Last month, Sky Ferreira caught our attention when she released music videos for “Everything is Embarrassing” and “Sad Dream,” both directed by Grant Singer. Since we are The Music Video Database, it is literally our job to get excited about an artist releasing two music videos in the same month. However, since Sky and Grant are also collaborating on the short film IRL (Grant directs, Sky stars), we were particularly interested in their working relationship. The videos come at a bit of a transitional period in Sky’s career, and Grant injects a natural quality into these videos that is very effective. We talked to Grant about working with Sky, and collaborating with her on IRL and the videos for her Ghost EP.

Doug: You’ve done two videos this month for Sky Ferreira, and she also stars in your short film IRL. Where did your relationship with Sky begin, and how did you guys come to work on these projects together?

Grant: I was introduced to Sky by my friend Patrik Sandberg, who also wrote IRL. We actually cast the film before we wrote it. Patrick knew her, and her and I met in LA right before Coachella under the guise of maybe her being in the movie, and we really hit it off. We did the movie together and got really close, and after that experience she wanted me to direct her videos. 

Doug: Were both videos planned at the same time?

Grant: No, we shot another video even before “Everything is Embarrassing” that’s yet to come out, it should come out in a couple weeks. The song “Everything is Embarrassing” was leaked, or released, or somehow got on Pitchfork, and the label told me they needed a video for “Everything is Embarrassing” to shoot in 24-hours because Sky’s leaving for New York. So I thought, “Oh, God.” We’d already shot a video for “Sad Dream” earlier that month and I had already shot the video for “Lost in My Bedroom” which will come out pretty soon. I was trying to figure out what to do because there was no budget, so essentially I just took my camera and we shot some stuff of her singing the song. I just wanted to make her look beautiful and do something interesting with the short amount of time that we had. 

Doug: One of the things I really love about that video is Sky's ability to capture the audience’s attention by looking at the camera, almost making eye contact with the viewer. Was their any coaching on your end to make that work so well, or is that just Sky’s natural presence coming through? 

Grant: What I love about working with Sky, and what makes my job so easy, is that she lets me do my thing and I let her do her thing. She’s so enigmatic. She’s like a natural, I guess you can call it star. That’s one of the reasons why I cast her in IRL, she really is a star. I think she is going to do really increasable, huge things and I feel very fortunate to have worked with her. But, that’s all Sky. I wanted to capture a little bit of that really electric quality to her personality and her presence that I think she brings in her everyday life. That’s all her, I don’t take credit for that at all. 

Doug: Originally, I thought you were intentionally contrasting the locations between the two videos, one in the city and one in the country, and kind of playing with that juxtaposition. But, now hearing that “Everything is Embarrassing” was more spontaneous, it seems like that might not be the case. Was my initial read on that wrong? 

Grant: At first, it was all about trying to figure out who to cast as the love interest in “Everything is Embarrassing.” We thought it would be cool to have a love interest, and we tried to get a friend of ours who is also a musician to do it but he was leaving for tour that day. So then I just had the idea to do the video in a playground, so that’s how the playground thing happened. Then basically we just shot at the locations that we could get. We shot of the roof of Capital Records, which is her label, we shot in the subway, just random locations that we thought could be interesting that weren’t just the front yard of a house. Totally spur of the moment. 

Doug: How did the production, and crew size, compare between the two videos?

Grant: There was no crew for “Everything is Embarrassing.” It was me, the guys who works for me who you could call the AC but basically was just holding my camera bag when I was shooting, and then Sky. Basically, just me, my camera, and Sky. There was no crew, it was just us. Then “Sad Dream” had a very large crew. I worked with the DP Jason McCormick, who shot my movie. I work with him any time I can get a budget because he is really great. 

Doug: Last year Sky released an EP called As If!, and then this year she put out Ghost, which seems to have a different vibe to it and kind of represents a different direction for Sky’s career. With both of these albums coming after the career shift, were you asked to consider her new direction when conceptualizing these videos?

Grant: Not at all. I’m not going to speak of behalf of Sky, but she’s 20-years-old. When her older stuff came out she was essentially a child, she was a kid. I don’t the she had as much say in terms of the direct of her music. Where as now, she’s very much in control of who she works with. The kind of music that she’s making is very representative of who she is. I respect Sky so much as an artist and as a friend. I just want to make videos for her that do her music justice. I’m not really interested in music videos as a thing. Most of the music videos I see, I’m not really into. I’m more interested in film and other things. My approach to stuff is really just taking a song and creating a world, evoking a feeling. I’m not really into plots for music videos, I’m more about capturing a feeling, or world, the environment in which the music was made in, stuff like that. So, I was not asked to approach it any differently. Sky and I teaming up, I have a specific aesthetic and she respects that and wants me to do me thing. We talk about the idea in the beginning, and then she’s completely hands off. She has very few notes, she’s your dream collaborator. She trusts me and I trust her, we have a really great relationship, which is way we continue to make more and more videos together. 

Doug: One of my favorite things to look at on YouTube is people trying to “uncrack” the storylines behind a video, and I see that a lot on the “Sad Dream” comment section. You talk about not focusing on the plot of a video, so is there no real a backstory there?

Grant: There is definitely a backstory and a relationship between Sky and Mark Polish, who is the guy in the video and is a really amazing filmmaker. He and his brother Mike Polish are the Polish Brothers, they’re incredible filmmakers, and I was surprised that people didn’t pick up on the fact that he was in the video. There is a specific relationship, but I think leaving it vague is more interesting. I’m a firm believer in that it’s much better to watch something and have more questions than you have answers, and I think Sky is as well. I think that’s why we kept it mysterious and not so clear. 

Doug Klinger is the co-founder/content director of IMVDb and watches more music videos than anyone on earth. You can find him on twitter at @doug_klinger.