Lisa Loeb in 1994
Photo by Gary Gershoff/Getty Images
Making Heads Or 'Tails' Of Success: Lisa Loeb Celebrates 25 Years Of Her Major-Label Debut Album
"We have an audience for a song," singer-songwriter Lisa Loeb told Entertainment Weekly in the fall of 1995, "I hope they want to hear a whole album."
As the first unsigned artist to hit No. 1 on the Billboard Hot 100, Loeb was situated within the unique position of having to balance the television-and-radio promotional whirlwind around her platinum-selling single "Stay (I Missed You)" from the Reality Bites soundtrack, while also recording her major-label debut album for her recent signing to Geffen Records. From indie rock bandleader and solo acoustic troubadour to labelmates with pop culture juggernauts like Nirvana, Aerosmith, Guns N’ Roses, Hole and Weezer, all eyes were on Loeb to see how she would follow up her massively successful, charting-topping single.
The charmingly up-to-the-task result was Tails—her first of two back-to-back Gold-selling albums—which celebrates its 25th anniversary this month. Loeb will be commemorating the event on Saturday, September 26, with her "One Night Only World Tour"—a special two-show live streaming event where she will perform the entire album acoustically for the first time in her career.
To help mark the two-and-a-half-decade milestone, GRAMMY.com recently hopped on the phone with Loeb to discuss making her Tails album amidst the meteoric rise of "Stay," navigating "acoustic guitar equals folk music" pigeon-holing, and releasing her most recent album, A Simple Trick to Happiness.
Lisa Loeb: Since Tails was my first major-label album, like a lot of artists in that position, it was an assembly of songs that I had written over the previous few years that I now wanted to share with a larger audience. Some of the songs I was most excited about re-recording or working into a fuller band context had already appeared on other recordings I had made. That was not just the case with Tails, but also with my next album, Firecracker. When I was making records back in college, I knew it was time to make a new album every time I had a collection of 12 to 14 new songs. So, the biggest focus of that time period was just buckling down and recording them for my new album. Working with Juan Patiño, my co-producer, we had already done a lot of demo recording of these songs before "Stay" had even come out.
Even without an album release, the expansive mainstream success of "Stay" required Loeb to maintain a busy datebook of appearances—The Late Show with David Letterman, the MTV Beach House, picking up International Breakthrough Act from Tom Jones at the 1995 Brit Awards—throughout the latter half of ‘94 and well into the summer of ’95. All the while, Loeb and Patiño were spending as much time as they could recording and re-recording the songs that would comprise the Tails album.
Lisa Loeb: During that period, it was important for me to promote "Stay" and do some touring and appearances around that, but to also make sure we were recording the best versions of the songs for my new album. Juan and I tended to go deep into the production side of things. We’re both perfectionists, or in a kinder way, I’ll say that we were quality-control freaks. I’ve heard us compared to people like Don Henley and Fleetwood Mac, where production is very labor intensive and detail-oriented. We wanted it to feel easy and natural, but we also had very specific ideas of what it should sound like. We were very intense about the whole process. Plus, since it was my first major-label album, we bought into all the stories of our favorite bands and felt like it was such a big deal. I wanted to maintain my grassroots following that I had built but having a major-label deal meant a lot and we were very reverent to that idea. We wanted to live up to that "major-label debut" hype.
That "major-label debut" hype came courtesy of Loeb signing to Geffen Records, the victors of a multi-label bidding war centered around the up-and-coming star. However, instead of all of the attention being paid to just her recent hit, it was one industry vet’s connection to her early material that was one of the major contributing factors to her decision to finally sign with Geffen.
Lisa Loeb: Geffen had an A&R person named Jim Barber and he had shown interest in my music for years—way before we actually signed with them. It was a combination of his interest in me before I had a No.1 single and the fact that I thought Geffen Records was super cool for their intentional mixture of pop and indie music. I felt like I was somewhere in the middle of that: I was definitely an indie musician and leaned towards that genre, but I also had this one song that had become very popular. So sometimes I was treated like a pop artist, which, back then, there was more of a divide between indie and pop than there is today. I also liked David Geffen as an entrepreneur and his feel for making a major label feel like a boutique label.
As the finishing touches were being put on Tails for a late September ’95 street date, Loeb released "Do You Sleep?" as the album’s lead single. The song quickly became a Top 20 Billboard hit and Loeb performed it (alongside "Stay") on a Chevy Chase-hosted episode of Saturday Night Live less than two weeks after Tails was released. For the song’s music video, Loeb relied on her focused creative vision to collaborate with GRAMMY-winning director Sophie Muller (No Doubt, Garbage, Beyoncé).
Lisa Loeb: Sophie had worked a lot with Annie Lennox and she had just done Hole’s "Miss World" video. There was always something very sparkly in her videos. My sister and I worked with Sophie and came up with a concept that was originally a little more abstract than the finished product turned out to be. I was working with a designer so that I could get my clothes exactly the way I pictured them, so I was completely involved in making and wearing the clothes I wore in that video. When we got to editing, the initial version wasn’t edited on the beat, and it was confusing to my brain. So, Juan and I went back in and re-edited it. In retrospect, I wish I could’ve let go more and just let Sophie direct because she does a really great job. It’s just once I get an idea in my head, I have to see it all the way through. Again, I should’ve just left it. I’m sure it was very beautiful.
Lisa Loeb visits "Saturday Night Live" in Fall of 1995
Photo by: Al Levine/NBCU Photo Bank/NBCUniversal via Getty Images via Getty Images
Loeb followed up the success of "Do You Sleep?" with the more raucous, electric guitar-fronted "Taffy"—an intentional artistic statement meant to keep the flawed "folk artist" characterizations at bay. With her first two music videos being completely devoid of her band and only fleeting images of an acoustic guitar making it into the final cut of "Do You Sleep?," Loeb was adamant that her band and her electric guitar would both get prominent placement in the "Taffy" music video. She carried this through on the late-night TV promo run for "Taffy" as well, cranking up a fuzzed-out vintage Gibson Les Paul Junior for her appearances on The Tonight Show with Jay Leno and Late Night with Conan O’Brien in early 1996.
Lisa Loeb: I didn’t want to be too reactive after the success of "Stay," but I also didn’t just want to be pushed into the "acoustic" corner. I didn’t want to be seen as a folk artist at all. My music sounded like a band and I felt like the lead singer of my band; just like some of my favorite male music artists like David Bowie or Elvis Costello. However, during that period, if a female artist went by just her name, most people assumed you were a folk artist. That’s why I wanted to make sure my band name was included on everything and why I wanted to be seen and heard playing guitar. I realized early on that if you want people to know something about you, you have to show them.
While Tails was largely considered a commercial and critical success, Loeb still occasionally experienced the seemingly inescapable (especially for artists who are female) cliché of comparison in some reviews of her album. One critic referred to her hit single "Do You Sleep?" as "a polite version of Alanis Morissette’s ‘You Oughta Know'" and another mused that "perhaps America is in search of a female Hootie." When asked about these sentiments 25 years later, Loeb charmingly takes it all in silver-lined stride.
Lisa Loeb: During that time, there seemed to be a lot of comparisons between me and artists like Alanis Morissette and Liz Phair. A handful of the female singer-songwriters at the time were being very direct in their songwriting, which was a great, strong viewpoint that wasn’t always there before with other female songwriters. I felt like my strong point was trying to write about situations from multiple angles. I wasn’t trying to be polite, just cerebral and communicative. Still neurotic, but in a craftier way. As far as Hootie, those guys are so nice and I feel like I might have played golf with them once at some VH1 thing. The thing I like about that comparison is that Hootie was very popular; people really loved their music and bought a lot of it.
I just feel like my music, with the exception of maybe something like "I Do" later on, was such a different thing. I always put a lot of thought and energy into having variety in my songwriting, arrangements and instrumentation. I try to steer clear of formulaic pop songwriting. I think it’s just the blessing-curse of being on the radio. I wasn’t such an indie rocker that I was angry about being on the radio—I was very happy to be on the radio—but I was aware that there could be a backlash once you’ve been on pop radio. On the other hand, it’s great problem to have for millions of people to have heard your music. It can just be kind of weird to be pegged for something that doesn’t accurately describe you.
In the 25 years since Tails was released, many of the album’s tracks can still be found in Loeb’s present-day setlists and in her audience’s shouted-out requests. But although the songs themselves have remained active in her ever-expanding repertoire, the specific recordings on her major-label debut are still moment-in-time snapshots capturing an incredibly important career milestone in the early days of her prolific and ongoing career.
Lisa Loeb: When I listen back to Tails, I still feel connected to that same "me" from 25 years ago. I hear somebody who is trying to do her best. I had taken so many voice lessons to better understand how to sing the songs I had written and I was so connected to them during the recording process. I also hear a lot of confidence and hope at the same time. There’s a bit of that freshman attitude of trying your hardest and not being afraid of letting that show; which should always be there. I’m still invested in every song, every performance, every video, every choice in the artwork. It meant a lot back then because I cared about it so much and I still do. Even now, I still make records the same way, just a little quicker.
After her first big steps into the mainstream with "Stay" and Tails, Loeb has maintained an impressively consistent pop culture profile with more Top 20 hits ("I Do"), more soundtrack appearances (“All Day” from The Rugrats Movie), her own reality show (#1 Single), a flurry of television appearances ("The Nanny," "Gossip Girl," "Community," "Fuller House"), animated voice-overs (Spider-Man: The New Animated Series, Special Agent Oso), film work (House on Haunted Hill, Fright Night, Hot Tub Time Machine 2), and more. However, her top priority remains writing songs, performing concerts, and recording albums. This trio of activities has expanded to include children’s music in recent years, including her celebrated 2016 album Feel What U Feel, which won a GRAMMY for Best Children’s Album. Continually blending and balancing both (often overlapping) audiences, Loeb released her newest "grownup" album, A Simple Trick to Happiness, earlier this year.
Lisa Loeb: With A Simple Trick to Happiness, I’ve been able to co-write and collaborate in ways that allowed me to come up with something very personal and the songs have proven themselves to connect me to others. People really seem to relate to these songs and they seem to provide people with a lot of comfort. Like with the music video we did for "This Is My Life," it captures the craftiness and thoughtfulness that we have to have each day to puzzle our lives together. We’re so careful and we’re working so hard, but everything might change in the blink of an eye, and then we have to be right back at it again. If you look at the whole album, there’s an understanding that life can be difficult but also that there is a way to reframe things.
As a songwriter, I didn’t want to be one of those grown-ups who didn’t know what to write about once they weren’t writing about love and heartbreak as a twenty-something. I’ve always strived to tap into what I’m going through in the present moments. Honestly, making A Simple Trick to Happiness still felt a little like it did when I made Tails 25 years ago: It’s a new record, I want people to hear it, and I feel like the songs might really mean something to people.