Lisa Loeb Looks Back at Her Multifaceted Career and Ongoing Education as a Guitarist and Songwriter

Back in 1994, Lisa Loeb burst onto the pop scene with “Stay (I Missed You),” featured in the movie Reality Bites. Loeb’s song, built on her colorful chord voicings and R&B-style grooves on a Taylor guitar, became a touchstone of ’90s music, a companion to countless romantics mulling over breakups, and a major hit—earning Loeb a Grammy nomination and the distinction of being the first unsigned artist to top the Billboard Hot 100.

Loeb, who was in her mid-20s at the time, was one of those overnight successes many years in the making. She’d been learning, performing, and writing music since she was a kid growing up in Dallas; released two albums with her college friend Elizabeth Mitchell, as Liz and Lisa; written music for theater; and founded the New York City–based band Nine Stories. And along the way she’d grown into a versatile guitarist, studying styles from folk to rock to jazz standards, both privately and in a summer session at Berklee College of Music.

All these experiences have fed into the multifaceted career that Loeb has built in the three decades since “Stay”—as a musician, film/TV/voice actor, theater writer and composer, SiriusXM radio host, and entrepreneur, with her own line of eyewear. As a singer-songwriter, Loeb has continued to make smart, sophisticated pop rock, most recently with the 2020 album A Simple Trick to Happiness. And like her college bandmate Elizabeth Mitchell, Loeb became a prolific kids’ music artist, winning a Grammy for her 2018 release Feel What U Feel. The 2017 not-for-kids-only album Lullaby Girl showcases Loeb as a gifted vocalist interpreting standards, show tunes, Motown, and soft rock hits. Her newest album, That’s What It’s All About, is a family-music collaboration with the folk/Americana band the Hollow Trees, celebrating songs recalled from childhood and adding some new co-written originals.

In the fall I connected with Loeb, based in Los Angeles, for a conversation on her path—and ongoing education—as a guitarist and songwriter.

I’m curious how you learned guitar. Was it from lessons, songbooks, records? 

I started as a pianist, and I came from a family where to learn an instrument, you took lessons. My interest in guitar started at my all-girls school. They had classical guitar as part of the curriculum in seventh or maybe eighth grade, and it was full of folk songs on guitar, like “Stewball” and “Edelweiss.” 

My friend Alma Doll showed me a few things at summer camp on an acoustic guitar. She started teaching me “Stairway to Heaven,” and then I took lessons from the same teacher she had: Mark Menza, who’s still a composer in Dallas, Texas. I learned a lot of theory, some jazz, and songs I liked at the time—David Bowie songs and the Police, like “Bring on the Night.” One of the first songs I played with some friends in a talent show was “Over the Hills and Far Away” by Led Zeppelin. I also tried to use sheet music books and learned to figure out songs by ear. I was already writing music a little bit, starting with piano when I was a kid, so I definitely continued with that as a young teen.

It sounds like you had a lot of tools and approaches to learn from.

Yeah. I was playing in a cover band in my senior year of high school, and we would figure out songs in different ways. And then I took guitar lessons off and on through the years. After college, I went to Berklee summer school because my little brother had gone there, and I wanted to have that opportunity to woodshed and really focus on guitar playing. I played a lot growing up, but I have so many different interests that I felt like I needed time to dig in more deeply.

Also, I will mention that my brother was a really amazing classical pianist; even as a young child, he was doing tons of competitions. On one hand, there’s this feeling of needing to be the best, to be a prodigy and to know every chord and all the theory behind everything. And I have to say, although that’s a great drive to be better and have more knowledge and skill, also the great thing with playing guitar is you can do so much with so little. That’s also something to embrace. We can have both of those things at the same time. 

When I was first really writing a lot of songs with lyrics, I was at an acting school in London for the summer and borrowed a guitar, and two of the strings were missing. I wrote songs all summer! It was great. I just think that’s important, because sometimes you feel like you can’t do it at all if you can’t be amazing at it. You know, it’s the old thing: even with two or three chords you can play so many songs.

Many of the bands that inspired you as a teenager were more electric oriented, but the acoustic guitar became such a prominent part of your own sound. What pointed you in that direction? 

Yeah, a lot of the music I grew up listening to was more on the rock side. If there was acoustic guitar, it was more about the arrangement, like [Elton John’s] “Someone Saved My Life Tonight” I think has a strummy acoustic guitar in the background when the song gets really emotional, or David Bowie liked to play around with folk rock on some of his earlier albums. The Cure might have acoustic guitar in there. 

The Police was mostly electric. I loved electric guitar. When I first started playing, because I had seen Andy Summers in some photos with a Peavey Backstage amp, I got one of those. That was a good size for a kid, as opposed to the huge [Roland] Jazz Chorus that I got later. I bought a Peavey electric guitar, which I quickly returned because it was too heavy for me. I ended up getting a reissued 1978 Stratocaster, which I loved. But for a five-foot-two person, carrying or wheeling around that Jazz Chorus amp and the Strat in one of those Fender hard cases, it was so, so heavy.

So little by little, as a shy person who wanted to quietly write songs in my room, and because of the heaviness of the equipment, I moved over to acoustics. You could hear it in your room, and it was much lighter and easier to transport. The acoustic goes well with my voice, which is on the quieter side, and then I did start falling in love more and more with the acoustic sound. 

There is also the feeling of playing acoustic guitar. It’s like playing drums—you actually can feel the instrument in a simpler way than the electric. It’s just you with your instrument. You don’t need an amplifier and a cable and whatever pedals you might use.

Your breakthrough song “Stay (I Missed You)” dates from your time studying at Berklee. That song has a really distinctive guitar part, capoed and fretted way up the neck with unusual voicings. Do you discover parts like that just by experimenting on the fingerboard, or through more of a theoretical sense of what you are going for?

It’s always a combination of things. I do like messing around to find guitar licks, patterns, chord progressions, and chord voicings that I like, and I might build an entire song around those at times. Or I might get to a place in a song where I want to say something melodically and lyrically, and I try to have a relationship of that with the guitar part that I’m writing. 

For “Stay,” though, it was specifically that I heard from somebody I knew at BMI Music that Daryl Hall, from Hall and Oates, might be looking for songs for a solo record. I’d never written a song for anyone else, but I thought, ooh, that would be so cool to write a classic ’70s Hall and Oates song that had an R&B groove. So that’s where I got the basic groove of the song and the chord progression—not the [opening] lick, but the groove. 

How did you find the pattern that takes you so high up the neck, all the way to the 16th fret?

Often I’ll start writing, and I’m in my room and it’s very quiet, so I’m writing songs that are too low for my voice. I end up using a capo to move it to a place that fits my voice better. 

With “Stay” it just was natural to look for an interesting guitar lick, hand in hand with the way the lyrics and the story were developing. The song ended up being an unusual structure, but it tells the story of the song. I think the structure tells the feeling of the song almost better than the lyrics do, if that makes sense. The song has a quiet, introspective beginning and ends in a similar way, after going through a lot of different emotions and feelings and mental struggles. 

How would you describe the structure of the song? It doesn’t really follow the conventions of verse, chorus, bridge, etc.

It’s like a book. The guitar lick and the walking-up-the-neck sound helps create the space to have a thought: “You say I only hear what I want to.” I’m kind of thinking about it as I walk up the neck. There’s another thought, and the walk-up again. And then I go into the meat of the story in my mind, which is the groove, and go back to the intro again, like I’m recapping.

It’s like the song has different little chapters where I keep starting over. That’s also how we think; as soon as we finally let the snow globe settle and we’re at peace for a minute, some other big thought comes to mind, and it’s like a new chapter again. 

Rather than repeating sections, the song is continually unfolding.

Exactly. It kind of unfolds and then folds back up again. 

Do you typically find a song’s guitar part at the same time you’re writing words or a melody?

It all happens in every way. I’ve made up complete songs and then needed to write lyrics for them. I’ve written lyrics and then wondered what that melody is, and found it. I’ve found chord progressions that I really like, and then I play around with melodies and certain words come up. I’ve wanted to write a song with a certain rhythm or a certain feel. . . So really it happens in all different ways. 

And if I ever feel like I’m getting stuck, it turns more into happy homework, where I’m like: I want to write a song that has very few words, or a really straightforward song that sounds like a cowboy song, or a song like some other artist’s song. That gives me a little goal. And then in the middle of it all, if you’re lucky, you just get inspired. You’re driving and you hear a melody with music in your head, and lyrics. There are ideas that just happen. Sometimes I’m spelling out chords on my tape recorder to make sure I know exactly what I’m hearing, and then the song develops from there.

In terms of guitars, you’ve played the same Taylor grand concert going all the way back to around 1990, right?

Yeah. My friend Liz Mitchell (who I had a band with in college called Liz and Lisa) and I went to New York City to make a demo with Jon Gordon, who was a guitar player with Suzanne Vega. Jon had this custom Taylor guitar that he had gotten at Matt Umanov Guitars [in New York City]. It was smaller than my guitar, it had the cutaway, and it was really beautiful. I ended up getting the exact same one he had, a 512c with gold tuners and a Florentine cutaway and a little bit thinner neck, and I still have it. 

Once “Stay” hit and I was touring more, I bought a non-custom version of the same guitar so that I could have a backup. I like that one too—it has a little bit of a wider neck—but I keep coming back to the same [custom] one. I have a bunch of guitars hanging on the walls, but the Taylor is just so comfortable and reliable and sounds really good. It works well for “Stay,” for sure, because I can play very high up the neck.

You’ve released a lot of kids’ music over the years, including your latest album, That’s What It’s All About, with the Hollow Trees. Has making music for kids and families taught you lessons about songwriting or music making in general? 

One hundred percent, because I feel more free in that place to play around with genres, and with things that might feel silly or too serious or even too heartfelt. Also, the further away you get from having radio hits, the more wide open things feel. 

As a songwriter, I’ve been working a long time on being able to tell stories that people understand. I’ve admired a lot of artists whose stories I did not understand—I understood the feeling of the song. But along the way, I’ve also learned I like to tell stories that people understand, and that especially becomes important when I’m playing live concerts.

Also, through collaborating more when making kids’ records, it’s important to communicate with each other as we write music. So that process has really folded back into my grown-up music, both collaborating more and thinking a little bit more about what’s important to me. What do I feel like writing about? What am I saying? That has really affected me. 

Do you look at writing or making music for kids as very different than making any other kind of music?

No. With the family-friendly music, it’s really important that there’s no lesser quality of chord progression or melody or lyric or attention to detail. The songs are written and recorded with the exact same quality as grown-up music will be. 

One thing is that when I play some of those kids’ songs live at my grown-up shows—you know, evening shows at grown-up locations—the grown-ups really like those songs. That’s what folk music is. I used to resist folk music because I felt like more of a rock ’n’ roll person, even though I was a girl with a guitar. But it’s really fun and satisfying to play those songs. The audience really enjoys them. 

On That’s What It’s All About and on some previous records, you interpret a lot of music you grew up with—folk songs, cowboy songs, standards. Do those old songs form a big part of your sensibility as a singer-songwriter?

It’s definitely a piece of it. My parents had that classic 1940s–’50s upbringing, with a lot of musical theater and standards. With those old songs, I always loved how whimsical the lyrics were and how visual they were, and I wanted to be able to make things like that.

I’m a nostalgic person, and when I hear a song, it’s not really just about the music, it’s about where I was and what I did. It’s what the sun looked like coming through the prism in my grandfather’s living room. It’s what we were eating, like the jellybeans out of the jar at my grandparents’ house, or the roses growing up the side of the house. It’s the smell of pancakes, and it’s Sunday morning and my dad is playing “Don’t Fence Me In” from a fake book.

I did a lullaby record and covered “Dream a Little Dream,” which is a song my dad really loved. To be inside those songs is kind of like being in a vintage store trying on old clothes—you feel like you’re there. It’s a full experience.

What She Plays

Lisa Loeb’s go-to guitar throughout her career has been a 1989 Taylor 512c built with custom specs for Matt Umanov Guitars in New York City. That Taylor has a Fishman undersaddle pickup that she runs through a Fishman Aura Spectrum DI; the company created a digital image for the Aura based on her Taylor’s acoustic sound. 

Loeb uses Shubb capos, sometimes way up the neck—as in live performances of “Sandalwood” (capo IX) and “Waiting for Wednesday” (capo IX or X). She uses medium Fender or Ernie Ball picks, and Ernie Ball Earthwood phosphor bronze medium light strings (.012–.054). —JPR

This article originally appeared in the March/April 2025 issue of Acoustic Guitar magazine.