How Promising Young Woman Turns Your Favorite Aughts Nice Guys Into Bad Men

Emerald Fennell is devious. Brilliant, but also devious. That’s the only way to describe what she’s pulled off in her directorial debut, Promising Young Woman. The film follows Carey Mulligan as Cassie, a wayward thirty-year old woman whose only driving force is the sting she runs on shitty men: pretending to be drunk at bars, letting a guy “escort” her to his home, then calling him on his predatory behavior when it becomes clear he’s banking on her being incapacitated. These are random encounters, but soon she organizes an attack on the four people involved in the incident that set her on this path: the rape and subsequent suicide of her friend Nina.

The men who play Cassie’s would be date-rapists -- Adam Brody, Sam Richardson, Christopher Mintz-Plasse-- aren’t just familiar faces: Most of them have played at least one important role as a nice, trustworthy, good guy. Essentially, Fennell has plucked the objects of Tumblr obsessions from fondly remembered aughts films and shows like The O.C., Superbad, and Veronica Mars, making for a special gut punch when their characters behave in vile ways here.

“If you're going to make a movie about good people doing bad things, [you want people that] you instantly trust. We like them. Sam Richardson, Adam Brody, these are people that we all feel fondly towards and are totally crushable,” Fennell explains. “It helps to make the audience complicit a little bit, too, because this is a movie about people's allegiances and how complicated things get when it happens in a friendship group… it happens to a girl who maybe is a party animal, and the guy involved is maybe a really nice guy. That's where the conversation gets complicated. I wasn't interested in making a movie about venomous men and innocent victims. It was about real people who ... perhaps participated in something that certainly, when I was growing up, was just very normal.”

It feels like a special twisted love-letter to the aughts to have Seth Cohen and every other Mr. Right from the teen dramas of that era now playing the same creeps they used to protect women from. (The nostalgia in Promising Young Woman extends to the soundtrack, which includes a song only millennials remember fondly: Paris Hilton’s “Stars Are Blind.” Fennell: “I had to think, ‘What's the song that if a guy knew every single word to it, I'd fall in love with him?’”) To pull it off, Fennell kept things close to the vest—each actor she met with was unaware of her plan until the full cast list was released. “I think a bunch of actors took a lot of meetings with her and in mine, we just talked about our dating life and how we met our significant others,” says Christopher Mintz-Plasse, who shows up as an early mark of Cassie’s. GQ talked to Fennell, Mintz-Plasse, Brody and Max Greenfield about weaponizing associations with beloved characters. (Spoilers for the film follow.)

Christopher Mintz-Plasse, best known for playing McLovin in Superbad

“There's no behavior in this movie we didn't laugh about in movies from the nineties through the twenty-tens,” Fennell says. “It was just hooking up with people who were drunk, getting girls drunk at parties, filling up girls' drinks on dates. It was a gag for so long. So it's interesting now looking back on it, and people have reframed it completely and said, ‘Oh, no, no. This is terrible. People would never behave like that.’ I was like, ‘I'm sorry, did you live through 2008 or '98 or any of those times?’"

On which note, Mintz-Plasse is quick to defend McLovin. “I haven't watched Superbad lately so I don't know if there's any misogyny in there. But I do know McLovin's sex scene is very safe. She's the one that grabs him and they have consensual sex. So, we will not be canceling McLovin today,” he laughs.

Still, Mintz-Plasse didn’t have to dig deep to find inspiration for Neil, the type of novel-writing dweeb who thinks he has the best taste in the room. “I know a lot of those dudes, that guy runs in a lot of my circles,” he admits. McLovin may be off the hook, but the film still inspired Mintz-Plasse to do some soul-searching. “For people like myself, who is now in a relationship, it makes me look back on when I was single,” he says. “And I'm sure there's guys who are single that are going to see this movie that it's going to completely change the way they treat people when they go out. It's rare when a movie can make men and women have a conversation like this and actually change their actions.”

Adam Brody, best known for playing Seth in The OC

Fennell really throws the gauntlet down when Seth Cohen, Patron Saint of Simps and Cool Geeks, reveals himself to actually be just as sleazy as the next guy. “It's probably very unsettling,” says Brody, “It throws you for a loop right off the bat and sets the tone of unexpected for the rest of it.” That’s because at first blush it appears as if he’s really just playing a facsimile of Seth Cohen. There he is, meekly but affirmatively doing the right thing, shepherding a woman home and chastising his objectifying peers. (In a less emotionally devastating movie, this might’ve been a meet-cute.) And then the noble Uber ride home takes a dark turn, Brody’s Jerry changes the destination to his place, and your heart sinks. “That's what's so disgusting,” Brody laughs. “He thinks he's being chivalrous. He could have just left her, but he's rescuing her. And that lack of self-awareness and that self-delusion is really interesting. It's more commonplace than we care to admit—or are finally starting to admit.”

For Brody, the point of his role isn’t so much casting against type but more about “using our boyishness, friendliness or seeming innocence to get you as an audience to let their guard down and take a much more pedestrian look at assault.” Fennell says “there's a certain type of funny guy, who's maybe not traditionally handsome, but still [is] this underdog,” she explains. “Even Adam Brody, who's one of the best handsome men in the world, he often plays some underdog character. I think those nice guys maybe got away with a lot more than the jocks because I think they felt they were owed something.”

This type of role is rare enough for Brody that he called the experience “freeing.” “It's very fun to not have to worry one little bit about getting an audience to like you,” Brody admits. “And in fact, finding little places to be especially awful, you can highlight that. It’s like leaning into your opposite instincts.”

Max Greenfield, best known for playing Schmidt in New Girl

By the time Max Greenfield enters the picture, Fennell’s game has become fully apparent. When Cassie saunters up to a bachelor party and an orchestral riff of “Toxic” swells, we’ve seen everyone from Seth Cohen to even Tami Taylor at their lowest. The question then becomes, just how high on the nostalgic faves list will Emerald go for her Final Boss? Then Cassie knocks… and it’s none other than Schmidt on the other side of the door. (Point of order: His New Girl role is clearly Greenfield’s most notable, but his stint on Veronica Mars qualifies him even more. A refresher: he was Leo, the charming, uncomplicated junior officer who gets jilted because emotional availability is boring TV.)

When we spoke, Greenfield still hadn’t seen the finished film, so when a friend called to tell him she loved it, he had to ask: “Do I come off as the worst guy in the movie?” He assured her he wasn’t looking for a performance review, he recalls, laughing. “It's important that [Joe] is the worst in the whole movie, because he needs to be in order to close it out. They enter the movie after the lead is dead. So in order to carry those [last ten minutes], he needs to be especially bad.” (Greenfield mostly interacts with Cassie’s lifeless body, but he still adds, “There was a moment during our scene where I looked at [Carey] and thought, ‘she’s a better actor than me even dead under a pillow.’”)

Greenfield went from "’I don't want to do it. This is terrible’” to “I don't know what this movie is going to be, but I want to be a part of it,” after just one phone call with Fennell. “Tone is everything,” he says. “If you can keep your tone consistent and, in the best case scenario, really excite people with a tone that they haven't seen before, you're going to be really successful. And what's so exciting about this is, it's the tone of a new filmmaker.” “I think we're so used to seeing very, very, very serious topics dealt with in a very austere, serious, didactic way,” Fennell says. “When the women that I know discuss things and across the board, across the board of experiences, they're usually at their funniest and at their most vicious when they're talking about when they're in pain or talking about something.”

Much like his fellow cast members, Greenfield gushes over Fennell and the way she inspired them to trust in and surrender to her vision. “It's not dissimilar to when Phoebe Waller-Bridge came out with Fleabag. When you have a new filmmaker that puts a piece of art like this out, and creates their own tone, that is I think, what we all are looking for. I don't think we really know what we want until somebody shows it to us.”

Originally Appeared on GQ