Jennifer Coolidge Will See You Now

How America’s most fabulous character actor made Hollywood come to her.

by Anna Peele
Jennifer Coolidge laughing during a phone call with a glass of champagne

Jennifer Coolidge has received a disturbing call. Coolidge picks up the phone several seconds into our interview and learns the luggage Delta had lost and then found has been deposited outside of the gate protecting her house in the Hollywood Hills. “They can't put it by the door!” Coolidge says, standing and spreading her non-phone hand in a splay of frustration. “I'm in a bad neighborhood!”

Coolidge’s glottal purr rises to a peal. “It's $6,000 worth of clothing in that bag!” she says. “I don't know how to handle this!”

The woman on the phone says she called Coolidge three times with no response. “It doesn't matter!” Coolidge cries. Her hand windmills as she searches for a metaphor that illustrates the absurdity of this luggage-abandoning policy. “I could be a surgeon and I could be operating on someone right now! It doesn't mean you can go drop a suitcase outside my door!”

Coolidge hangs up and calls someone named Mike, who had long ago rescued the bag; didn’t she get his text?

Exhausted by the ordeal, Coolidge tips sideways onto the photo studio sofa like it’s a fainting couch. “I thought you handled that really well,” I say, touching her bicep. It is the softest skin I’ve ever felt. “You saw me lose it,” Coolidge says. “I’m sorry.” Still, she had a right to be upset. What if there had been something invaluable in her bag, she points out, like her mother’s ashes? Or what if she really were a surgeon, I reply, and her lost luggage contained a heart she needed to transplant?

Coolidge squinches her eyes and tumesces her lips. “Except… wouldn’t my heart be in my carry-on?” she says.

Vex coat, De Beers necklace, Miscreants gloves, Casadei shoes

This episode has all the shambolic glamor of a Jennifer Coolidge character: a woman haplessly trying to get the thing she needs, only to have her drama deflated with the prick of deadpan truth. As her friend and the creator of her new HBO show, The White Lotus, Mike White, says, “You’ll be with her, and she'll be searching through her purse and, like, trying to find her phone. You're interacting with somebody at the coffee shop, and you think she’s totally lost in her own thing. And then as the person you're talking to walks away, she's totally got a take on that person and does an impression of them. She uses that obliviousness as a way to disarm people, but she doesn't miss a beat.”

White wrote The White Lotus, a profoundly funny limited series about spoiled yet pitiful white people at the hellmouth of entitlement, a tropical resort, so he would have an opportunity to work with Coolidge. (It is also perhaps the first show that illustrates how annoying white privilege is without being annoying itself.) Coolidge plays a wealthy, emotionally adrift woman nominally mourning her mother’s death — she literally does have her mom’s ashes in her luggage — but more focused on searching for answers and love and a good massage. The character, in what might be the greatest performance in a career that includes the most memorable parts in Best in Show, American Pie, and Legally Blonde, imprints as a disciple on a Black spa manager played by Natasha Rothwell. Coolidge’s character blithely dangles money and opportunities in front of Rothwell, hoping to capture in some more permanent form the cared-for feeling Rothwell provides. "Was that," Coolidge asks fretfully, "the being upset about the bags thing... a White Lotus moment?"

Of course it was. But there’s more to it than that. Coolidge implores me: “Gosh, can't you rewrite the story? So that I just don't sound like this fancy lady yelling at the young lady?” Even the cost of the clothing in question is “not typical of anything that ever happens in my life, because that's not my story,” she says. “It’s so much more pathetic than this.”

Coolidge had purchased the pieces in New Orleans, where she mostly lives, because she was nervous that she’d show up to her Bustle shoot and wouldn’t be able to fit into any of the clothes the stylist had pulled. She knew she wasn’t the easiest-going model to begin with because she doesn’t wear animal products. So Coolidge had gone to a vintage shop with the idea that she’d bring these backup clothes, and then the saleswoman at the store had been so helpful and had stayed past closing time, so when she told Coolidge the eye-popping total, Coolidge thought, “Uh-oh.” And then she thought, “Oh my God, this girl who I asked to stay longer, am I now going to tell her that I'm not getting all of this stuff?” And then she thought, “Fuck, what am I going to do with all this stuff after?” It was a mess. So Coolidge bought the outfits that wouldn’t arrive in time for the shoot, telling herself that she would resell the clothes to a consignment shop later. But, Coolidge says, wincing, “I don't know if I could've done that. I'm not good at selling things. My gifts are limited.”

Vex coat, Dead Lotus corset, De Beers necklace, Miscreants gloves, Casadei shoes
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Coolidge was born to WASPs in Norwell, Massachusetts. After graduating from Harvard, her father sailed around Maine with a piano, tuning instruments along the coast before becoming a plastics manufacturer, marrying Coolidge’s mother, and raising four children. The couple “were always coming to people’s rescue,” Coolidge says, to the extent that they became local marks. “Jenny,” Coolidge says, clenching into an imitation of her dad’s Boston Brahmin, “Ken can't get a job because he doesn't have a vehicle to get around to the job interviews. So we got Ken a car!” A month later, Coolidge says her father came back to her with an update: “You're not going to believe what happened, Jenny, but someone stole Ken's car!” Then: “You know, Jenny, Ken wants to go to a job interview, but he doesn't have a suit. So your mother and I got him a suit." And a week later: "Jenny, you're not going to believe this: Someone stole Ken's suit out of his car!"

Coolidge shares this impulse toward borderline self-destructive generosity. Her friend Chase Winton, whom Coolidge met at the improv and sketch comedy training program The Groundlings Theatre & School after she moved from New York to Los Angeles in the ’90s says Coolidge is constantly helping others, giving money to those in bad positions, and rescuing animals. Coolidge once hired an assistant who was going through a rough time. During the assistant’s employment, Coolidge took a project that filmed in Encino with a 4 a.m. call time. The assistant couldn’t drive, so every day, Coolidge would pick the woman up at home and drive them both to the Valley. The assistant sat in the passenger seat, pulled her baseball cap down, and said, “Wake me up when we get there.” Not even inanimate objects are exempt from Coolidge’s empathy. Winton remembers going to Coolidge’s house and seeing 12 wooden pigs sitting on 12 wooden chairs. While one seated pig might have been sufficient for most, Coolidge couldn’t bear to break up the set.

Gucci dress and gloves, Chopard ring

Her home in New Orleans is another object of Coolidge’s nurturing. She purchased the house in the Lower Garden District, along with a building in the French Quarter that she later sold, right before Hurricane Katrina and has been renovating it since, one room at a time. “It's not that I take such pride that it's a mansion,” Coolidge says, taking a sip of Burgundy. (She drinks French reds because, White says, “for some reason she thinks of French reds as the only ones that don't give her a hangover.”) “It's just an old, majestic home. I just wanted to restore it, and then my job will be done.” Coolidge explains, “I'm keeping it ancient inside. There’s so few great places where the inside is intact and people haven't done modern stuff to the interiors. I don't want to sell it to anybody because they'll put, like, a jacuzzi in there. And I just want to save it, and then pass it on to a [historical] society that protects it.”

“It’s her money pit,” White says. “It feels like it's her Sagrada Familia — that church in Barcelona that’s famously never been finished, over hundreds of hundreds of years.”

While White sees it as an ongoing creative endeavor, Coolidge says the reason she can’t finish is financial. There have been mainstream roles she’s taken that seem like they’d have been more lucrative than they actually were. Once, capitalizing on Coolidge’s indelible Legally Blonde 2 line, “You look like the Fourth of July! Makes me want a hot dog real bad,” Hebrew National offered her a spokesperson contract. They demurred when she said it would have to be a vegan wiener. Coolidge’s only attempt at producing, with ex-boyfriend Banks McClintock, yielded one never-made sitcom that generated $75,000, split three ways. “I'm thinking, how can I have some miracle idea?” Coolidge says. “Just some idea no one has ever thought of that is going to generate massive amounts of money?” Coolidge collected all the scratchers used as props in this photo shoot, passed half of them out to the crew, and diligently mined for a fortune that wouldn’t reveal itself from the foil.

Gucci dress and gloves
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Also on Coolidge’s list of so-far-unfulfilled desires is a partner. “I just want a really nice person,” she says. “I've had the relationships where it's 5 o'clock in the afternoon and you realize you've had like 15 fights with the person since you got up. I don't want to do those ones where the guy's behavior never adds up. Where you feel like you're a detective and like everything they do is sort of some weird step where you're like, ‘I'm going to get to the bottom of this.’ I just want someone who is just an incredibly well-adjusted person but a lot of fun and gives a shit about humanity.” Coolidge looks out the window, illuminating a silhouette that looks like it should be rendered in marble as she picks the final quality of her imagined mate: “Easy and breezy, and if I get too upset about something, they're like, ‘It's not a big deal.’” Then she thinks about her luggage, and how irritating it would be to have a partner who said that wasn’t a big deal. She reconsiders her previous assessment. “You want the guy that's like, ‘That's fucked up,’” Coolidge proclaims. “I don't want the guy that goes, ‘Don't worry about it, Jennifer.’”

“I'm thinking, how can I have some miracle idea?” Coolidge says. “Just some idea no one has ever thought of that is going to generate massive amounts of money?”

But chasing dreams is arduous. “What’s not tiring?” Coolidge, an insomniac of 15 years, asks. Perhaps the greatest hallmark of any Coolidge character is how actively they want things and how passively they pursue them. In a career-establishing role as Stifler’s mom in American Pie, Coolidge says, “I got some scotch. … Aged 18 years. The way I like it." But she leans back with a cigarette and lets the other 18-year-old come to her. Coolidge sees the character as a MILF, not a cougar, because she’s the pursued, not the pursuer; “Cougar sounds like some old cat that’s going to eat the other one,” she says. Coolidge famously pretended to be twins so she could date a pair of friends on vacation, but she also tells me she could never ask a man out. “I just don't want to put myself on the line like that,” she says.

Gucci dress and gloves, Chopard ring

It makes you understand how it was possible that it took two decades for someone as beautiful and talented as Coolidge to start regularly booking parts. She is a people pleaser, but one without the energy or ability to change herself to please those who don’t naturally find Coolidge pleasing. In Coolidge’s first television role, one of a paucity of acting jobs she got while waiting tables and attempting and aborting a career as a makeup artist, she played a masseuse on Seinfeld who dates Jerry and refuses to give him a massage. She was 32 when she got the job. “I wasn't acting,” Coolidge says of the part, which is a little stiff even for a one-episode Seinfeld girlfriend. “I don't know what I was doing. I was so nervous I don't know what was coming out of my mouth.” Nonetheless, it was immensely important to Coolidge, whose mother was dying of cancer. “Thank God she saw that one acting job before her life ended,” Coolidge says. “She was so worried that I was never going to have even a tiny success — like anything. So it was cool for her to sort of maybe think that maybe I had a shot.”

But Jennifer Coolidge only became the Jennifer Coolidge we know when people started letting her act like the Jennifer Coolidge she really was. “To not have any sort of restrictions is when I do the best,” Coolidge says. “You never know how she's going to approach a scene or how wild she's going to go,” says White. “Sometimes when I’m writing, that kind of person can give me anxiety. But she's pretty unmatched as far as just somebody who can bring a new take on a line or a scene and make it hers.” Rather than asking her to be the person they want, her friend Winton says, people now realize, “I want whatever she’s got.”

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For Mike White’s 40th birthday, Coolidge hired a man in a gorilla costume to come to his party. The gentleman burst in, disrupted the proceedings with an ape-like dance, and loped off. Coolidge pouted when he left. “I thought he was going to strip!” she said.

Winton remembers being late to a bridal shower because Coolidge had seen something at a thrift shop she wanted to buy for the bride. Winton suggested they stop at a department store and get a gift card, but Coolidge was adamant: They needed to purchase a hundred-pound bronze statue of an erect penis, and then they needed to find the appropriate wrapping paper for it.

Talking to Coolidge’s friends, one is reminded that there is a cost to effortfully molding yourself to others’ expectations, and Coolidge hasn’t had to pay it. Yeah, she could be richer or more famous. But she has the fortune of living authentically, and we have the fortune of glimpsing a life executed as artfully, truthfully, and freakily as Coolidge’s actual performances. “She’s like really good poetry,” Winton says. “She's always surprising, doesn't give you what you expect, and doesn't go for the easy answers. She is funny and heartbreaking and really human and honest and vulnerable.”

“Jennifer is like some kind of female Don Quixote,” White says. “She is trying to chase the perfect [thing]. And something always happens [to thwart that], even with all her best intentions. But in the process, she creates really cool stuff.”

A few days after the interview, I get an email. Coolidge is fretting again. Was I happy with her? she wanted to know. Did she say anything weird? Of course, is the answer to both questions. She was perfect.

Top Image Credits: Alexandre Vauthier dress courtesy of CLOAK, Apparis jacket, Lillian Shalom ring, Tamara Mellon shoes

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Photographer: Ryan Pfluger

Stylist: Tiffany Reid

Hair: Andy Lecompte

Makeup: Beau Nelson

Manicure: Sojin Oh

Set Designer: Robert Ziemer

Bookings: Special Projects

Videographer: Sam Miron