Great Expectations: Connor Jessup

Connor Jessup wears Prada

“I think I have become much more reluctant to self-define because I've now seen so many different versions of myself,” says Connor Jessup over the phone, over 3,000 miles away in the english country-side.

Words by Dio Anthony

Jessup, 27 has rented a cabin in a quaint town outside of the bustle of Londontown, to write, reflect and sit with his feelings after a whirlwind year, that included 232 days of filming his series Locke & Key. On paper it sounds like a page right out of a movie––and he loves movies. He’s poised, witty and has a mind that seems to stimulate whomever’s in his presence, while working at breakneck speed––a term I learned from him. Speaking to him is a unique experience. He uses words only natural to an avid reader and speaks like a kid whose vocabulary multiplies by the day, because he’s always buried in a book. That’s because he is. With nearly 4,000 miles of land and of water between us, I attempt to connect with him for a fruitful conversation. What I get is so much more than a simple connection, but a sensible, mindful listener, completely grounded in the here and now. He enters the call––

DIO ANTHONY: Connor?

CONNOR JESSUP: Hi, how’s it going?

ANTHONY: Is someone else coming on the call with us?

JESSUP: Oh. Is there?

ANTHONY: I guess not. I’m used to having someone listen in on my conversations.

JESSUP: [Laughs,] to stop me from saying something..

ANTHONY: No, usually to stop me from asking something. So this is nice. I know you’re a huge book-worm, which is partly the reason why I’m so excited to pick your brain. What’s the one book you are quick to recommend to anyone once asked?

JESSUP: It really depends on the person and the mood and where I am on that day. But,  something I've been really excited about in the last few months especially is this series of comics called Heartstopper by an English author named Alice Oseman, that are so brilliant and kind, and healthy. They're these beautiful romances. It fills me with so much happiness that young people have access to these sorts of stories now that are not riddled with angst and doom. You know, there's a sense of community and just healthiness that keeps coming to mind when I think of those books. So I proselytize for Heartstopper nonstop. I’ve also been on a major John Berger kick recently. I love him so much. He's beautiful. A Late English, art critic, novelist, painter, poet, sort of all around polymath. A beautiful writer with everything he writes about. I read a book of his called Photocopies on this trip that I'm on right now, which is so beautiful. These little fragments, and little stories based on photographs. I was very moved by it, and continue to be.  There's always something new floating across my life. 

ANTHONY: That’s great. I like to ask big readers this question, being a reader myself. I read Tara Westover’s Educated years ago and it’s the first book I recommend when someone is looking for suggestions.

JESSUP: I still haven't read that. It's on my pile at home actually.

ANTHONY: I’m so excited for you. People always ask me if it’s fiction once I suggest it. It’s not, but her life story is remarkable, and so it reads like fiction. You know what I mean? 

JESSUP: Yeah, for sure. I feel the same way about something I’ve been reading right now. Do you know Tove, Jansson? She's a Swedish author from Finland, who is most famous for creating women’s comics, but she's also a wonderful novelist. Her most famous novel is a book called The Summer Book, which is just unbelievably beautiful and spare and tender and all the things we like. But she was a genius and I'm reading right now this thick volume called Letters From Tove, which is just her collected lifelong letters to her family and her lovers. They’re so beautiful, and I've been reading them kind of in between other books and they are these little gems of warmth and life. So, I always try to turn people onto Tove, like you’re doing with Educated.

ANTHONY: Thank you! You’re so well-read. I already have two three great pieces of art to add to my own reading pile. This is a really simple question, but I’m curious as to how you’d answer it. Why do you love to read so much? 

JESSUP: I mean, who knows? Why do people like music? Why do people like to dance? Why do people like movies, you know?

I was such a reader when I was young and I really got lost, like so many people do in these other worlds. There’s this companionship that you could feel, not only with the characters, but with this voice, this person who you would probably never meet. But in that moment, when you’re in their book, you feel so intimate with them. That feeling was such a high for me. When I was a kid, I loved fantasy books and the escape they provided. As I got a bit older, I kind of fell away from reading for pleasure for a few years, because I was reading a lot for school. I think I got burnt out on it. In the last five years or so, I've really come back to it and realized that–– it's one of the very few things I can do in my life that no matter where I am or what I'm reading I never regret the time I spend reading, you know? 

ANTHONY: I absolutely know!

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JESSUP: I can regret movies that I watch. I can regret scrolling on my phone. I can regret people that I'm with. I can regret most of the ways I spend my time. They are vulnerable activities to be a part of. Regretting reading is just not one of them. No matter what it always makes me feel a little bit better and a little bit fuller. And that, I think, is a real gift. So I've tried to jump onto that. You know, I also have a bubble. I come from a very specific background and the range of my experiences is limited to what I’ve done, who I am and where I've been. Reading is such an amazing rich window to do much more than that. It's a very important part of my life. 

ANTHONY: Describe your bubble to me?

JESSUP: I mean, I grew up very upper middle class. In a white neighborhood in Toronto. I went to a primary school that probably had 600 kids. It’s tiny, but it’s quite normal for Canada. I remember when I heard of schools having 1500 or 2000 students, it was hard to believe. So, that was quite ordinary. But of the 600 students, I think there were probably about 10 people of color. That was very much the dynamic that I had grown up in. I've been working on sets since I was 10 or 11 years old. I didn't go to college. A lot of the ways that people break through or are exposed to radically different sorts of people and worldviews just were not part of my life. That’s my bubble.

ANTHONY: You're very eloquent and well-spoken for something who didn’t attend higher education, as they call it. 

JESSUP: Thank you!

ANTHONY: Let's talk about films. I’m obsessed with movies, and I know you are as well just from the things you post on your instagram and the things you’ve done.  What’s the last film you've watched that left a lasting impression on you? My most recent was Tick..Tick..Boom. It just kind of spoke to my heart.

JESSUP: Right.. Interesting. Let me think. I’m in the UK right now and a couple weeks ago I was in London. They were having a retrospective of Wong Kar-wai at the BFI.  All of his movies have been restored recently. I saw with some friends, In The Mood For Love, which I had seen a couple times before, but I had never seen it in a theater. For some reason at that moment, it completely overwhelmed me and I was rocking back and forth in the seat, and I was crying and totally out of my mind.  My friends told me that at some point they stopped watching the movie and were just watching me. I had a really physical response to the movie, which is not that common and it was an amazing, very moving, very lasting experience.

ANTHONY: That sounds so lovely. 

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JESSUP: It reinforced the wonderful thing about all art, which is that even something that you have seen before, or that you feel like you know, can sneak up on you. The movie hasn't changed at all in the three times that I've seen it, it's exactly the same series of cuts and performances and everything. You know, but I've changed. And for whatever reason in that moment, it really, really struck me over the head. So that one, for sure will sit with me for a while.

ANTHONY: That’s such a good point. The idea that the movie hasn’t changed, but you have. 

JESSUP: Yeah. Which is also depressing I find, because it makes you realize that not only are there thousands of movies that you haven't seen and can never hope to see, but even the movies that you have seen need to be rewatched because they can still be new, you know? I'm guilty of that sometimes. I was such an obsessive movie watcher when I was a teenager. So sometimes a movie will come across or there's a new screening or something and my immediate reaction will be like, no, no, I've seen that.  Then I realize–– Like, wait, Connor, you saw that when you were 17, give it another shot. Often those experiences are really revealing and totally new. 

ANTHONY: That's so incredibly true. I was actually going to ask you if there was a film you've watched lately from this first time that you’d wish you could see again for the first time. You got ahead of me with your thoughts and I’m so glad you did.

JESSUP: There's so many movies that I wish I could see for the first time. Every movie that I love, I wish I could see again. But then again that’s also interesting. I think we put so much value on novelty or the experience of watching or reading something for the first time. There's obviously a thrill in that, but there is something that I've come to appreciate more about the deepening relationship you can have with a piece of art, the more you encounter it.  You know, that first time is great and there's all sorts of emotions that can be very specific to that. But, there's all sorts of emotions that can only be unlocked later too. You know?  I'm happy with the things that I've seen, and I haven't seen. I'm sure that there are so many movies that will change my life that I haven't seen yet. 

ANTHONY: I'm always waiting for a movie to change my life.

JESSUP: I feel like I go into every movie hoping that it'll have that effect. 

ANTHONY: You're always sharing good pieces of art on Instagram. What are you currently obsessed with on the internet right now? 

JESSUP: The Internet! Oh my God. I mean, I'm obsessed with the new Adele (30) album right now.. Obviously I've been blasting that on loop. But which functional homosexual isn't? I mean, that's the current obsession, if I'm being completely honest. This thought isn’t very unique, but God, it's good.

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ANTHONY: I think that’s a really good answer. I was talking to my friend about this very album yesterday. I feel like Adele's albums hit differently. For starters, the fact that she names her albums the age that she's in is so poetic to me. I remember listening to Chasing Pavements on her album 19 when I was 18. It just really hit me. Now when I listen to that song, it hits me a little harder because It reminds me of those old feelings. Now she’s talking about marriage and heartbreak, and I’m not married, haven’t been divorced or currently going through a heartbreak.. But this idea of her albums serving as little books of her life is something I just can’t appreciate enough.  

JESSUP: Oh yeah, I totally know what you mean. One of my favorite movies is this Taiwanese movie, and there's a great line in it where the main character is talking to a friend about his childhood and he says my father used to play all of these songs. I never understood it. Then finally I fell in love and suddenly all my dad’s music meant something [laughs].

ANTHONY: Wow.

JESSUP: I feel like that's very much an experience that we all have with art in general, which is that––sometimes as an artist, you're reacting on instinct to whatever's happening in your life and your influences. Five or ten years can pass and you look back on the thing that you made, and it means something different to you than it did when you were making it.  I think that's fascinating too. 

ANTHONY: The power of context

JESSUP:  Exactly. 

ANTHONY: What’s your favorite track right now on 30? 

JESSUP: My Little Love, oh my gosh.

ANTHONY: Me too.

JESSUP: They're all great. To Be Loved is obviously maybe the best song on the album. It's an overwhelming accomplishment, but My Little Love really just…. I had a listening party with friends the other night when it came out and that one had me...I was f#cking a mess. I loved it musically and it felt so honest. The outro when the voice recordings of her talking about her loneliness, it really hit me and I really loved it. It also came at exactly the right place in the album I thought. That's the one that I've listened to the most..

ANTHONY: The vulnerability factor there is really impressive…

JESSUP: For sure.

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ANTHONY: It was definitely one that I was instantly like, repeat, repeat, repeat. I also think it's just so powerful. She's talking about this very particular situation in her life. I don't have children and I've never gone through a divorce, but I felt it just the same, you know?

JESSUP: Yeah. I also think when I was listening to it, for the first time I had this thought towards the end, because obviously she has all those voice recordings with her son threaded throughout the song. I had this image in my head when I was listening to her son, or him being older listening to it. Which for some reason struck me really emotionally, that this was something that he would experience. I don't know him. I don't know her. I don't have any connection to them as people, but just the idea of being 15 or 20 or 25, and being able to listen to that and have that sort of relationship with your mom. I don't know, it really moved me.

ANTHONY: Yeah. I'm mushy inside just thinking about it, honestly. Really good stuff. So, what are you doing in the UK right now? 

JESSUP: Yeah, I'm in Cotswold right now, which is in the countryside, kind of near London. I've rented a cottage for the last month to try and get some reading and writing done. 

ANTHONY: How’s that?

JESSUP: Oh I love it! But I've been going back and forth. So I've been spending a lot of time in London and this is actually my last week right now in the cottage. So in a few days, I will go back to London for a while.  I'm here until almost Christmas. 

ANTHONY: It sounds so cinematic.  What's life been like in the cottage? In the UK generally?

JESSUP: It's been a mix. It's very cute and quaint and peaceful and it's been restful, which is what I was looking for. It's also been a little lonely at times because I'm in this cottage by myself, in a town where I don't know anyone. But in a way, especially when you're trying to write, this is something that I've learned painfully–– that really the currency that you're working with is boredom and loneliness. And if you're not willing to spend a bit of boredom and loneliness, you're not gonna get anything done. So in a way the loneliness, as tough as it is, is by design. That's what I was looking for. It’s been a success in that way.

ANTHONY: Do you mind if I ask what you're writing?

JESSUP: Yeah! I'm writing a movie. I've been working on it because I've made a whole bunch of shorts and a documentary and music videos. I've done different stuff as a filmmaker, but I need to make a feature. It's in me and I need to do it. I've been in actor mode for a while. Now that a year of shooting Locke & Key is done, I was looking to get a little bit of space to work on my own stuff.

ANTHONY: I feel that. Has being there made it easier to write?

JESSUP: Yeah and no. It depends on the day. Writing never comes naturally. Maybe it does for some people, but I think for most people, it doesn't. It's always pulling. I think you get little wins from things that just come up in your head and you have to go with it. It's been mixed, but it's always mixed. I used to beat myself up a lot more about it being mixed. I always had these high expectations, romantic visions of whatever or wherever I was in my life. And accepting that it's always going to be a little bit hit and miss and not flagellating yourself for failing one day or for taking a couple days to just read. It's healthier in the long run.

ANTHONY: I think it's interesting that you mentioned you have romantic views of where you are in your life. We are the same in that sense. I’m a hopeless romantic for life. It's easy for me to see that you're a romantic for life as well. Just by your persona online–––which is perhaps part of another larger conversation, because we’ve just met. Yet I have these thoughts about who you are, and the way I perceive you. I’m the type of guy that strikes up a conversation with a stranger. Are you the same way?

JESSUP: I think it depends. I think I have become much more reluctant to self-define because I've now seen so many different versions of myself. There are moments when I love talking to random people in cabs and bars and there are moments when nothing sounds less appealing.

ANTHONY: [Laughs].

JESSUP: You know what it’s like..when people try to start conversations––I'm like, yeah. Okay. Cool. I think the contradiction of that is how most people experience things, and trying to hold yourself to something else can be troubling.  I caused myself a lot of anxiety for a while by trying to hold myself to an image that I had of who I was or who I should be. Those images come from lots of places, you know, they come from the books and movies that we watched growing up, and from things our friends or family tell us about ourselves. People will observe you and say, oh, you're so blank or you're so this. Then you integrate that into who you are and you start to believe it. For example, I mean, this sounds douchey beyond words, but, when I was a teenager, around 15 or 16, people were always like, oh, you're such an old soul.

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ANTHONY: Such a classic thing said to so many people.

JESSUP: It's like the cringiest  thing you could possibly say. But I think for a long time, I was like, oh yeah, that's what I am. I should be that. So I started to define myself and make choices and not do things because that was the image I had of myself. Only in the last few years have I realized that I actually have no relationship to that. That there are so many things I like, or don't like that are not bad at all. Putting yourself in a box is just futile, you know? 

ANTHONY: Yes--wow. 

JESSUP: So that's a long and ponderous way to answer a very straightforward question.

ANTHONY: That was an amazing answer I never could have imagined or wished for. I feel like I'm on a Super Soul podcast episode right now. I love.

JESSUP: [Laughs].

ANTHONY: Earlier you mentioned the cabin you were staying in being a restful space. Which feels like a natural thought considering you’ve been filming back to back seasons for an entire year. That feels like an untrue statement. But it’s not..

JESSUP: Yeah. It was crazy. We shot not on and off–– but literally straight. Seasons two and three, back to back like you said. We started shooting last September and shot until this September. With the exception of Christmas and a small, two week hiatus between seasons, we shot straight through a year.  I think it was like 232 days of shooting or something. Which is by far the longest hall that I've ever done. Considering that most independent movies, for example, you shoot for like five or six weeks. That's a very different timescale.

ANTHONY: What is that like for you? You're going to set every day. It feels next level.

JESSUP: It is, and it was a lot. But honestly, because like you said, the way TV works and the fact that there's so many characters and there's different plot threads, you're not working breakneck speed every day, all the time. There is a point after a few months of shooting where it becomes, I hate to say automatic, but it does become a little less stressful. There's been movies that I'm in where after six weeks of shooting, you feel like you're dead by the end of it. Like, you cannot move, you know?  This is a much more manageable speed. But a year of doing anything can be a lot. You see the same people every day, which is really nice, but that becomes your whole life too. I love the show and I love all those people and I love that atmosphere. It was an amazing way to be social and creative during the heart of the pandemic. So, I'm really grateful for that. But, I definitely was ready to go onto other things. 

ANTHONY: Of course. When you started acting at 10 or 11 years old, did you think that today at 27 this would be the career you’d be in? 

JESSUP: I didn't think about it once. When you're 10 or 11, you're not thinking about being 27.

ANTHONY: That’s very true! I ask this only because I can see you thriving in a number of different careers...

JESSUP: Honestly I don't have a lot of memories of really thinking about that intensely when I was younger. I think the first few years I was an actor, if you had asked me what I was going to be when I grew up which, you know, people love to ask kids. I think I would've said a Doctor or something like that. I don't think I would've said an actor because no one in my family was in the arts. I was pretty good at school. I liked science. So I think that was the answer I gave. Then around maybe the age of 16, I started to work more consistently on bigger things. It became a more active part of my life and that answer changed. But really, because of the way jobs work as an actor, you can't control it, and you can't control how long things last or where you are. It really did just pull me along. One thing led to another, which is something that in a way I've been reckoning with, I think in the last couple years. I found myself at this point, in my mid to late twenties, with a life and with a career that wasn't really the result of choice. Do you know what I mean? 

ANTHONY: I do, yeah.

JESSUP: I love it so much. It’s made my life rich and introduced wonderful, wonderful people into it. But I do think there's a point, even if you love what you're doing, where you have to start making choices. It's something that I've really started to think about more.

ANTHONY: I’m learning from you, honestly. You know..I watched an interview with you where you talked about how you didn't really come from a very movie watching family.

JESSUP: Right.

ANTHONY: Yet, you were watching all these films and on your own. This was my experience growing up as well. My mother is a therapist. She’s not much of a creative person outside of her cooking––so I really just didn’t have many people to talk to about these things. She appreciated it, but she didn’t understand movies like I did. To me it was really my first window into the world. When you’re not sharing that with someone, it’s a different experience. 

JESSUP: My mom loves movies and she's always been very supportive, but when I was growing up, I wasn't exposed to a wide range beyond what most people are. It wasn't until I was about 14. I met some people who started to show me things.

JESSUP: I'm lucky that I'm probably the first generation of people who, when they hear about a movie or read about a movie, can easily find it that day if you wanted to. There’s all these amazing resources. Because I was working as an actor at the same time this was happening in my life, I was watching movies and then going to set and working. There was always someone to talk to. I never felt sequestered away from it. There was always some interesting older actor or some camera operator or cinematographer who would listen to my pubescent ramblings. I was lucky that way. I think that also drove the enthusiasm and gave it fuel, you know? 

ANTHONY: Yes! I know and I love it!  I really do. Okay. So, the same day of your American Studies shoot, you flew to Greece. I know you mentioned the trip in another interview, but I'm a big fan of traveling alone. I was wondering if you had any experiences, while abroad, that really charged you up. Something that made you feel like going on this trip was the right choice?

JESSUP: Yeah... Interesting

ANTHONY: I'm superstitious in the sense that, and this might be silly––but I think that when you're somewhere and a favorite song comes on, it’s the universe's way of telling you you’re exactly where you’re meant to be. Especially when it’s an obscure song. 

JESSUP: I would probably have to think about that a bit more, but I think there's so many things that happened when I was in Greece and then here in England. Maybe this sounds depressing, but the main thing that I've been grateful for about the choice that I made to do that, which obviously is a great privilege to be able to choose to do is––but I have a lot of stuff to process in my life right now. Stuff that, because I was working and I was busy, I didn't have space to really sit with, you know?  I think I very easily could have just moved on to other busyness and kept kicking that down the road. Because I chose to travel alone for a long period of time, I was really forcing myself to sit in it. Which is maybe not the romantic vision of traveling in Greece that people have, but it was really important for me and continues to be important for me to have this time to work through some stuff. That is the main reason why I'm glad that I've done this.

ANTHONY: Deep.

JESSUP: It’s not quite as sexy as being like, I saw a reflection of light off the top of the Parthenon and I was changed, but it is true.

ANTHONY: That's actually what I was searching for. Thank you. What's the town you're in like? I'm picturing this very cute little cottage..

JESSUP: That’s exactly what it is!

ANTHONY: Do you go out and speak to people? Is there anyone around?

JESSUP: Yeah. I mean, it's not that remote. It's in this little town called Bourton on the Water, which is this quite famous touristy town. It's very quiet, but it's not very remote. I'm not in the middle of the woods. There's a whole bunch of restaurants and pubs right around the corner from me. Lots of thick accents, and really kind, lovely people. I know who I know now. I go into a restaurant and they bring me a tonic without me ordering it, that kind of thing.

ANTHONY: That’s the vibe I’m thinking, yeah. This cute little town where everybody knows each other.

JESSUP: Yeah. That's very much it. Also, it's kind of a touristy town, but because it's late November, it's off season. So it's quiet now.

ANTHONY: Is that your go to drink?  A gin and Tonic?

JESSUP: It never was, but for some reason it's become it. I don't know why. I'm not a big drinker, but, when you go through moods, you know.. I would usually order a glass of wine. Then I found that, and maybe this is a sign that I'm getting old, but I realized It would affect my sleep [laughs]. So now I order a gin and tonic, or a vodka soda–– like a college girl.

ANTHONY: [Laughs]. In what way would it affect your sleep? Would it help you or stop you from sleeping?

JESSUP: Well, I would fall asleep easier, but then I would wake up, like three or four hours later if I had more than one glass of wine, feeling hot and sort of sticky and a little blurry and just not great. So I realized that the pleasure I got from two or three glasses of wine was not worth the discomfort of a bad night’s sleep.

ANTHONY: So funny. So, when you're going out to this pub you mention––do people know who you are? Are you under the radar? Or are people just not that interested? 

JESSUP: A mix? The thing about small towns is that people have time to really look at you. In a way that they don't in the cities. I've actually found that more people here have identified me than in London, for example. But everyone's super chill and no one really cares. I'm not Beyonce. People are like, oh, you're, you're in that thing, aren't you? And I'm like, yeah, and they’re like oh, cool. So, what do you wanna order? 

ANTHONY: [Laughs].

JESSUP: That's the energy that I like anyway, so it's been chill. 

ANTHONY: I have two last two questions––What's the last thing you Googled?

JESSUP: The last thing I Googled? I Googled Taveners Fruit Drops, which is a British candy. My dad's girlfriend texted me saying that he had been feeling nostalgic for this English candy that he had been given once when he was a kid. She was wondering if they still made this candy so that we could give it to him for Christmas. So, that was my last Google, these Taveners Fruit Drops.

ANTHONY: So sweet. The next one is––and I just thought about this right before our call. I think it’s going to be one of my new staple questions. If you had to name this era in your life, what would you name it?

JESSUP: That is such an interesting question...

ANTHONY: Thank you. Think of it as a movie title..

JESSUP: I think maybe––Interlude.

ANTHONY: Interlude..I like that.

JESSUP: Interlude. Maybe I'm wrong though--that when I look back at this period, it will seem like transition..

ANTHONY: Dude, honestly, I had a really good time speaking to you.

JESSUP: So did I. So much fun. Thank you for the thoughtful questions. 

ANTHONY: Of course. Good luck with your writing, and everything in life too.

Written by Dio Anthony

Photographed by David Urbanke

Styling by Yael Quint