1. Music

Lisa Loeb, headlining St. Pete Pride, talks nostalgia for 'Stay' and staying true to herself

Somewhere in storage, in a box or a trunk or a drive out of sight, Lisa Loeb has everything. All her old merch, every interview, as many TV clips as she could get her hands on.

"When we put out records, we made sure we got boxes of cassingles and point-of-purchase posters and all this stuff," the singer-songwriter said by phone from Los Angeles recently. "We were really good about cataloguing all the video appearances. So I have all that stuff. I have old costumes, dresses, wardrobe and puppets from videos. You name it, if it's a piece of nostalgia, I have it."

It's a good thing Loeb likes looking back, because this year, she has done a lot of it. This is the 25th anniversary of Reality Bites, the landmark Gen-X film whose soundtrack propelled Loeb's Stay (I Missed You) into the stratosphere. She has done her best to keep up with all the tributes and retrospectives, including a cast reunion at this year's Tribeca Film Festival, where she hopped on stage to sing Stay.

GUIDE TO PRIDE: St. Pete Pride's Parties, parades and more

"For the actors and Ben Stiller and the producers, they probably don't think about Reality Bites all the time," said Loeb, 51. "It's like the centerpiece of my career, in most people's eyes. Fans have a lot of other songs they love. But I understand that's a highlight, that a lot of people know that song. I end up talking about Stay, like we're doing now, and Reality Bites, all the time. I talk about it whenever I'm on stage. But I'm happy to talk about it, and happy to talk about the time. I'm also nostalgic in a way for it.

"But I also see people's current connection to it," she added. "To me, it still feels current, just like a lot of the songs I listened to when I was a kid."

Stay's staying power is part of what has kept Loeb in the public eye for 25 years, including a free concert Friday in Straub Park as part of St. Pete Pride.

Loeb, whose iconic cat eye glasses and baby-doll dresses made her the crush of many a '90s boy and girl ("I do hear that from women"), might not be the first name that comes to mind for a headliner for one of the East Coast's largest LGBTQ Pride fests. But she understands why her music resonates with LGBTQ fans.

"I think the Pride circuit picks up on the fact that one of my values — and I say this in a lot of my songs, and my music, my eyewear line, everything — is it's really about being yourself, being proud of who you are, finding yourself, being yourself."

That's part of what got Loeb through the media crush that followed Stay in the '90s. In the beginning, she often felt reduced to her dress and glasses, offended by how often it came up in interviews. But then she realized that she, too, felt that way about her heroes' fashion choices — Elvis Costello's glasses, the Beatles' mop-tops and suits, the bold looks favored by Elton John, David Bowie and Freddie Mercury.

"I realized I'm lucky to have something people can recognize me for," she said. "And hopefully that'll be the gateway to my music."

It ended up being killer branding. In addition to her eyewear line, she's an actor, a children's book author and a cooking show host. She has developed a coffee line and founded a summer camp for underprivileged children. On the day she called the Times, she had already mastered her next album, recorded voice-over for an animated series and written a song for the Amazon series If You Give a Mouse a Cookie.

What all her projects have in common, she says, is that "they all come from what I'm really interested in." That includes her booming second career in children's music. In 2018 she won her first Grammy for the kids' album Feel What U Feel, and she even sprinkles children's songs into her grownup shows.

Loeb's own kids, ages 9 and 7, are coming with her to St. Pete Pride. In fact, they're turning the trip into a five-day family trip, staying at a friend's beach house and plotting outings to museums, attractions and the festival itself. Loeb has long had an affinity for Tampa Bay — she fondly remembers playing a free Earth Day concert at the Florida Aquarium in 1998 — and has wanted to vacation here for years.

At St. Pete Pride, she'll play Stay, of course, but she also wants fans to request songs on Facebook, Twitter and Instagram. As nostalgic as she can be, she's still guided by the independent creative spirit that, 25 years ago, led to Stay.

"Pride parades are about celebrating people and who they are," she said. "Sometimes it's a personal fight to be able to be yourself — the fight against others so that you can hopefully come out on the other end as yourself. As somebody who's continually growing, things aren't always perfect, and hopefully we're always growing. That's in my music, and that's in my attitude."

Contact Jay Cridlin at or (727) 893-8336. Follow @JayCridlin.

If you go

St. Pete Pride concerts

Lisa Loeb headlines Friday at North Straub Park in St. Petersburg. Divine AF and Jennifer Real also perform. Free general admission, $50 for VIP. Gates open at 6 p.m.