'Schmigadoon!' Season 2: Cecily Strong, Keegan-Michael Key in gritty, greedy musical

The Apple TV+ series Schmigadoon! takes a darker turn for Season 2, putting Melissa (Cecily Strong) and Joel (Keegan-Michael Key) in Schmicago, based on musicals from the 1960s and 1970s.

“I've always known that I wanted to move through the different eras for different seasons,” co-creator Cinco Paul told Yahoo Canada. “So then I started to look at the musicals and thought, what is the journey for Josh and Melissa this season? Because I didn't want it to be about the relationship, I wanted them to be a team now.”

“Last season was about love but this season is going to be about happiness, because there was very little happiness to be found in any of these ['60s and '70s] shows. … They're trying to find joy in a world that has no happy endings, and that's the world that you and I live in. So there was a lot that resonated there with me and with everybody else who was working on the show.”

What is 'Schmigadoon!' Season 2 about?

Back with its impressive cast, including Cecily Strong, Keegan-Michael Key, Ariana DeBose, Dove Cameron, Kristin Chenoweth, Alan Cumming, Jane Krakowski, Aaron Tveit, Ann Harada, Patrick Page and Jaime Camil, Schmigadoon! begins with Josh and Melissa returning to New York.

The couple are newly married but are facing one upsetting issue, they haven't been able to conceive a child. Then they have the idea to go back to the town of Schmigadoon, where everything and everyone is happy. But things take a turn when they don't go back to Schmigadoon, they end up in Schmicago, filled with crooks, showgirls and greedy villains. There's nothing idyllic about Schmicago at all, but now they're trapped, and they have to find their happy ending in order to leave.

"I liked the story arc of somebody that's maybe not feeling so great about themselves at the moment, for whatever reason, it's something that everyone can relate to," Strong told Yahoo Canada.

If you're not really a fan of musicals, you may be temped to write off Schmigadoon! as something that's just not your taste, but that certainly may not be the case. Season 2, in particular, really amps up the comedy in a way that can appeal to a musical averse audience.

For Paul, he learned in Season 1 that he very much likes to stick to the script, but with impressively talented comedians and improvisers in the cast, primarily Strong and Key, he did give them some room to give scenes their own spin.

“I think if it were up to Keegan and I, I mean, we'd improvise half of the show,” Strong said. “I think what's nice is we have a good relationship with Cinco and we love what he writes.”

“So we try to stick to the script as much as possible, but he's very open if we have some suggestions. Not that they'll use them all, and they're not wrong for maybe not using all of them, but we can't help ourselves and we'll just keep going. We called ourselves the button twins, we will have 18 different endings.”

“The other thing is, within the confines of this really fantastic writing, we would find little things we could do,” Key added. “I do an impersonation of Patrick Page and so within the lines, if I had an opportunity to do a line in Patrick's voice, I would do that.”

“[My] acting technique is, can I make [Cecily Strong] laugh?”

'We're bringing the camera on stage with us'

But of course, we can't talk about this series without mentioning the musical numbers in the show, which are bigger, bolder, funnier and sexier than Season 1. The original songs also very much fit the mold of a '60s or '70s musical.

“I wanted the songs to sound authentic,” Paul said. “I wanted them to have the same instrumentation that the originals had.”

“I want the songs to feel like, 'oh this is a Stephen Sondheim song I've never heard before.' Or 'oh this is a Stephen Schwartz song that must have been cut from Pippin,' or something, … which I call the highest level of parody or satire you can get.”

Continuing from Season 1, the musical numbers are filmed with the actors singing live as much as possible, because Paul wanted to prevent any evidence of pre-recording that could take the audience out of the moment.

“I don't know if this is just because I'm a glutton for punishment, but if somebody asks me to lip sync to something that's already been perfected, and I pre-recorded, I feel like I'm cheating,” Dove Cameroon said. “There's something about it where I'm like, but I could do it live.”

“We're going to take all of these incredibly talented people, showcase the best of their abilities, and do it live and let the audience see. In stage performances, you don't actually get to see the twinkle in the eye if you're further than row three. ... So it's just really intimate, and it's really, really fabulous for that reason.”

“I think the result is there's just a seamlessness to the way that it's being told,” Aaron Tveit added.

“I almost feel like we're bringing the camera on stage with us. The audience is getting to see kind of what we see, which is really incredible.”

Jane Krakowski has a particularly impressive number called "Bells and Whistles" that has her doing impeccable tricks as lawyer Bobbie Flanagan, based on the Chicago character Billy Flynn.

“I was particularly excited because the musicals of the ‘60s and ‘70s are my favourite musicals and the ones that had the largest influence on me,” Krakowski said. “I was beyond thrilled when I saw that I was going to be Bobby Flanagan, it's an incredibly custom-written role for me.”

“I literally got to put in all the bells and whistles of anything I've learned how to do throughout my career. It demanded it and I was thrilled to step up to the plate to fulfill it with the special skills on my resume. ... It was a bit like getting as much as we could before they pulled the plug on filming that day.”

Cameron also has a Liza Minnelli in Cabaret-inspired number, called "Kaput," which is another highlight of Season 2.

“It started out pretty grand from the jump. ... They told me it was going to be lots of chair'ography and I was going to have to learn a couple of hat tricks, and I was going to be nearly naked. And I was prepped from the jump,” Cameron said. “I was definitely nervous about the whole thing, but thankfully, we got to shoot it at the very end and got some good rehearsal time.”

“I am by no means a dancer like Liza, I was never going to get anywhere close to that. But I think the thing that I find so fascinating about Liza on stage is she just has so much work in the eyes. There's such a sense of humour in the eyes and a sense of wonderment. She's really looking at every member of the audience as though they were either her best friend or her lover, or target or something. There's an intrigue that she has and I think that was something that I wanted to do.”

The comedy also extends into the musical numbers, primarily with one called "Everybody’s Gotta Get Naked," with Tveit and Key channelling the hippie era of musicals.

“One of the things I've learned on this show is that the best choice at every moment is always the most ridiculous choice," Tveit said. "So that number just kind of personifies that."

"If you think, oh I don't know what to do here. It's like, well what's the craziest thing that I could try to do? Or the silliest thing that I could try to do. And I think we all did that for that entire number.”

What musicals could be next?

Following an impressive second season, the next question is, where could Schmigadoon! go next? The cast and crew have a few ideas.

“I do feel bad, I really wanted to do a parody of The Wiz in this season, and I couldn't figure out how to get it in there,” Paul said. “Ease On Down the Road was a song that was on my playlist and I targeted.”

“But beyond this, I'm such a huge Stephen Sondheim fan that I would love to do Sunday in the Park with George and Merrily We Roll Along, and Into the Woods. ... We'll see what happens.”

Krakowski echoed Paul's feelings about something Sondheim-related in the future.

“Wth the loss of Stephen Sondheim, I feel that we could do an entire season just honouring Mr. Sondheim,” Krakowski said. “I know Sweeney Todd is one of his Cinco's favourite musicals, and my favourite musicals are both written by Stephen Sondheim, which are Gypsy and Sunday in the Park with George.”

“I would love to hit the [musicals] that I feel changed me musically when they came out, in the history of musical theatre, like Rent and Spring Awakening and Hamilton."

For Ann Harada, she wouldn't be opposed to stepping back into her Les Miserables shoes for the series, in the future.

“We talked about this all the time, if there was a Season 3, it would have to be for musicals of the ‘80s and ‘90s," Harada said. "I would be so down to be in [Les Miserables] again, or [The Phantom of the Opera] or Cats, or any of those kinds of [big shows].”