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Nov 17, 2021 By Matt Conner Web Exclusive

Twenty five years is perfect according to Alison Klayman.

A quarter-century has passed since Alanis Morissette blew away expectations and crashed through glass ceilings with the powerful and uber-popular album Jagged Little Pill, a release that won a Grammy for Album of the Year and has since sold well over 30 million copies. It launched a host of copycat artists not to mention the way it’s settled into popular culture in the years since. There have been issues and reissues, an acoustic re-recording and now a Broadway production. Now you can add Jagged to the list.

Jagged is part of Music Box, a new documentary series premiering on HBO this week in collaboration with The Ringer’s Bill Simmons. Forthcoming docs will feature DMX, Kenny G, Saturday Night Fever, and Juice Wrld, but Klayman’s exploration of Morissette’s Jagged Little Pill anchors the release schedule.

We recently sat down with Klayman (who has also directed Ai Weiwei: Never Sorry and The Brink about Steve Bannon) to hear more about her own fandom for Alanis and the challenges of highlighting an album so well known by the masses.

Before we talk about your experience of making Jagged, I was curious how you came to this project in the first place?

Based on my track record, I was introduced to Bill Simmons and The Ringer and their journey with Music Box started a year or two prior, getting the whole concept together with HBO. I was told that Alanis was potentially interested in doing a film and they asked if I was interested in that project. My face transformed. I was like, ‘Oh, my god.’

Jagged Little Pill was my first CD I ever bought. My first cassette was Salt-N-Pepa’s Very Necessary. This whole time I’ve worked on it, I got the physical CD from my parents house and played it. I used to put it on my boombox and lie on my bed and I remember distinctly listening to it that way. Of course it was on the radio, so I’d listen to it all kinds of other ways, but I’d lie on my bed with the liner notes open and listen that way. It was that kind of decompression that it made.

It’s always been a dream to do a music documentary for me. I grew up playing classical piano and the musical side of filmmaking is one of my favorite parts. I’ve done a lot of artist films and I see this film in that vein. But doing a music film is a dream come true.

There’s been so much material produced around this album with anniversary reissues and the musical as well. What challenge did that create for you to produce something else about it in a meaningful way for a culture that likely feels like they know a lot about it?

For as much as I know every lyric of every song on this album, I didn’t know a ton about Alanis. I think its’ something about the kind of fandom there was in the mid-‘90s or maybe my age and the way I interacted with it. But the way I knew the album inside-out, I didn’t know the story behind it. I wasn’t that level of a fan.

Maybe it’s a good thing I wasn’t too intimidated by doing it, because I thought it was a film that should come in a celebratory manner. As a fan of the album, I know I was here to celebrate it. I wasn’t intimidated by other fans and what their expectations were. But I just felt like there was so much there to discover for me. That’s what draws me to projects in general is feeling like there’s something new to discover.

The 25th anniversary aspect of it all, which was part of the concept in the beginning, was actually part of the way we framed this work. I felt like the special sauce of this film was two-fold. One was the immediacy was having this access to this incredible archive. We didn’t know what was in it! We knew she had a lot of material but until the lockdown was light enough that we could go out there and begin the process of digitizing, we didn’t know exactly what was in there. But we were told there was a lot of archive.

So we could tell it with immediacy but also there was the retrospective lens, which I think is different than all the other ones. With a five-year or 10-year, this album has been re-released. I think there’s even been a Starbucks co-branded release at the 15 or 20 year mark. But I think there’s something about 25 years. We’re just starting to figure out what the legacy of the ‘90s means today. I think also being on the other side of “Time’s Up” and “Me Too” as well—that wouldn’t have been the case in previous anniversaries.

There was a sense when I started to talk to Alanis and others too that made 25 years feel like a magical number. Some things could be said and reflected upon that would be fresh and new. So we knew we were showing things direct from the source that were either in the moment or it’d have this 25-year reflective period.

You mentioned being such a big fan. Did that ever become problematic or did you come to this with enough experience that you could remain distant in ways you needed to be?

I felt like I was able to come to this as a fairly seasoned professional now. I definitely think of how my middle school self would not believe that I was doing this, but what was really amazing to me was how much fun it was to make it. The fact that I’m interviewing people and being able to talk about the songs, that it was the assignment—

That you could just geek out?

Yeah! There’s that part, maybe you’re right, where you wonder if you’re doing a good enough job because it’s just so fun. But then you realize, ‘This is the job!’

I wanted to ask about the interview aspect of it. How was that part of the experience?

I think with Alanis’ interview, it was the first time I’d ever had a two-day interview. It was the first time I’d hate that long of a master interview. I’ve done these really in-depth portraits before or follow docs. I’ve spent a lot of time with a single figure, but none of those films were constructed around a key interview that way. It’s so much more vérité and off the cuff.

I love the fact that on the first day, we covered everything up until Jagged Little Pill and then the second day was all about the album. I thought that was cool. When I thought about it, I thought it was just easier for people to go through things chronologically and it makes sense that we’d talk about 19 years and then two years. It felt like a good balance and that I got to know so much about who Alanis was when she came into writing the album.

Nineteen…

Isn’t that amazing? When I was little I thought she was so grown. Looking at it now, you’re like, ‘You were so young!’