Lisa Loeb Reflects on Her Favorite TV Spots & 30th Anniversary of Iconic Song ‘Stay’

It was 30 years ago when Lisa Loeb made history as the first Billboard number-one single for an artist without a recording contract. The song was “Stay (I Missed You),” which became synonymous with the 1994 romantic dramedy Reality Bites.

Since then Loeb and her iconic tune have been fun fixtures throughout television, movies, and even commercials. She most recently even appeared on That ‘90s Show during a dream sequence with Callie Haverda’s Leia Forman in the star’s signature look. Coming off the cameo and release of her new collaborative album with The Hollow Trees, we thought it would be fun to reminisce with the Grammy-winnner about some of her favorite TV guest spots.

Congrats on the new music. I read there are some inspirations for “That’s What It’s All About” in particular taken from TV shows like The Little Rascals and The Three Stooges. Tell me a bit about that. 

It’s a really nostalgic album. There are songs we chose based on all the songs I listened to with my parents and grandparents. I loved them growing up. They were grown-up songs, but there is a sense of whimsy where the lyrics and music have a sense of storytelling and play that appeals to all ages. I wanted to put these on a record. Together with Greg [Mcilvaine] of the members of The Hollow Trees wrote a song.

My aunt had a song from the early 1940s or 1950s that had never been recorded before. My cousin Danny said, “You know she has this song called, ‘I Want to Shake Hands With The Man On The Moon.’ It was such a perfect addition to the record. It tied together the feeling of nostalgia and actual family relations as well as the feeling of sitting down and listening to music from a different time. It’s funny when we were asked about the song “Taken It While The Taken’s Good,” which is our original song with Greg. Images we were choosing are what you’d see in The Three Stooges. It’s a very visual song. You can imagine all the scenes happening in an old black-and-white movie or technicolor movie. It tells a story like almost a mini-movie.

Ben Stiller, Lisa Loeb, Winona Ryder, Janeane Garofalo and Ethan Hawke attend “Reality Bites” 25th Anniversary – 2019 Tribeca Film Festival (Theo Wargo/Getty Images)

A lot of people were excited to see you on That ‘90s Show. This tied perfectly with the 30th anniversary of Stay. What do you make of the song’s staying power? 

Lisa Loeb: We’re celebrating 30 years of the song. It has been such a powerful song in my career as a singer-songwriter with a band that had been playing for many years and all through high school and college and a few years into living in New York City. That song launched my big commercial career. I had a really great following and things were moving well, but that launched my commercial career.

A big part of that was the music video. People really related to that one-take video that Ethan Hawke directed. They were able to hear the song and lyrics. As much as it is a nostalgic song, I find that when I’m playing concerts pretty frequently people really relate to it now. There is a timelessness about it. I’ve been lucky to have a song like that. It leads people to listen to other songs of mine from newer albums. You know you have a big success when people parody your music like they’ve done in Hot Tub Time Machine 2, TV commercials.

The GEICO commercial! 

The GEICO commercial! You know you have an iconic song when you’re able to have fun with it. Still when I play it live or when they hear it on the radio they do get that emotional connection to the song. I love doing both of those things. When I was a kid, I loved it when Paul Simon was on Saturday Night Live or when Steve Martin, who is a comedian, would play music. He was also an actor. I love that music-comedy connection. I love being part of that. It’s a song that stands on its own, which I appreciate. I have had a lot of fun with the song on TV shows.

(L to R) Callie Haverda as Leia, Lisa Loeb as Herself in episode 202 of That ’90s Show. Cr. Patrick Wymore/Netflix © 2024

What are some of your favorite appearances? 

I did love That ‘90s Show. I couldn’t believe they completely recreated the look of the set and the young actress in the show had my outfit on. I had my Betsey Johnson on as well. It was really fun to have the present and future combined into one. I’ve really made a lot of cameos on TV shows. Everything from early on in The Nanny when I told Fran Drescher that I wanted her to bring Bobbi Fleckman from This Is Spinal Tap on her show and wanted to be the assistant. So I’ve had the experience of being on a sitcom early on through Community, About a Boy, A.P. Bio, and Teachers. There are so many.

It was fun to see you show up on Gossip Girl including the series finale. What do you remember about that? 

I played “myself.” It was in two episodes. I was in the finale where I played Rufus’s girlfriend as Lisa Loeb. It’s always fun to do that and work with writers, produce directors, and come up with the version of Lisa Loeb that is still something I can stand behind that fits well into the world of their storyline and their show. In Community for example I played, not me, but another singer-songwriter without glasses. That was funny too. I love connecting with people from so many generations. When I was on Fuller House, so many younger kids said they wanted to hear the newer song I played in the episode. They come to my concerts. Their parents are fans or even grandparents. It’s really cool way to connect with people multi-generationally. For Gossip Girl, I remember because the finale was so over-the-top because there was a wedding. We did spend quite a bit of time sitting on sofas, hanging out and talking to each other, waiting for Blake Lively’s character to be dressed in her full wedding regalia.

You a lot of times do play Lisa Loeb on these shows. Was there a show where you were like, “I want to play someone different?”

I did that a bit on Community. I studied acting growing up and all through college. Music seemed to take the lead over and over again. It took all my energy, so I put my focus on that. Being an actor was something I always really loved. So much so that at the beginning, I didn’t want to play myself as a cameo on a show. I’d rather just be an actor being on a show playing a nurse, receptionist, or best friend. Little by little I realized how much fun my fans are having with it.

I realized that for myself it was also really fun. It’s fun being on set. It’s like a field trip. I get to go behind the scenes. I get to see how the directors work, producers, and writers. I get to see how the costumes are made and be in the professional world of Hollywood. And often especially over the last 10 years, I do get to do some acting. Even when I’m playing myself there will be a couple of scenes that we’re doing, so it’s great practice for me as an actor. It touches so many points about getting to live a very rich life. Getting to connect with my fans in a whole different way and bring in younger fans who see me on their popular TV shows and continue to make new music.

Have you ever turned down a TV show that wanted to use you for a part or your music? 

I have a couple of times. I’m just going to leave it at that. I still have great opportunities that come to me. I say yes to the ones I feel confident and excited about. There have been a couple of situations where I do read the script where the Lisa Loeb they have written form goes out of bounds like when I was on About A Boy. I thought  I was being mean to a little kid in the TV show I thought as much as I like to have fun and go outside my own character to fit into a character in the show, that’s too far out of bounds. I worked with the writers to come up with something that was still funny and edgy but not that far out of bounds.

Lisa Loeb and The Hallow Trees (Photo Credit: Frances Iacuzzi)

What was the moment you felt Reality Bites and the song was getting big?

I think it was right in the middle of everything. The movie came out, the song was going up the charts, and a radio station in Houston called KRBE decided to play the song because they liked it from the soundtrack. It wasn’t the promoted single from the record company. They chose the song. We were flown down to Houston to do a big promotion. Hearing the song on the radio in a limousine in Houston driving to the radio station and in the context of other big singers like Mariah Carey. It really drove the point home hearing my song with the wraparound from the radio station. It was a different level than hearing the cheers from a full CBGB club in New York City. It was a whole different level.

Here 30 years later, have you seen the movie recently? 

That’s a good question. I don’t know the last time I watched it. It has been a while. I really should watch it again. Recently I was on tour and when I was in Indianapolis, I went to the Kurt Vonnegut Museum. I always liked him and bought a book I hadn’t read since high school. I read it again and it was a completely different experience for me. I thought I should start a book club where you read books and return to them with the same group of people every 20 years or something. That would be great to do with Reality Bites. Some of the movies we watched when we were younger and continue to return to them and see them with a different lens. That would be fun. That’s why it’s fun to watch reruns or shows I didn’t watch whether it was because I was busy or in college or a little old or young. I started watching a little Golden Girls, which is really funny, or Seinfeld, Friends. To watch them now is fun.

You also did reality TV. Would that do something you did again? 

I would produce reality TV. I had a show called Number One Single on E! And I was one of the producers I would only do a reality-based TV show if I’m a producer on it because I need to see every single thing, every edit before it’s sent to a network. There are a lot of different ways you can tell a story with documented footage or footage that has been coaxed into a story. I don’t want to ruin reality TV for anyone, but I knew the story I wanted to go in and tell and wanted to make sure we hit those marks. On the E! show, I wanted to tell the story of a person in my late 30s and what it felt like to date and think about what kind of life I had.

Earlier than that I had a Food Network show called Dweezil & Lisa with Dweezil Zappa, which had elements of real life, but it was very produced. We knew what we wanted to tell as part of our life as touring musicians and families. We learned a lot about the different chefs we learned from along the way. I prefer to be a producer in reality TV if I do it again because it is time-consuming. I have so much on my plate that I’d rather focus on rather than have a camera on me all the time.

What’s a show you want to be on that you haven’t? 

I wanted to be on Curb Your Enthusiasm. I love improvising, and it’s one of my favorite shows. I was talking to Ted Danson about that the other day on the blue carpet at an event for Oceana. I would like to be on that. You got me on the spot. I should know this. I always tell actors or anyone else to think about where they want to be so they can get there. I would like to be in a drama. I would do another horror movie, but I’d love to do drama. A really good comedic drama. Or even just a straight drama. One of my favorite movies is Ordinary People. So to be in a drama-drama would be amazing.