Lisa Loeb
Getty Images/Theo Wargo
June 01, 2017 05:40 PM

For some people, Lisa Loeb will eternally remain the cat-eye glasses-wearing crush they first heard in Reality Bites in 1994. But Loeb has resolutely refused to keep still in the intervening years, taking detours into film and television acting and lately, children’s music. She’s currently in New York for a residency at the famed Cafe Carlyle, and PEOPLE caught up to her to see how she’s been “Stay”-ing busy. (Sorry.)

How did you get involved with the Carlyle?

I’d never imagined that I’d be going there. I’d seen Betty Buckley and people like that do their shows there and over the past year two different people approached me, people who had seen my shows recently. And it’s not the American songbook — though every now and again I might play “Life Is Just a Bowl of Cherries” or “I’m Always Chasing Rainbows” — but I tell a lot of stories and it’s gotten to the point where I mostly just play with my guitar and me singing, and the Carlyle is the perfect place for that. Every one of my sets is different from night to night, and I do rely a lot on the audience’s preferences.

I play all kinds of places — huge family festivals, outdoor theaters, rock clubs — and what I really love the most are seated theaters or places like the Carlyle. They’re listening rooms. You really do feel the audience there.

You have two Office alumni on your most recent album, Feel What U Feel.

There are a lot of musical people from The Office! I was talking to Kate Flannery about doing something recently, actually. I met all of them on the set years ago. My husband had done some work with them, and we visited the set, and everybody’s just a friend or a friend of a friend, and we all got along instantly. And when I met Craig Robinson, we shook hands, and we just started singing to each other. I’d see him around Los Angeles, and we started talking about doing something together, but I didn’t know what. We were writing one song called “Feel What U Feel,” which is a disco-funk jam, and I thought, “This would be really fun for Craig and I to sing together.” But I realized that it was more of an outro, so I was looking for another song, and I thought of “It’s All Right to Cry,” from Free to Be You and Me, which is one of my favorite records, and it was just a perfect match for him.

And then I was recording a song called “Wanna Do Day,” about having one of those days where you have to do all this junk that you don’t want to do. It’s from a kid’s point of view, but a grown-up can definitely identify. It needed some kind of bubbling-under sound, so we decided to put banjo on there. I’d had Steve Martin play banjo on another kid’s record, and he and Ed Helms are kind of the only two banjo players I know.

So you’re just rolling through the checklist of famous comedians who are also banjo players.

Well, they’re both really great players! Also, not to be hippy-dippy about it, there’s an energy about them. Someone like Ed is so kind and he really fits the feeling of the album. I really love the tone of comedy from the 1970s — The Carol Burnett Show, Sesame Street, Steve Martin’s old comedy routines, the Muppets — things that are really for all ages; they err on the side of being for grownups, but they’re appropriate for kids, as opposed to something like Shrek, which is for kids but has a little extra for the grownups. And I loved that and wanted to do something like that, and it turned out that was making kid’s music.

And you also have your own eyewear line going, right?

Yes, about seven years ago, I partnered with Classique Eyewear, a company in San Diego.

When your glasses became such a talking point early in your career, did you ever think you’d be making your own?

I didn’t. I’m a huge Elton John fan, and I knew he had a bunch of custom glasses with fur and windshield wipers, and I thought, “That’s cool.” To have an opportunity to make my own is really amazing. I actually shied away from the glasses when I was first starting out because I wanted people to talk about my music and my guitar playing and my songwriting, and for that to be put on a shelf while people are talking about my cat-eye glasses… I was kind of offended. Now, looking back, I realized I had a really unique opportunity. There are so many musicians out there, and it’s always important no matter what you’re doing to feel confident and secure in what you do and to keep doing that, but if there are different little selling points that people catch on to, if it’s a good match, you should embrace those things.

You were the first unsigned artist to have a No. 1 hit. We’re seeing more artists these days circumvent the major-label system or the traditional route to music stardom — what was that like for you 20+ years ago without the Internet or any of the modern tools we take for granted?

Well, I had a team. I had a manager, I had a song on a soundtrack. My friend Ethan Hawke passed the song along to Ben Stiller, and that’s an amazing connection. But what’s really unusual is that they decided to put the song into the movie. You can have all the friends you want, which is a huge stepping stone, but those people still have to like what you’re doing enough to do something with it. And I gave them the rights to promote it as a single, then a radio station in Houston started playing it as a single on their own, which was also unusual … so I was lucky in that a lot of different things lined up for me. You are able to get the word out these days without spending a lot of money, but there’s still something very calculated about the music industry. It still takes a lot of strategic know-how.

You’re active with a lot of charities, as well — what have you been doing lately?

Well, I’m working with the Muddy Puddle Project, which is run by a woman named Cindy Campbell. Her son Ty had cancer when he was a kid, and he always said that when he got better, he wanted to be able to jump in muddy puddles. But he didn’t get better. And so his mother wanted to try and pull something positive out of this, and so the muddy puddle is a symbol for kids — and adults — to always try to enjoy life and take these small moments and not put them off until later. And this year, she was able to partner with Peppa Pig, which is a British cartoon, to get more exposure. You can do your own muddy puddle parties, or welly walks — which is where you wear those big boots and stop through the rain and mud — and they provide resources for people to hold these events to raise awareness for childhood cancer, but also to help raise funds for cancer research. And also that whole other message of taking these small moments and not putting things off.

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