Sabrina Carpenter's Beau Barry Keoghan Stars in New Music Video

“Please! Please! Please! Play Espresso!” Read a sign in the crowd at Sabrina Carpenter’s Coachella set earlier this year. The singer had just released the now inescapable hit the night prior. Little did we know, the sign was a sneaky little Easter egg for “Please Please Please”, the lead single for Carpenter’s recently announced album Short n’ Sweet, out 23 August. Carpenter’s new era is kicking off with a music video co-starring none other than her biggest hype man, the Academy Award-nominated actor Barry Keoghan.

“I’m feeling like I will never pay for another coffee again, and I’m so grateful and excited for people to hear the whole record. It’s so close to me!” wrote Carpenter over email about entering her new era post the success of “Espresso”. In the video, Carpenter wears everything from Alaïa and Dilara Findikoglu to Alexandre Vauthier Couture and custom Coach (“I always like to heighten fashion and storyline in my videos, it’s playtime for me”) while fabulously and – quite seductively – pleading to her mischievous lover to not embarrass her any longer. “Heartbreak is one thing, my ego’s another/I beg you don’t embarrass me, motherfucker,” she sings. One has to wonder, who could this song be about?

For those well-versed in the Sabrina Carpenter universe, the singer gets arrested at the end of her “Espresso” music video. “I ended the last video getting arrested, so naturally I thought it would be satisfying to start the ‘Please Please Please’ video in jail,” she wrote. “I liked the idea of falling in love with a convict and being shocked and embarrassed every time he commits crimes. I was sooo lucky to get Barry Keoghan in the video ’cause he is just magic on screen.” There’s no arguing with that.

To celebrate Carpenter’s new single and the announcement of her sixth album, the video’s director and Vogue contributor, Bardia Zeinali, and Carpenter’s stylist, Ron Hartleben, joined Vogue for a short and sweet chat about the making of “Please Please Please”.

In an Alexandre Vauthier Couture coat. Sarah Carpenter

Vogue: What was top of mind when you started putting the video together?

Ron Hartleben: Because Bardia and I have been friends for a long time and have always wanted to work together, I knew it was going to be very cinematic. I was looking to make each outfit a standalone statement on its own. Sabrina always likes to have a lot of outfit changes, and with “Espresso” we could only do so much in terms of fashion as it was on a beach. We’ve also been working together for two years now, and she’s totally more mature than when we did our first video together [“because I liked a boy”]. She’s come more into her womanhood and is even more confident now; she believes in what she has to offer the world and her artistry, so I wanted to elevate the fashion in the same way.

Bardia Zeinali: I had been wanting to do something with Ronnie forever and I love that it was this. [Sabrina’s team] knew that they wanted to have a bit of that kind of wink and sense of humour that she’s known for now, but they still wanted something – and I hate to use the word edgy – a little bit darker to contrast the sweetness of the song. What she says in the song is very beautiful and sweet, and at face value it has this very kind of airy, almost doll-like feeling. But then she says “motherfucker” and there’s this aggression and a toughness, and that’s something I wanted to explore. The first treatment I wrote ended with the dictate and a kiss on the lips, and it serendipitously tied to the album cover. It was fate, in a way.

Speaking of cinematic, I’m curious: how do you go about building this character for Sabrina with clothes and visuals?

RH: Bardia and I walked through the storyboard, and from what I could understand he was creating this character that seemed very femme and sweet but was actually the one in charge. That sense of dominance was important, and helped lend itself to the fashion. She’s the boss, so she would wear something as va va boom or dramatic as an Alaïa hooded dress. She has the confidence to wear it and is unafraid to be a standout.

BZ: One thing that came up regarding fashion was this idea of the lover having one look throughout and not changing to reflect his character’s lack of evolution, but then her constantly changing and looking different and playing these different roles. I wanted every time we saw her with him in a new scene to be a different version of herself. She’s changing, he’s not, but she’s staying regardless. That idea of sticking by someone and hoping for them to change even when they don’t was important. I also wanted her character to have a hyper fixation – something in her wardrobe she’s fixated on the same way she is about this guy. Ronnie landed on these thigh high stockings, which I’m obsessed with. She wears them basically in every scene. A nod to how she has her things and always goes back to them.

The Frankie Shop shirt, Alexander Wang skirt. Sarah Carpenter

Were there any references for you when approaching the video?

BZ: I think more than film references, I was looking at historically and famously chaotic couples. Pamela [Anderson] and Tommy Lee, Sid and Nancy, Madonna and Dennis Rodman, and then in film Natural Born Killers and a bit of Thelma & Louise. These stories about two people who are on the run or on the road, the dynamic shifts in which one person becomes more submissive and the other more dominant, where the accomplice becomes the person in control and in power, which is what happens in the video. She’s getting dragged into these chaotic situations and in the end there’s a final moment, this last straw, where she takes control.

There’s also the J Lo and Ben [Affleck] reference of My Love Don’t Cost a Thing, of them getting filmed together for such an iconic moment in pop culture. It was less about referencing and more about capturing the spirit. There’s some Madonna in there maybe, but it’s really not that.

RH: Bardia also mentioned this Quentin Tarantino sentiment when we first started talking, and that made the wheels start turning for me. There’s not a fur coat moment in a Tarantino film, but you have Uma Thurman in the yellow jumpsuit [in Kill Bill], an iconic wardrobe that is very specific and directional.

Tarantino makes a lot of sense because it has that dark undertone and this perverse sense of humour, which I think Sabrina has too.

RH: Right, Go-Go in Kill Bill, it’s very much in that world.

In Alaïa. Sarah Carpenter

There’s something meta, I’m sure, about having Sabrina and Barry play a couple in the video. I’d love to hear about that dynamic of them playing off each other but still playing characters.

RH: It’s super weird and very meta. They’re essentially playing themselves in this really elevated and theatrical way that is not themselves at all. There were moments where we’d try something and Sabrina would go, I don’t think she’d wear this. And I’d be like well, would you? With Barry, his wardrobe was very much his idea. I had the thought of doing this very Reservoir Dogs callback and have him in a suit that gets dishevelled throughout the video, but it ended up being a lot more like this Irish mob movie kind of thing, which was all him. He did mention Ray Liotta off duty in Goodfellas. Barry was super committed, and it was great to have him be so into it. With Sabrina the reference tends to be this Bridgette Bardot perfection, but here it was more Michelle Pfeiffer in Scarface. Still beautiful, still major, but there’s more darkness there.

BZ: For context, too, this was also a one-day shoot. It was very challenging and we had a lot to accomplish. It was a blessing to have Barry as the co-star because you get this level of genuine investment that happens because he really cares. He stayed the 16 hours and came the day before to do a blocking rehearsal for the fight with the stunt coordinator. The amount of energy and effort he put in while also being conscious of being out of the way or it not being about him, it was great. It’s hard to cast people in general, but to get them that dedicated is unique.

I also think that there’s this sweetness and roughness to him that’s different from Sabrina but in the same spirit. He’s so nice and kind and so adorable, and so charming, which is so important in the video. You have to believe and understand why this person is falling for the chaos over and over again.

Did you feel any pressure going into this knowing the amount of eyes it would have on it after “Espresso”?

RH: I love having that big of an audience and making a splash. I definitely get in my head sometimes, but I think mostly it’s just fuel to make it great, and for her too. I think she would say that it hasn’t happened overnight. “Feather” was a turning point, and I think the visuals and the controversy with the narrative helped make the song such a hit. It all added up to this inherently Sabrina world. You know that response to an interview that was “Jesus was a carpenter”? That’s who Sabrina Carpenter is. That exchange. It’s the double entendre and that tongue-in-cheek. It’s exciting for people to get it and be invested in it and enjoy it.

BZ: I think it changed over time as the video evolved. I think at first it was really like okay, there is this big moment and we need to follow up and come out even stronger than “Espresso”. But once we eventually landed on Barry, it felt like a thing and the weight of it changed. Now there was this responsibility because they’re a couple and they’re being filmed together for the first time in this kind of really big way. I had just shot them separately for the Met Gala, and they were respecting each other’s boundaries then, so that responsibility of doing them both justice and making them both look amazing and making sure that people understand that this is fiction while keeping it light and lovely became the priority.

Carpenter in custom Coach. Sarah Carpenter

Ron, I’m curious about what you’re looking forward to doing with Sabrina in this new era. It feels like “Espresso” and the viral “Nonsense” outros have really helped her come into this very fun and playful, yet more mature public persona.

RH: Yeah, I think you put it so perfectly. Her lyrics have matured, and her playfulness has matured in this much more explicit way. She’s always been tongue in cheek, but before it used to be an oops, did I say that? Kind of thing, versus now it’s oops, I said that and meant it. The fashion reflects that too. It was a bit more theatrical and girly earlier on, and now she wants to go for it. What’s next is just continuing to mature and elevate the fashion and go into this more intense direction and explore her complexities. The Dilara look is a good example. It’s something that Sabrina would’ve maybe thought about wearing two years ago, but now she has the power and confidence to pull it off. With Sabrina there’s always a lot of narrative, and there’s these undertones to what she’s wearing or saying that are really fun to explore. There’s a lot of nuance.