In the summer of 2000, Sam Raimi took a team to Rockefeller Center for a kiss. On the hunt for Spider-Man shooting locations, the director had targeted the building’s rooftop gardens for a golden-hour romantic encounter between the titular superhero and Mary Jane Watson. Though MJ was originally scripted to kiss Spider-Man over his mask after tending to his chest wound, Raimi grew concerned with the web slinger’s stilted positioning and realized that bathing an intimate moment in sunset would be a logistical nightmare. “We really wouldn’t have had enough time to do the scene,” says Doug Lefler, Raimi’s second-unit director and storyboard artist. “Nobody was really happy with the compromises.”
Upon returning to their Los Angeles production office, Lefler started looking for a workaround. He found one in his past: Throughout the 1990s, the television director had frequently staged various characters falling into frame upside down, first in an episode of Hercules: The Legendary Journeys and then again in a scene from F/X: The Series. “I just liked the silhouette profile to profile,” he says. “It struck me as cool.” Copying from his own work, Lefler began storyboarding a scene in which Spider-Man lowered himself upside down into a rainy alley to meet the level of Mary Jane’s waiting lips. “It seemed like an opportunity to do something that was visually strong but belonged to this story,” Lefler says. “It was very much a Spider-Man thing to hang upside down.”
Raimi loved Lefler’s sketch—especially after producer Laura Ziskin suggested Mary Jane remove part of Spider-Man’s mask to kiss him. And though the alley wasn’t exactly Fifth Avenue’s beatific perch (which would eventually be used for a different scene), the change in location—and body position—enabled Raimi to shoot in a more controllable, backlot environment. “He latches on to things,” Lefler recalls. “If you explain it to him and you present it in a cinematic way that he can understand, he’s very tenacious about it.” With the updated boards, writer David Koepp and producer Alvin Sargent began revising the scene, spinning Spidey’s acrobatic antics and Mary Jane’s surprise attraction into the script and setting up what would become the movie’s most indelible shot.
It takes place around the midway point, after a maskless Spider-Man (Tobey Maguire) has wrangled four muggers away from Mary Jane (Kirsten Dunst) and fought them into submission. In the pouring rain, he quickly jumps around a building to avoid recognition and then reappears moments later, beside her, masked and upside down. Looking to give her “superhero stalker” a thank-you kiss, MJ gently pulls down his mask just above his nose and initiates a slow, passionate make-out session; then she lingers, pecks his chin, and re-covers the bottom of his face. As Danny Elfman’s soothing score crescendos, Spider-Man slings a web and bullets toward the roof, leaving MJ breathless in the flooded alley below.
Within the context of the story, the scene is a cathartic release for Peter Parker, a rare opportunity to embrace his dual identity and be vulnerable with the girl he loves. On a much larger scale, it’s one of the most iconic and romantic kisses in Hollywood history, a unique and asymmetrical composition of rain-soaked, interlocked lips never seen before on the big screen. Spider-Man kicked off a wave of superhero saturation, yet 20 years later the kiss remains unforgettable—a testament to the chemistry of its actors, a nostalgic reminder of the blockbuster’s sneaky romantic potential, and a recurring subject of earnest homage. “It has an emotional connection to the audience that we always strive for,” Spider-Man cinematographer Don Burgess says. “Sometimes, it becomes bigger than all of us.”
The first official kiss between Peter and Mary Jane dates back to 1975. As written by Gerry Conway in “The Amazing Spider-Man No. 143,” the pair kiss inside JFK International Airport, awakening a long-dormant romance as Peter boards a plane to Paris. About 20 issues after the death of Gwen Stacy, the heated moment began a new arc in Spider-Man’s conflicted love life. “When Gwen was eliminated from the story line, I wanted to develop this relationship with Mary Jane, and I knew that Peter first had to process his guilt and remorse and grief over the loss of Gwen,” Conway says. “It was meant to bring us to this moment where the two of them would finally have their romantic realization.”
Peter’s abrupt departure after kissing MJ would eventually become a theme in the comics, and throughout Conway’s storytelling run, the author threw “everything that we could into their path to make it an impossible situation for them to come together,” he says. Though he always made sure that Peter—not his alter ego—kissed Mary Jane, Conway knew that his protagonist’s double life would become a burden in the midst of fighting supervillains. “The frustration element is what provides the substitute for sexual gratification,” Conway says. “That kiss was to be the centerpiece of it, the fulcrum that the rest of the story would follow through on.”
Though Peter wouldn’t reveal his alter ego too early in Raimi’s trilogy, the director knew his own kiss scene would need to have a similar strength and dynamic. Raimi had always envisioned a grounded story centered on an awkward teenager, but the romantic tilt of the plot didn’t come into focus until he saw Dunst and Maguire—who at the time was sick from strep throat—perform a chemistry read together in Berlin. “Once we got them in the room together, Tobey’s pale pallor seemed to change, and he lit up, and I became very involved in their love story as I watched them do the scenes,” Raimi said in 2002. “It felt real, and I wanted to see more of it.”
In the first half of the movie, Peter repeatedly fumbles opportunities to speak to MJ, but he finds new confidence as Spider-Man. His competing identities, however, culminate in the ensuing alley scene—a “threshold moment for the character,” as Raimi once described it to Rotten Tomatoes. After Peter declines MJ’s invitation to have dinner with her, he springs into his spandex when he sees her being followed by suspicious men. A few moments later, he webs them off her, emulating a scene that Maguire had already performed in preproduction to quell Sony’s fears about his physique. “We put together a little sequence to demonstrate what Tobey would look like,” stunt coordinator Jeff Habberstad says. “We actually got to rehearse that a bunch in advance.”
To shoot the real scene, Raimi rented out a section of the Warner Bros. studio lot, giving him and Habberstad more control over the necessary rigging and rain machines. But the space also helped creatively, like when Burgess wanted to capture Maguire’s transformation from maskless fighter to upside-down wall climber without any cuts. “I had [the crew] build a trap door in the building so that the first Spider-Man could disappear behind it, and then the second Spider-Man could be lowered upside-down into frame in front of her,” Burgess says. “The execution part of it is always far more difficult than we anticipate.”
The rain provided an even bigger challenge. In order to see the drops falling, Burgess set up backlighting and requested that the special effects team enhance the sprinkler valve pressure, making sure his cameras were sufficiently waterproofed for the onslaught. “You’re in full rain gear,” he says. “It takes a lot of effort from all the departments to get it right.” Maguire had already rehearsed the sensation of being upside down in a dry environment, letting Habberstad secure and test his harness before trying it again with a hosed-down suit. “You want to have that planned out to where you don’t have him hang upside down for 10 minutes while you get things ready,” Habberstad says. “[Being] upside down gets real uncomfortable real quick.”
Before production began, Raimi gave Dunst a coffee table book filled with famous movie kisses, a bit of inspiration “that made me realize how romantic and special Sam wanted this to be,” Dunst told W Magazine. But when it was time to lock lips, the romantic air had evaporated under the 5 a.m. pelting rain. Because Maguire’s mask was bunched above his lips, water began dripping into his nose, making it nearly impossible for him to breathe. “I was gasping for breath out of the corner of Kirsten’s mouth—poor girl, I was giving her mouth to mouth rather than kissing her,” Maguire recalled. Though it didn’t take long to shoot, “he was slightly drowning because he couldn’t wipe his nose,” Raimi recalled. “It doesn’t look unpleasurable, but I think it must’ve been.”
Making matters worse, the pair had to re-create the kiss on a separate night because Maguire’s tight-fitting, wet mask had become unpeelable. The costuming department had to customize new headgear, which Habberstad remembers “was already slit around the neck and loosened up enough so that she was able to pull it down past his lips.” But thanks to deft editing and Dunst’s sleight of hand, the alterations “helped sell the idea that she actually pulled the mask down,” Raimi said. “It was a lot of technical aspects but fortunately Kirsten and Tobey are so convincing that they made that all invisible.”
Though Dunst mostly remembers “two nights of freezing in the rain,” the filmmaking team felt it had produced a magical moment. “The partial pulling back of the mask and the rain and the backlight, it was an amazing combination,” production designer Neil Spisak says. It also merged Peter’s split realities, giving him a taste of what life with MJ might be like. “That’s why her pulling down the mask makes the moment special, because his character longs to be loved by her,” Raimi said. “He wants to be accepted by her, and to remove the mask is the idea of exposing yourself.”
The effects of that decision also linger into the movie’s final scene. At the funeral for Norman Osborn, MJ plants another kiss on Peter for what she thinks is the first time. Peter denies her invitation to be together, but as he leaves, MJ puts her fingers to her mouth, recognizing his lips and realizing her best friend might also be a superhero. “I’m a sucker for the idea of that moment,” Burgess says, which borrowed from Conway’s own belief that MJ always knew Peter’s secret.
“There’s an inevitability to them,” Conways says. “[They] are so entangled with each other that it’s hard to imagine one of them without the other.”
When Joel Gallen created the MTV Movie Awards in 1992, his goal was to create an Oscars-type telecast that would cater to the channel’s younger, pop-culture-inclined demographic. Mostly, that meant incorporating new categories into the show. Amidst highlighting action sequences and villains, it didn’t take long for Gallen to determine that no category would be as popular as Best Kiss. “It’s just one of those things that everybody connects with,” he says. “That’s what people always talk about.”
Ten years later, after seeing Spider-Man debut in theaters, Gallen could already hear the chatter for next year’s show. Over the previous decade, fans had awarded all kinds of memorable kisses, from the innocent (Anna Chlumsky and Macaulay Culkin) to the goofy (Jim Carrey and Lauren Holly) to the absurd (Sarah Michelle Gellar and Selma Blair). But this one felt unique—a steamy kiss tailored to MTV’s comic-book crowd featuring attractive young stars in a critically acclaimed blockbuster that earned $821 million at the global box office. “Where else are you going to see that than in Spider-Man,” Gallen says. “Most kisses are pretty much the same, but this was a very unusual kiss, and very well captured.”
As if telegraphing its victory, Gallen loved the kiss so much he helped stage a parody of it for the 2003 show, tapping cohosts Jack Black and Gellar to spoof the scene in a prerecorded short video. Later that night, Dunst, who would also win Best Female Performance, hopped on stage to accept the Best Kiss award, thanking an absent Maguire (who was already filming Spider-Man 2), teasing her competitors, and encouraging fans to see the sequel, where “hopefully we’ll have good make-out sessions,” she joked.
Over the next year, the kiss wound up in a Weird Al song and a brief Shrek 2 montage, parodies and homages that confirmed that imitation is the highest form of flattery. But it wasn’t until 2005, when Josh Schwartz placed “the ultimate comic-book fanboy fantasy” into the rain-soaked mid-second-season finale of The O.C., that its reputation skyrocketed. Centering a story on a Southern California monsoon, the showrunner realized he could pay homage to Raimi’s romantic moment with a nerdy character like Seth (Adam Brody) at his disposal. Almost reverse-engineering the script, Schwartz determined that Seth’s love interest, Summer (Rachel Bilson), would ditch her boyfriend at the airport and race back to kiss and make up with Seth, who would be dangling from the roof in a Spider-Man mask (his only water-resistant protection) trying to fix his satellite cable. “We went to some great lengths just so we could get there,” Schwartz jokes.
Much like Maguire and Dunst, Brody and Bilson found the wet conditions and lip reversal uncomfortable and unromantic. “We were on a soundstage, and it’s pouring rain inside, and Adam’s upside down, water’s going up his nose, he can’t breathe,” Bilson told InStyle. “Trying to kiss someone upside down, and your lips are moving opposite … it’s just so awkward.” With Oasis’s “Champagne Supernova” playing, the pair still produced a look-alike performance, making “The Rainy Day Women” one of the most popular episodes of The O.C.’s four-season run. (It earned 7 million viewers when it aired.) Even Avi Arad, one of Spider-Man’s producers, called Schwartz after its airing to congratulate him on his replication. “There are moments in movie pop culture that just kind of resonate, and this was one of them,” Schwartz says. “I think it was obviously enormously successful—people really loved it.”
Unwilling to abandon the kiss completely, Raimi inserted permutations of it throughout the remainder of his own trilogy, showing its ripple effect through the central relationship. In Spider-Man 2, Mary Jane kisses her fiancé while his head tilts back on their couch, as if trying to muster the old romantic magic of her Spider-Man encounter; in the third installment, at a Spider-Man celebration rally, Peter hangs upside down in his costume and encourages Gwen Stacy to “lay one on me,” betraying his special moment with Mary Jane. “I think there was definitely a conscious desire to give it a nod,” Spisak says, “[but] I don’t think he wanted to re-create it or outdo it.”
Since Raimi’s run on the franchise ended in 2007, the kiss has continued to inspire imitations on talk shows (Dawn French and Bear Grylls attempted it in front of Dunst on The Graham Norton Show in 2014) and game shows (Chrissy Teigen dressed as Spidey and kissed her husband, John Legend, on a 2017 Spider-Man-themed episode of Lip Sync Battle). It even got another jolt of energy (and conspiracy) last November, when a version of it showed up in Taylor Swift’s “All Too Well” music video. In a brief shot throughout the 15-minute short, actors Dylan O’Brien and Sadie Sink kiss each other parallel to the floor, a reminiscent act that many sleuthing Swifties believe was another allusion to her ex-boyfriend Jake Gyllenhaal, who dated Dunst for two years beginning around the release of Spider-Man.
In #AllTooWellTheShortFilm he kisses her upside down like the Spider-Man kiss, which was a scene involving Kirsten Dunst - Jake’s earliest public long term relationship. Taylor doesn’t miss a detail. #RedTaylorsVersion— Alaina, J.D., LL.M. (@alainageri) November 13, 2021
“She sent me videos and films and I put together a document with some suggestions on framing,” Swift’s cinematographer Rina Yang said. “She knew exactly how she wanted the film to play out shot by shot.”
In the two decades since Spider-Man premiered, the upside-down kiss has remained the defining image of superhero romance. Compared to the nonexistent romance of MCU movies, Maguire and Dunst’s encounter almost looks like it belongs to a different genre. “There is kind of an asexuality and antiromanticism to the current MCU that I think is deliberate because it is a ‘family-friendly’ version of these things,” Conway theorizes. “Right now, acknowledging a sexual interest is the only thing that stands out.”
That distinction has separated Raimi’s films from Spidey’s more recent iterations. (You’d be hard-pressed to find the same electricity between Zendaya and Tom Holland, who has even joked about his desire to re-create Raimi’s scene.) It’s also given the kiss an undeniable level of clout. More than a passionate and physical act, the scene has become a strangely nostalgic expression of a time when filmmakers had more freedom to lean into their personal styles, make a love interest the primary catalyst of the plot, and suggest that superheroes could be sexual creatures. “I think you have to go back to Sam wanting it to be grounded with human beings and what they’re capable of doing,” Burgess says. “If I look back on my career, the movies that stay with you are the ones that have a real story to tell.”
According to Marcel Danesi, a professor emeritus at the University of Toronto and author of The History of the Kiss: The Birth of Popular Culture, the nature of the upside-down kiss is striking in the setup itself. Based on Peter and Mary Jane’s flipped greeting, they’re no longer restricted to traditional positioning and coding, similar to how modern cowboy Westerns swapped black and white hat colors to confuse the movie’s good and evil characters. “When you reverse the bodies, there’s no more symmetry, no one on top or on the bottom, no power imbalance,” Danesi says. “The lips are the focus and the center of gravity. Everything else dissipates.”
In the same vein, the egalitarian nature of the upside-down kiss exemplifies its original purpose of bringing “two bodies together, not in conflict but in union,” Danesi says. Of course, the rain adds another literal element to the scene, evoking some of Hollywood’s other iconic kisses—the passionate ending of Breakfast at Tiffany’s or the wave-crashing wetness of From Here to Eternity. “It just adds more drama and flair to something that might be boring,” says Gallen, also noting the boat scene from MTV’s 2005 Best Kiss winner, The Notebook. “Who wants to see a kiss in broad daylight? It should be nighttime, it should be raining, lightning. Who knows? It just makes it look better and more intense on screen, and sometimes makes it even sexier because these people don’t care that it’s pouring rain.”
Perhaps most importantly, the shot’s simple, static framing reflects the slow and deliberate nature of Mary Jane’s advance, giving the audience a beat to appreciate a tender moment in an otherwise action-heavy movie. “I think the profile is certainly the image I remember,” says Burgess, recalling his mental checklist: “Does she have her left hand on his face? Does she just have the right hand so we can see his face better? Do we rotate them around this way? How do we make sure we see the emotion of the characters when half the face is covered with a mask? All those things on the day of shooting you have to figure out.”
“It was just the right idea for the right moment,” says Lefler, joking that the scene’s popularity made it impossible “to stage anything that way [again].” But while most filmmakers will contend they can never predict what shot, line, or scene will become iconic, Lefler recalls the opposite occurred before shooting had even begun. “I have this memory of being in a meeting with Sam and Laura looking at the boards, and her saying that this was going to be the moment everybody remembered,” Lefler says. “And she was right.”