Cecily Strong of ‘SNL’ via Chicago has launched ‘Schmigadoon’ and written a memoir — but she’s still figuring it all out

During the season finale of “Saturday Night Live” in May, Cecily Strong climbed into a large clear cube marked “boxed wine” and belted Frank Sinatra’s “My Way,” lowering herself triumphantly into a pool of red wine as the song crescendoed. She was playing Fox News’ Judge Jeanine Pirro, a frequent highlight of “Weekend Update,” sloshing her booze onto co-anchor Colin Jost while rat-a-tat-tating litanies of racist scorn. Strong, for nine seasons, had been “SNL’s” dependable, renewable energy source, the go-to cast member for all matters of outsized confidence masking outsized obliviousness. Think of her Melania Trump. Think of her Girl You Wished You Hadn’t Started a Conversation With. Still, a showstopper in a vat of vino — that played like somebody saying goodbye.

As bittersweet as it was funny.

She was leaving “SNL,” right?

That night, there were hints of Pete Davidson (7 seasons), Kate McKinnon (9 seasons) and Kenan Thompson (18 seasons) leaving, too. But by midsummer, we didn’t know the status of any of them. I asked Strong myself if she was leaving, and the Oak Park native was still weighing her pros and cons, saying “SNL” is not the “SNL” of decades ago, that “SNL” can be a headquarters while you try other stuff, etc. She sounded sincerely conflicted. It would be a loss if she left: As large as “SNL” casts have grown (it’s up to 20 now), Strong has the designated hitter role in the lineup once held by Phil Hartman, Bill Hader, Dan Aykroyd — not the biggest star on the show, but arguably the most valuable.

On the other hand, she would go out on a high point: She was just nominated for an Emmy for “SNL,” she’s co-starring and coproducing “Schmigadoon!” a new series for Apple TV+ about a backpacking couple (played by Strong and Keegan-Michael Key) trapped in a musical. Most interestingly, she just wrote her first book, “This Will All Be Over Soon,” a memoir, decidedly less funny, about a cousin’s death, a relationship souring and a pandemic year spent adrift, anxious and, well, uncertain of what’s next.

Needless to say, that future is not in Oak Park. (“You can’t even fly in, the flights are always delayed by weather ...”) Her father (a former Associated Press bureau chief at the Statehouse in Springfield) still lives in Oak Park; her mother (a nurse practitioner) divides her time between Forest Park and Mexico. Strong’s comedy (Second City, iO Theater Chicago) and musical theater roots (the Goodman, the Bailiwick) are still here. But most of her extended family lives in New York, and she’s dividing her own time between stays in the Hudson Valley, an apartment in New York City and her home in Los Angeles. The following is a shortened version of a longer conversation, edited for length and clarity:

Q: Let’s start with the book. You begin, on page one, so unsure of what you’re doing you write you don’t how to tell this story and don’t know what the story is.

A: And it’s still that way. At the beginning of 2020, in January, I lost my cousin Owen to glioblastoma (a form of brain cancer) and I didn’t really grieve it. I didn’t know how. It felt like there’s no way for me to talk about this yet. I will break down and everyone around me will break down. In March, the guy I was seeing got (COVID-19) and right after (the pandemic shut down “SNL”) I was home in my apartment for two weeks by myself, breaking down. I wasn’t able to write. On off-weeks (for “SNL”) I will at least be thinking of sketches. But I couldn’t write anything and was kind of swinging between anxiety and depression. Finally I booked an Airbnb to get out of the city and the day I knew I was leaving, in the shower, the first essay in this book hit me. I needed to write something down and in my rush I spilled my garbage and million tiny clam shells fell on the floor. I have always written for myself but never thought of a book. I sent what I had to some people got a nice response (and was later published by the online entertainment-news site Vulture). I’m not a poet but I’m very honest and if it was helping somebody, I figured I’d keep going, see what happens.

Q: Was there hesitancy to do a pandemic book — of all the loss, why my story?

A: Oh sure, I didn’t feel my story was special or worse than anyone’s. I didn’t want it to be all pandemic, either. I had all this time to examine past griefs I hadn’t processed. I have had other losses. But maybe there’s something about this age I’m at (37) — I didn’t have the shock of being 19, when you’re understanding your mortality for the first time. I was fully loving someone and their life then it was cut off. And I don’t know. I really don’t. Some people have read the book and said it’s a lot for one person, but I never felt that.

Q: Did you develop a pandemic routine?

A: Some days I stayed in bed. If there were any pattern, I took my dog Lucy out in the morning and took pictures. I looked through my pictures recently and every one was me outside with Lucy. I would write and then (she and friends she moved to an Airbnb with) would make dinner. We called it family dinner. We would have a discussion, cry, have more wine and a dance party then do the whole thing over the next day. I wrote a lot.

Q: Did your friends encourage the direction of what you wrote?

A: I didn’t want to rewrite much. I thought there was something about how the words came out that day, at that moment. I didn’t want it to be chore or job. I’ll sit and write and see what comes out. If I’m not a great flowery prose writer, maybe I could offer honesty.

Q: You didn’t write much about “SNL.”

A: Because it wasn’t what was in my head and heart during that time. I tried to touch on it some, it’s a big part of my life and identity, but it often wasn’t what I was thinking about. I mostly write about the “SNL at Home” episodes (coordinated from the cast’s homes just after the lockdowns) because, day to day, I was concerned about those.

Q: Did you want to do those episodes?

A: I did and I didn’t. I wasn’t ready by the first one. I pushed to have the (Vulture) essay come out because I wanted to respect my grief first. Certainly before I went publicly silly again. As far as the technical stuff (of those episodes), for me, it’s hard, it brings a new layer of stress — something that takes someone like five minutes takes me five hours.

Q: When the usual show returned you were off for most of the fall.

A: I was in Vancouver (shooting “Schmigadoon!”).

Q: So did it feel anxious to return that December?

A: Absolutely. I mean, I remember Bowen (Yang) and Fran Gillespie (“SNL” writer and former Chicago native) were writing a cabaret sketch that was set in a restaurant and I thought, “Wait, you’re serious? People are eating in restaurants right now? We’re New York, we’re supposed to do the right thing.” I just didn’t understand why anyone would go out if they didn’t have to right then.

Q: In general, did you like growing up in Oak Park?

A: I have never been good at feeling part of things all the way. That’s more me than Oak Park. I never felt I fully fit in. I went to Abraham Lincoln Elementary, loved that. I loved high school (Oak Park Forest Park High School). But I felt alienated the way teens do.

Q: You were expelled, at 15, when you were a sophomore, for possessing a small bag of pot. Did it feel like a personal rejection?

A: For sure, but also I was like a keep-your-head-down kind of student there. I didn’t want to be noticed, I didn’t like being singled out as a person. I loved school and part of my identity was being a good student. In my head at least, I was the student who could do a lot and my parents didn’t have to worry about me. But I couldn’t fight it. It was my pot.

Q: You were literally led out of school in handcuffs?

A: Yeah. We had a new superintendent who made it a mission to be very zero-tolerance. Which of course only got applied to some kids — not athletes. I just felt like “OK I’m just not important enough to this place.” Which is hard to feel at that age. I had two friends who were also expelled at the same time, and one of them was an athlete, saved this woman’s life on the Green Line, gave a kidney — he also got kicked out. I’m still considered alumni, though. I think.

Q: You transferred to Chicago Academy for the Arts.

A: Which was the best, because I seriously thought at that point: I’m not going to graduate high school. Which sounds crazy to someone for whom school had become so much a part of them. But art school — this is so corny, yet true — it gave me my smile back. I felt even better. I don’t know if it put me on my path — it didn’t get me into acting, I had been doing local theater around the city for a while by then — but it snapped me back into life, and just wanting to live again.

Q: What theater were you doing?

A: I took my first drama class at three. Then I did community theater in Oak Park. I did “Grapes of Wrath” at eight — I played Ruthie Joad, who was 12, which felt like a big deal. I started doing professional theater and got an agent at 11. It was much safer to be a child actor in Chicago than, say, in LA. I did shows at the Goodman, at the Bailiwick — I was in the first couple of seasons of “The Christmas Schooner” there. My first show at Bailiwick was “Pope Joan” in 1995. I was around 10. The last professional show I did before high school — when I didn’t do theater anymore — was during eighth grade and it was “Fahrenheit 451,” a musical at Bailiwick.

Q: Satiric, I assume.

A: You would assume! But it was not satiric, and it did not do well. I played Clarisse. (Sings) “I wonder what it’s like to be a fireman!” It was stuff like that.

Q: “Schmigadoon!” is set inside of a musical. Did those experiences prepare you?

A: Well, you do learn a bunch. But I was also just a fan of musical theater. Being in Chicago, we were doing musicals about the only female pope. And I did “The House of Martin Guerre” and my character was raped on stage every night — and I was 12. So, very different musicals than the kind (candy-colored Rodgers-Hammerstein musical) in “Schmigadoon!” My Uncle Ed is a theater producer in New York, my dad and I went to his shows and saw “Guys and Dolls,” “The Secret Garden.” I was into the soundtracks. I rented every musical on VHS they had at Video Magic in Oak Park.

Q: Are you leaving “SNL”?

A: I have no idea. I know that’s a boring answer. I go back and forth every day. Someone said, “Weak.” What am I supposed to say? There’s a couple things I want to do which would leave it open to do more “SNL.” Talking to Lorne, you understand: The show is different now, you can stay longer, do different projects. I don’t want to feel like I am getting stale or taking up space that others could use. There are a lot of reasons to stay and a lot of reason to leave, and I haven’t really figured it out yet.

Q: What do you want to do?

A: I want to leave it open. Like everyone in this business, I’m worried about my career: What’s my narrative? Am I done? Then the world cracked open and I didn’t know I could write a book or produce. So I decided to stay open, and see what happens and not beat myself for not being on the path I thought I would be on by now.

cborrelli@chicagotribune.com