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Unbreakable Kimmy Schmidt: The Secrets Behind Season 2's Awesome Songs

How Jeff Richmond created their own Great American Songbook and more

Joyce Eng

Unbreakable Kimmy Schmidt composer Jeff Richmond is well aware he's not squeezing everything he can out of the show. "I've got to talk to someone about a soundtrack," he tells TVGuide.com. "It's true. Every other show that barely has any music puts out a soundtrack and yet we never do. We're missing revenue income!"

There's certainly enough for a double album -- or in Kimmy (Ellie Kemper) and Titus' (Tituss Burgess) case, a double Columbia House cassingle -- between Season 1's addictive earworms and the hefty batch of hilarious new songs in Season 2. "This happened a little bit in 30 Rock too, where it can be fun and successful and we embraced it even more so in the second season," says Richmond, who also serves as executive producer with his wife Tina Fey and Robert Carlock. "The songs are just fun for everyone. We love music here and these guys always find ways to get music in there so I have stuff to do."

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Sometimes it was as simple as a sweet little ukulele song between Lillian (Carol Kane) and her one that got away, Bobby Durst (Fred Armisen), or the Bunny and Kitty theme. Other times, it was as big of an undertaking as translating a song into Japanese for Titus' past-life geisha or creating fake Broadway tunes for a fake Great American Songbook. "The Great American Songbook in Episode 5 was certainly the most fun thing for me all year," Richmond says. "I listen to a lot of musical theater; I play a lot of it. I really embrace it. Having played piano in improv theater so much, people tend to make up songs and you would find different ways to do musical theater styles. I'm kind of a musical theater geek, so I was completely in my element."

The idea for the Great American Songbook was born out of a desire to have Burgess, who boasts a four-octave range, sing more after his "Peeno Noir" breakthrough. Wanting to incorporate music organically, the writers landed on Titus expressing his happiness about his new relationship with Mikey (Mike Carlsen) through song. "It felt like a fun way to do it ... that he was singing these songs and then he's going to teach Lillian these songs that supposedly everybody knows," Richmond says. "There's always something great about continuing to build what this fictional world of entertainment is that is around the show.

"For some of them ... they had some pretty rough lyrics," he continues. "And this happens often with comedy writers -- they're so skilled at writing their jokes and they have such funny, wonderful thoughts and ideas of couplets, and then you get it and then you have to kind of shape it to feel like it would sound like a song from the American Songbook would. So I took it and Tina took it and we shaped those a little bit more."

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Below, Richmond takes us through crafting the Songbook and the season's other big tunes -- plus his very early plans for Season 3.


"A Glorious Morning" from Alabama!
The first pseudo-standard Titus croons is a track from the black version of Oklahoma!, aka the musical that would've been his big break if it weren't for his nemesis Coriolanus Burt (James Monroe Iglehart). "He mentioned it in Season 1, so we were already down that route," Richmond says. "I love that it sounds like a normal song about a beautiful morning and then the twist comes." (Sample lyric: If I don't mind never voting / Or my church burning down while I sing / Oh, the cropper and the Klansman should be friends) Though he admits there was initial trepidation about possibly besmirching Rodgers and Hammerstein's great name, they quickly got over it. "We were like, 'Are we taking an unnecessary swing at Rodgers and Hammerstein in this episode?' As a musical theater person, Richard Rodgers is one of my favorite composers," he says. "But I think, I hope, everyone knows it's all in lighthearted fun. It's more about the bigger picture of the whole episode. It was once again us delving into racism a little bit."

Theme from Feels Like Love
"The Miracle Worker stole all its thunder," Richmond quips about the Helen Keller-inspired-but-unauthorized musical. While Burgess sang "A Glorious Morning" a cappella, Richmond decided to slowly phase in actual music starting with this tune. "We knew Titus was going to be singing organic songs and at some point, we made a decision, are we going to accompany him? 'Yeah, I think we should.' When he starts to sing these songs, we'd find a way to slowly bring in the strings, which is what we did on that one. As the episode continues, he's wrapped more and more in strings or his own ability to play the piano. Tituss really plays the piano, so that was another reason why we wanted to go that route, to show off another Tituss Burgess skill. He's a really talented piano player."

"Stoop Crone" from Croon, Crone, Croon! and "Ordinary Gay" from We Three Marionettes of 1971
Titus tickles the ivories starting with snippets of these two songs, the former of which, according to Titus, was reworked into another Rodgers and Hammerstein classic, The Sound of Music. "It was really fun to work on those because I wanted each one to sound like they were written by different people, and it's fun to follow not just actual musical theater style, but the style of different composers," Richmond says. "It was like, 'Oh, this one will be a Maltby and Shire piece -- 'I'm just an ordinary gay' -- and it follows a Rodgers and Hammerstein-like song. Maybe my fellow musical theater nerds can pick up on the differences."

"You're My Baby Now" from Daddy's Boy
"Peeno Noir" gets all the deserved love, but the true underrated gem of Season 1 is the title track from everyone's favorite unfinished 1938 musical Daddy's Boy. "We had to bring it back," Richmond says. Instead of a verse or a chorus or two, we are treated to a full version of "You're My Baby Now" -- a father's declaration of his "innocent" love for his infant son -- for which Richmond recruited his friend, lyricist Michael Thomas, to pitch in. "We took what the writers had laid out, which had been Dylan [Morgan] and Josh [Siegal], and we just took it much further and added more verses and choruses. They needed to be extended more than the fragmented pieces of the other smaller songs," he says. "That lyric where you think it's going to be 'naughty little ass' but is actually 'naughty little... personality' was all Michael Thomas. Jefferson Mays came back to sing it. He's a great guy. He'll just pop in if we need him. He looks like he's from that era and his voice is perfect."

The full song plays over a montage of lovesick Kimmy helping Dong (Ki Hong Lee) and his green-card wife, Sonya, fake a photo album to fool immigration authorities, which was always scripted that way. "I think it's funny because the tone of the montage -- that story line isn't fun or happy; it's kind of sad, but with that music under it, it kind of has a weird, brighter take," Richmond says. "It was fun to approach it that way. [At the end of the song] the boy grows up, and it is sad. We added those lyrics at the end. Now it's sad for everyone. It works on all levels."

But really, the most important question here is: Will there be a full Daddy's Boy musical? Both Richmond and Carlock have previously told TVGuide.com that they're up for it. "I'm telling you, we've got to go to Netflix," Richmond says. "We've got three solid songs now. We do a couple more and you've got a first act. I was saying we should talk to Ted [Sarandos, Netflix CEO] and say, 'We should do it, right?'"

Theme from Stephen Sondheim's Pinocchio
"The ringer to me in that whole episode is Titus playing outside on the piano that very sad, dark ballad, and you find out it's Stephen Sondheim's Pinocchio!" Richmond says. But the song wasn't originally Sondheim or Pinocchio at all. "That was a solid Tina song. I think Tina actually lyric-ed that whole song and it was originally called 'The Gentleman's Rapist.' I said, 'Oh, no, 'The Gentleman's Rapist'! You know, I think you can top that. Go sweet with it.' And she came up with Sondheim's Pinocchio, which is perfect. It tickles me every time."

"Just Go On" from Gangly Orphan Jeff
The episode's denouement is another full number -- this time from the ill-fated musical that opened six days after Annie -- for which Richmond enlisted Michael Thomas' help again. "It's supposed to sound like a big Charlie Strouse piece. I'm going to take credit that it sounds like it's from Annie," Richmond says. "I think what makes it even sound more like it's from Annie, right before we mixed the episode, I said, 'Oh, when Lillian starts talking, we should bring in the little musical intro,' and for some reason, when you start to play it on an actual instrument, it really did sound like you were going into 'Tomorrow.' It was pretty funny."

Right now, "Just Go On" and "You're My Baby Now" are the only completed songs, but if Richmond had his druthers, that'll change soon. "It's so often in the world of comedy, you don't get very far with songs. 'This is all we need for the comedy of it,'" he says. "Maybe we'll nail Tituss down this summer and we'll finish all those songs and we'll have him put out an American Songbook. I think we should do that."

Songs from Now That Sounds Like Music!
Kimmy Schmidt goes full 30 Rock in Episode 9 with a hashbrown-amazing gag of rip-off songs of well-known hits. Richmond says all the credit for turning Night Ranger's "Sister Christian" into Dusk Mountie's "Brother Baptist" and R. Kelly's "I Believe I Can Fly" into Art Smelly's "I'm Convinced I Can Swim" (from the movie Earth Jelly) goes to writer Meredith Scardino. "They kind of knew who we wanted to legally bend those songs around to be. We didn't change a word," he says. "They sound as poorly as she wrote them and I think they're hilarious. I use the same couple of singers every time. The read-through was at like 1 o'clock in the afternoon. We got the script and got the singers in at 8 o'clock the morning of the read-through and said, 'OK, we're going to knock these out really quick and they did it.'"

The show cleared all the original songs, which include Katrina and the Waves' "Walking on Sunshine" (Kartuna and the Wigs' "Hiking on Sunlight"), Hanson's "MMMBop" (Shanson's "YUMBip") and Eric Carmen's "All By Myself" (The Error Car Men's "I'm Freaking Out"). "We had their permission that we were kind of doing these original songs and changing the lyrics, and whenever you're going down that road, there are so many people who have publishing rights on all those songs and it's just crazy," Richmond says. "It takes forever to get those songs cleared."

Unfortunately, though he doesn't remember which ones, there were a few songs that didn't clear for whatever reason. "But everybody else was very happy to make some money off their songs. And who would blame them? It's hard to make money off of music these days. Charge your songs for parody!"

"Ding-Dong Diddly Ding-Dong Do" from Kimmy's happy place
The pitch-perfect, violent Disney parody of Kimmy's fantasy haven in Episode 10 had been brewing since last season. "We had kind of set her up in Season 1 that she had a fantasy world about Disney," Richmond says. "The cool thing, and it's in the script as well, are the parallels of her life with actual Disney princesses, when you really kind of dissect it and deconstruct it. They're very similar compared to a woman who lives in a bunker. It kind of made sense that she would have this fantasy world." The original lyrics were in the script, but after the table read, the consensus was that the tone was off. "It seemed a little more like an Alan Menken -- one of those songs that's like, 'somewhere that's wet,' 'I wanna get outta here.' But that's not what she's doing. She's embracing everything that's going on in her world, so we did the 'Bibbidi-Bobbidi-Boo' thing. I ended up working on that quite a bit to get that lyrically working the right way with the writers."

When it came time to record, there was a brief discussion of dubbing Kemper's voice, a la old-school Disney films. "They went back and forth -- 'Oh, should we do it like they used to do where someone else actually sings the part of the princess so she would have this really operatic, princess-y voice and not use Ellie's voice?'" Richmond says. "And we were like, "No, no, Ellie's gotta do it." And she wanted to do it and she sounds great. She did a great job. She's Kimmy. It couldn't have been anyone else."

The Reverend's song from Kimmy's happy place
It's not a true Disney movie without a foreboding villain anthem. After writing the first few lines of The Reverend's (Jon Hamm) tune, Richmond decided to ask Hamm if he'd like to sing it himself. "The evening before ... I sang it into my phone. And I said, 'Jon, do you think you can sing this?' And he of course was so willing and he came in and sang," Richmond says. "He had a couple of his own little lyric adjustments, which were great. He wanted to sing 'freaky, funky fella,' and I said, 'Great, do it!' He sang it and we built the orchestration around what he sang. That whole sequence -- the music was a real challenge. It had to sound big and it had to sound like Disney. That involves bringing in a lot of players and musicians, and recording sessions, and it all came out pretty great, I think. ... Once again, there should be a full version. Hamm should come in and do it. He got slaughtered [in the scene] before he could finish it."

"Outside Bones"
Titus' hilarious, flu-stricken improv audition piece about teeth in Episode 12 was written into the script. "It's the funniest thing ever. Bones on the outside of your body?! Horrifying! I had nothing to do with that," Richmond says. "I sang it to Tituss once. 'I think it goes like this, Tituss.' That's the other great thing about Tituss -- he's just a machine. 'I think it sounds like da-da-da-duh-duh,' and he says, 'Got it.' And he just does it." Richmond cameos in the scene as the piano player, "pretending to try to catch up to him." And yes, it's supposed to be his character, Alfonso, from 30 Rock. "[He's] now just playing audition piano on Broadway now that the TGS show is no longer on the air. In some universe, that's what that is! Maybe next season, he'll be on the cruise with Titus."
So what kind of aural amazingness do they have planned for Season 3? Nothing concrete yet. But Richmond has some ideas. "We didn't get to do actually do some kind of parody of Hamilton. There is a solid joke -- he couldn't rap or walk in a circle, I think Titus says -- which is hilarious. But next year, guess what's not closing on Broadway? Hamilton! Maybe we'll do it. I have not heard anything yet. But I hope they keep giving me work so I can keep playing some tunes."