The Unhinged Brilliance of Cecily Strong (2024)

The “glamour girl that goes wild,” as Cecily Strong describes her, has become something of a calling card for the Saturday Night Live star. Whenever the newest woman to fit the bill first makes news, Strong gets flooded with pleas for her to portray her. “I’m glad my name comes up,” she tells Vanity Fair with a laugh. “I worked so hard for it.”

This was a standout season for Strong, even though she largely only appeared in the back half, having been busy filming her AppleTV+ vehicle Schmigadoon! last fall. Along with legendary mainstays like Jeanine Pirro, she introduced new sidesplitting interpretations of folks ranging from former Trump lawyer Sidney Powell to hard-right congresswoman Marjorie Taylor Greene. “It feels like this year, especially, anything that we’ve said that might be too crazy has actually worked out really well,” she says. “It’s the gift of 2020 and 2021.” Competing on her second consecutive Emmy nomination for outstanding comedy supporting actress, Strong broke down her many brilliantly unhinged creations from this past season for Vanity Fair.

Kimberly Guilfoyle

Never had the line from news headline to casting call looked clearer than when Kimberly Guilfoyle gave a very loud speech at the 2020 Republican National Convention. SNL wasn’t even back in production yet, but if Strong didn’t show up in a sketch in Guilfoyle drag, we’d have to question everything we ever knew about the internet and its power. There was just one hiccup: Strong was far away from SNL, starting filming on her musical fantasia Schmigadoon! in Canada.

“It was right in my wheelhouse,” Strong admits of watching Guilfoyle over the summer. A plan was hatched for her to cameo as the Trump adviser and former Fox host: She’d film it from the Schmigadoon! set as a Trump thought bubble for the cold open, a recreation of the first Trump-Biden debate. Alec Baldwin’s Trump puts in a “meditation tape,” which is really just a recording of the amped-up conclusion to Guilfoyle’s RNC speech. (Strong notches this up by ending the bit with a literal, extended, guttural howl.)

Executive produced by SNL leader Lorne Michaels, Schmigadoon! was just getting into production, and it was a team effort on the set to make sure Strong could sneak her way into the SNL premiere. A red dress approximating the one Guilfoyle wore was sent over from New York. The Schmigadoon! hair and makeup team put the character’s look together. Strong made quite an impression on her new collaborators. “Canada is known for being a very polite country, and I’m there, like, screaming—before I shot anything with these people!” she says. “I’m yelling, these camerapeople are just kind of standing there. That was a little bit of a shock. Worth it, though.”

Billie Moon

If Strong’s got a second signature beyond her particular brand of conservatives gone cuckoo, it’s characters with a distinctive love for singing. In her first episode back in studio, she debuted the character of Ms. Billie Moon, an “outdoor cabaret” singer paired in a kind of Barbra-Judy number with Bowen Yang’s Charlie Vig. Right away, it’s the kind of person Strong nails: charmingly over-the-top, prone to drunken slurring, and with an undeniable voice.

Strong had a very specific vision for the makeup. As she describes it: “It’s too much. She’s doing stage makeup, but it’s real life—but that’s the makeup she knows. Like, that’s how you accentuate your eyes and your cheeks.” She googled “silver, short haircuts” before sending over options to the hair department—a favorite tradition of hers—and found the character’s soul instantly. This being her first episode back in some time, she was still required to belt out a few numbers. “It always makes me the most nervous—hoping that you have a voice by 12 that night after a week of work. It’s like, oh, God, I hope it isn’t the day I crack horribly on live TV,” she says. Fortunately, it wasn’t.

Marjorie Taylor Greene

There was never much doubt that Strong would play the Georgia congresswoman, who skyrocketed in profile after various public stunts and gaffes. “It’s a real honor,” Strong says wryly of the typecasting.

She does basic research as she begins preparing for an impression. “I watch enough to try to get a voice down and the way someone speaks and their mannerisms and their face, but not too much,” she says. She and cowriter Bryan Tucker (her frequent collaborator on characters like Greene) also had to be careful not to go too overboard—in the case of a person like this, the words they actually say are likely plenty out-there on their own: “The things she’d been saying were so easy to poke fun at anyway.”

So they instead opted for subtler, weirder gestures: In the multiple sketches in which she’s introduced, Strong as Greene begins by nonchalantly pulling out a gun, nodding to her adamant anti-gun-control positions. And Greene’s SNL trademark is, for no particular reason, sneezing as exorcism—an idea Strong came up with on the fly, “not really thinking,” when brainstorming the character with Tucker. As he told her after she brought up the idea, “Well, it made me laugh!”

Greene also provides a good example of the kind of line Strong draws when deciding on whether to impersonate someone she so intensely disagrees with. “If I can’t find something fun enough, then it just feels icky; if there’s not a way to turn someone into my own thing and a clown character, I don’t necessarily want to push them as a public figure,” she says. “But when it’s, like, the idea of attacking the LGBTQ community, I can make fun of that all day because it’s just insane to me to spend your time doing that.”

Sidney Powell

The attorney who joined Trump’s legal team in the effort to overturn the results of the 2020 presidential election presented one familiar problem for Strong: name recognition. “We actually wrote her and brought it to the table for the first show I came back on [in December], and it [felt] too crazy. I didn’t know if anybody knows who she is,” Strong recalls. Then another unknown caricature emerged in Mellissa Carone, “the Michigan wild woman” who was a pro-Trump “witness” of election fraud. So she and Tucker decided to focus on her (and did they ever!) while putting Powell on the back burner.

The opportunity to debut the character arrived later, though, when Dominion Voting Systems decided to take legal action against Powell and company. On Weekend Update Strong slid on to the desk “dressed like Fred Flintstone’s mother-in-law,” with a devilish cheshire-like grin and a stiff double chin. As to how she contorted that perfectly imperfect expression? “A lot of watching videos,” Strong says.

Gemma

One of Strong’s more beloved recurring characters, the aspiring British singer Gemma, hadn’t been on for almost four years before she returned for the season’s penultimate episode, hosted by her Schmigadoon! costar Keegan-Michael Key. “I was excited he was coming and I was like, ‘No pressure because I don’t assume that you’ve seen everything I’ve done, but if there’s anything at all that seems fun to you’—and he said Gemma!”

She wanted to take the character in a different direction for her return, letting her do a gloriously full performance this time. Originally inspired by one of Strong’s favorite reality shows, The Only Way Is Essex, Gemma’s thick accent only enhanced her bizarre lyrics. In this case, they went timely, handing her a ridiculously vaccine-inspired number. (Strong’s personal favorite line: “Feeling naughty because I got the antibodies.”)

Strong’s process of writing the lyrics sounds simple—“Just kind of sitting by myself, like I have been long enough”—and also, perhaps, gets at the heart of Gemma’s appeal. “I feel like we could all come up with Gemma pop songs with the amount of time we spend at home alone now,” Strong cracks.

Jeanine Pirro

“The magic of the night.” It’s what Strong keeps coming back to when describing her remarkable, character-capping performance as Judge Jeanine Pirro in this past season finale.

The Fox News host has developed into Strong’s most iconic role in the years she’s been playing her. “We were just watching clips of her ‘Man on the Street’ thing, and she kept being like [impersonates Pirro], ‘What?!’” Strong recalls. “Her reactions—it was like, wow, she’s just screaming. What fun!” Since she first brought her out, Pirro has mostly been a Weekend Update mainstay, drunker and more likely to fall out of her chair and with more wine to spill in Colin Jost’s face with each passing appearance. “It’s just asking yourself, how do we top it?” Strong says of how the character has evolved. “It’s as simple as that, honestly, in how you end up with the tub of wine.”

Ah, yes, the tub of wine. In the season finale, amid speculation that this season would be Strong’s last—still no confirmation of that—Pirro got what seemed to be a spectacular send-off in the form of a rendition of “My Way,” while soaking in a vat of grape juice (disguised as Pirro’s red of choice).

“I know it’s a good show if I’ve made the safety team a little nervous,” Strong says. Mission accomplished here. She had a backup plan—flash-dancing with the chair to “What a Feeling”—in case it couldn’t come together. She sent the creative team a picture of “a magician in a box of wine” for inspiration. “I said, well, we won’t do the weird chains and blood, but it should look like that otherwise,” Strong says. “Somehow they made it happen.” She barely rehearsed, since they didn’t acquire the tub in question until the last minute: “Saturday afternoon, I got a text like, do you want to come test out the tub? They filled it with warm water and I wore sweatpants and a T-shirt. I’m at the end of the hall at 30 Rock getting into this vat of water, going, ‘Oh, this is great, guys.’”

Yet the sketch, which shows off Strong’s incredible pipes along with the effortless Pirro-esque slurring, went off perfectly. Even the way she dunked a glass into the vat and flung wine aimlessly behind her was seamless—it landed right in Jost’s face. “I’m not much of an athlete, so I don’t know how skilled I’ll ever get,” Strong says at her practice in throwing drinks Jost’s way. “I’m used to a wine glass, though, that’s for sure.”

Strong isn’t sure if this Pirro bit can be outdone, so for now, it may indeed mark a farewell for the character. (If not, expect something “insane.”) She got a standing ovation for the performance too, but was dripping wet offstage and missed it. “I didn’t see my one standing ovation in nine years!” Strong says. “I was being dried off, wiping grape juice off of myself.” For Jeanine—and for Strong—it couldn’t have gone any other way.

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