The added bonus of working with people like Amy Heckerling and Hal Hartley is that it’s a film education, too. I had just started watching Transparent when we started shooting this, so when I found out Nisha [Ganatra] was directing, I was just speechless.

OC: This is an amazing group of directors we got to work with. It was really cool and interesting to see that everyone had such a different style and voice, but at the same time, it still feels like the same show.

Speaking of Amy Heckling, she directed Episode Seven, “Body Swap.” Craig, how was it getting into Richard Kind’s character?

CR: Awesome. But [the episode] does feel weird. It stands out as sort of this heightened journey where they both find themselves, which I find really cool and obviously very eighties. I’m very grateful it was Richard Kind because he’s such an idiosyncratic character. It was very fun. Although my back was hurting [laughs].

EE: When you think of movies like Like Father Like Son or Vice Versa, they all wrap up. And you’re like, hold on, wait a second: the kid got his dad fired now and the kid has to go back to school after the dad humiliated him or something like that. Whereas, what I love about that episode, is that it shows the aftermath of what happens, and I just feel like that’s never really been done before.

CR: And it’s very clever to touch on whether it actually happened or not. It’s not really explicitly said even though they slightly learn things about each other. We don’t really know what went on because it’s left as kind of ambiguous.

How does it feel having a pilot you’re starring in get voted on?

EE: It’s interesting because Amazon tracks votes, they track reviews, they can track who shared it with who and how many times you watched it.

OC: When we were doing the pilot, it felt really new because Transparent hadn’t even aired yet. I think Amazon had Alpha House and Betas come out, but I was really unfamiliar with Amazon shows until they all just kind of exploded within this last year with Transparent, Bosch, and Mozart in the Jungle.

Is there anything in particular you’re watching that you’re really into right now?

OC: I’m kind of late to the game but I’ve been watching Breaking Bad. There are so many great shows, it’s hard to keep track. I just watched Transparent recently.

CR: Transparent is really remarkable. It’s so freakin’ good.

EE: I watched it completely out of order and it was still fantastic. I’m Canadian and we don’t get Amazon Prime Video up there, so I used my connections at Amazon and was sent a link, but for some reason it was listed out of order and I only caught on to that about five episodes in. It speaks to the quality of the whole show. It’s incredible and there’s so much going on and so much story that starts in one episode and finishes in another, but it worked.

CR: With Red Oaks, it felt like, although the stories did end on something, each felt almost like an eventful vignette.

EE: I mean, there are cliffhangers, but not in the same way on TV where it seems like at the last second [of an episode] something crazy happens that makes you have to watch next week. Not that there’s anything wrong with that type of show, but there’s a flow to these where it doesn’t have to end on this crazy note… It doesn’t really matter that it’s 1985. It’s the summer. That transformative summer everybody has in their life, that’s a real thing. No matter where you’re working or what it is you encounter, your first real group of people in a new environment where you kind of lose sight of who you thought you were — that sort of stuff is all in there. They definitely sacrificed cute endings for things that were open-ended.

CR: One of the references for Red Oaks seems to be The Graduate. And it is kind of like that in the sense of the decisions that you make: are they right or not? You definitely feel that, especially at the end of David’s journey and seeing it through his eyes like Benjamin Braddock. Which is a great reference to have because The Graduate is a freakin’ masterpiece.

Stream Red Oaks on Amazon Prime Video starting today.

 

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Photos: Everett Collection