'Pen15' Music Supervisor Unpacks The Show's Y2K Soundtrack: Mandy Moore, Spice Girls & More

Alex Lombardi/Hulu
Maya Erskine and Anna Konkle in PEN15.

Tiffany Anders breaks down key scenes featuring music from Lit, Nelly and Des'ree... and a wish list for a potential second season.

If you’re one of the lucky millennials who survived middle school in the early 2000s, Hulu's Pen15 is equal parts hilarious, nostalgia-inducing and totally triggering.

Set in the year 2000, the series stars comedians Anna Konkle and Maya Erskine (who created the series along with Sam Zvibleman) as fictionalized versions of their seventh-grade selves, in a world where notes are still written in gel pen and an earring is the hottest accessory the cutest boy in class could have. But there’s a gag: the two stars of the show are in their early 30s, while the classmates, crushes and mean girls populating the halls of Trailview Middle School are played by actual 13-year-olds.

The series naturally features more songs from the era than you can fit on a mix CD. From boy bands and girl groups to pop-punk and club-ready hip-hop, Pen15 music supervisor Tiffany Anders was tasked with capturing the soundtrack of growing up before social media, smartphones and Snapchat filters eclipsed the simple joys of choosing an AOL screen name.

“Producers actually reached out to me because I worked on a show for Netflix called Everything Sucks!, which was set in the mid '90s,” Anders tells Billboard of how she became attached to the project. “And I got the script of the first episode and was totally in love with it. I thought it was hilarious.”

For the veteran music supervisor, whose credits also include the FX series You’re The Worst and Facebook Watch original Sorry for Your Loss, the show’s most cringeworthy moments needed to be combined with a sentimentality to guide the collaborative process of choosing songs.

“There was so much that I related to from my junior high experience, even though I'm quite a bit older than the girls,” she says. “I would give them things that they kind of forgot about. We used a Naughty By Nature song in the last episode, and they were like, ‘Who's Naughty by Nature again?’ So that was kind of funny. There was stuff that we got to go back to that was fun to revisit.”

Anders shed some insight into the show’s biggest (and most awkward) musical moments -- from filtering racism through the lens of Spice Girls to curating the perfect middle school dance. Warning: spoilers ahead for those who haven’t seen the show.

SONG: Mandy Moore, “Candy”

SCENE: As the pilot opens, Maya and Anna anxiously plan out their first day of school outfits together over the phone and make a pact that seventh grade will be the best year ever.

Anders: "So, that first episode was loaded with songs of the time period, and 'Candy' was one that the girls weren't so sure about. They asked me to find some [alternatives] for it -- and the director, he put in that song -- and I said to them, 'You know what? I don't think we're going to get better than this. This is really, really great.' So that one actually took the longest to get approved, but I felt like it was a really, really strong opening and really kicked off the whole episode beautifully. We kept it very song-heavy in that first episode, because I thought it was a really nice way to introduce the time period and the girls and the setting."

SONG: Lit, “My Own Worst Enemy”

SCENE: Maya and Anna confidently take their first steps of seventh grade (at the exact same time) before nearly being run over by a skateboarder.

Anders: "['My Own Worst Enemy'] was something that was on our playlist before they started shooting, so it just happened to work out really well in that scene. I think there's an energy to them putting down their feet and walking in and going into a whole different world. The energy of the song, it feels kind of cooler... From 'Candy' to Lit, it's like they're stepping into the next level of growing up."

SONG: B*Witched, “C’est La Vie”

SCENE: The girls hatch a plan to win backstage passes to see Irish girl group B*Witched by calling their local radio station.

Anders: "I suggested that we use the song, but we thought it was enough with the girls hearing the other kids singing it in the school hallway. We had to figure out spots where it was really important to use these big songs, and I think them referencing [B*Witched] felt like enough that we didn't have to license a song. Although, who knows? If there's a Season 2, there might be tons of B*Witched in it!

"Maya and Anna brought B*Witched up and asked, 'Do you remember that band?' And it was just one of those weird things that felt really good for the characters. And it would be a good nod to something that we all may have forgotten about, but will remember when we hear the name B*Witched. And there were a few others that I had suggested to them as well that were similar -- like S Club 7 was on there. I mean, we really went down the rabbit hole. There were actually quite a few of those pop bands at that time, right at the tail end of the ‘90s. And then further into the early 2000s, which would kind of be nerve-wracking to us because we couldn't use, say, Avril Lavigne since that was all 2001/2002. So we were just kind of missing those... which would've been great, but gotta keep it real!"

SONG: Spice Girls, “Say You’ll Be There”

SCENE: The girls film a class project about osteoporosis as the Spice Girls, which inadvertently leads to Maya's eyes being opened to casual racism.

Anders: "[Maya and Anna] had that in the script, so they definitely knew that it had to be the Spice Girls. So it was a matter of working that out and figuring out which song -- they ultimately decided they wanted 'Say You'll Be There.' We got a little creative with how we used that, because we didn't use the original master. In the backyard scene, I said, 'Wouldn't it be good if it was like a karaoke version that you're singing along to?' So we got a little sneaky on that one.

"The race thing that's in the whole storyline was part of the reason that they wanted the Spice Girls. I remember actually thinking when the Spice Girls came out, you know, like, 'This is so weird that there's these kind of Barbie doll girls, and there's Baby Spice and Posh Spice.' I mean, it's just so bizarre when you look back on it. It really lined up what they wanted to do story-wise with Maya and the racism that's happening to her, and kind of processing that as a young girl. It just worked perfectly."

SONGS: Nelly, “E.I”; K-Ci & JoJo, “All My Life”; P.O.D., “Rock the Party (Off the Hook); Naughty By Nature, “Jamboree” feat. Zhané; Big Punisher, “Still Not a Player”

SCENE: Maya and Anna experience the various traumas of their first middle school dance, from grinding and slow dancing with boys to fighting with your best friend.

Anders: "We definitely wanted the Nelly and the K-Ci & JoJo -- those were must-haves for us. When Brendan (Brady Allen) shows up to the dance and he's got the Limp Bizkit shirt and the make-up on, that was a harder thing, because we needed something that was totally opposite... We were trying to be shocking with that moment. We tried to get Limp Bizkit and could not get it, so we had to find something else, [P.O.D.], that just was jarring for his arrival. And then there were a few other things that I recommended to them, that we used a Big Punisher song for the end of the dance scene and a Naughty By Nature song that came out just in time in the year 2000. So we used a couple other things to make the dance kind of diverse with the grinding scene and these really romantic, overly sexy songs that were kind of inappropriate, but kind of also weird milestones we all experienced at that age."

SONG: Des'ree, "You Gotta Be"

SCENE: After being rejected by the popular girls and her crush during their first middle school dance, Anna makes up with Maya via a choreographed dance sequence to their song: Des’ree’s “You Gotta Be.”

Anders: "That was the hardest episode, and we all knew it was going to be. There was a lot of back and forth about what the girls could dance to, what would be their song where they break out and do the dance together. And at some point, Maya and Anna were like, 'Just give us your craziest ideas.' I think what was really important with the Des'ree song is that there's an emotional weight to it. They've gone through all this stuff together as best friends do at that time, and it’s them coming back together with that song. It's a song of the era, it's kind of an adult song and it's meaningful in a way... It wasn't a teen pop song like a B*Witched track or a Spice Girls track. It had some emotional weight to it, and the fact that it brings them together, even though it almost seems like an odd choice -- it really works for that scene and kind of makes you feel a tenderness for them. I think it was really important that we [weren’t] just playing all jokes, and we were really keeping the emotion of the two girls and their story and being attached to them. So I personally loved that we used the Des'ree song there."

SEASON 2 WISHLIST

Anders: "Oh gosh, we have so many! Marilyn Manson...I think Enya was probably the biggest one that we all wanted. Backstreet Boys, Papa Roach, Sublime. Lots of hip-hop, like DMX -- all these songs that we kind of wanted but didn't quite make it into the season.  If we were to jump forward a year or so, definitely Avril, which I kept going back to again and again. Depending on what the scripts are like, I think it's pretty safe to say those might show up somewhere in a Season 2. If there’s a second season, I think it will be just as fun as this one."