'Stay'-ing power: Lisa Loeb reflects on her 25 years in the public eye

Incredibly, singer-songwriter Lisa Loeb is about to release her 15th album (yes, 15th!), A Simple Trick to Happiness, on her own record label, Furious Rose. It’s a full-circle happy moment for the 51-year-old mother of two, who first came to fame when her song “Stay (I Missed You)” landed in the zeitgeist-capturing '90s film Reality Bites and established her as the first independent, unsigned artist to go to No. 1 on the Billboard Hot 100. She was in fact the only independent, unsigned artist in Billboard history to achieve that feat until 2013, when Macklemore & Ryan Lewis did it with “Thrift Shop.”

“It was great to have an independent start,” Loeb tells Yahoo Entertainment. “It was nice to have that security and that sense of creative control, that I was going to be able to continue on until now.”

Loeb got the Reality Bites opportunity while she was living in New York after college, hanging with an artsy circle of friends that included then-rising young actor Ethan Hawke, who passed “Stay” along to the producers of the movie. When the song ended up on the hot soundtrack, which also featured U2, Lenny Kravitz, Squeeze, and the Knack, Loeb decided not to sign a record deal at the time, instead keeping “Stay” indie and just licensing the track to RCA. (She eventually signed with Geffen for her 1995 album, Tails.) But she still convinced RCA to make a music video for the future hit.

“I think the record company let us make a video because Ethan Hawke was directing it, because he was a movie star,” Loeb laughs. “But really, the great part about the video was that he decided to shoot it all in one take.” Unlike some one-shot music videos that are actually several attempts cleverly edited together, “Stay” really was done in one tracking shot.

“We shot it a million times. … There's so many outtakes,” says Loeb. “I also had a bone to pick with Ethan, I really wanted my band [Nine Stories] to be in the video. … I was like, ‘People need to see that I really play guitar! This is really important to me, my guitar playing!’ I studied it for years, and I'm super into it. They needed to see my band, because I'm not a girl, I'm a person with a band.” Hawke agreed to film a handful of takes with the band, but “the artistic expression of just me singing without my guitar told the story so much better than me and my band and my guitar, that I just went with the stronger creative vision,” Loeb explains. And the rest was history.

The video had a massive impact, becoming an MTV alternative-rock smash that catapulted the “Stay” to No. 1 and Loeb to instant fame. What truly made the clip so iconic was Loeb’s look, notably her Betsey Johnson-designed little black dress (which, it turns out, was actually dark green) and her sexy-secretary cat-eye spectacles. It’s a style that people still emulate now, especially with '90s style back in vogue. “I was at Target the other day, right before Halloween, and I was like, ‘Here's a Halloween costume for me and anyone else in the '90s!’ It was that little dress, short with a little bit of puffed sleeve and a scoop neck,” Loeb chuckles.

It’s a timeless look she’s still rocking in her new video from A Simple Trick to Happiness, “Skeleton,” as well. “It’s that thing where you get to be you,” Loeb explains. “It fits lots of different body types. You get to be sexy and fun. It's for you. Other people enjoy it too, but you're on the go and you put on your Docs or your other shoes, and you're just ready to go.”

While the public reaction to her appearance and the “Stay” video surprised or even bothered Loeb at first, back in the 1990s, she came to be grateful for the fact that so many young girls — particularly girls who wear glasses — saw her as a fashion role model. “At the beginning, when I was starting to get played on the radio and all that stuff and commercial success was happening, I didn't want to talk about my glasses,” she admits. “I wanted to talk about my music and my guitar playing and all this other stuff, which I thought was more musician-y.” But, she noticed, “People stopped me all the time after a while and said, ‘Oh my gosh, I feel comfortable wearing my glasses, because you wear yours.’ That still happens today. People stop me at airports and grocery stores and they say, ‘My little girl will wear her glasses, because you wear glasses.’

“I realized along the way that there was such a connection, and it's such a hobby of mine as well, finding cool glasses,” Loeb continues. “That discussion was really important to me, to see how it had changed some kid's life. … Instead of being put off by the glasses, I was like, ‘That's actually my people. These are my people.’” Loeb even eventually decided to launch her own eyewear line, with each frame named after one of her songs. There is, of course, an iconic “Stay” model.

Still, there were times in those early crazy days when Loeb was genuinely uncomfortable with how she was presented, like when one stylist dressed her up as a “waif” for a dark, Gothic photo shoot, but she learned from that experience and took those lessons into her long, largely independent career. “I was such a strong, business-minded [artist], super into writing music and performing music and knowing about the music business, and yet here I was in this picture before I had been really established, looking really waif-like. It was really negative. I [looked] very thin and very shy,” Loeb recalls ruefully. “That's not me. It's an interesting artistic expression, but that's what I remember a lot from those days … making sure I was presented in a way that felt like me, that looked like me, having that creative control over your presentation of [myself]. I think that's so important, whether you're a businessperson or an artist.”

Watch Lisa Loeb’s full Yahoo Entertainment interview below, in which she discusses A Simple Trick to Happiness, her love of cats and Hello Kitty, and her groundbreaking E! reality dating show Number 1 Single, Lilith Fair memories, and how she balances, motherhood, marriage, and music.

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