From the editor

You might know her from her debut hit "Stay (I Missed You),” or from her other top-20 singles or certified gold albums. Or you might know her from her children’s music; she won the Grammy Award for Best Children's Music Album in 2018. You might even know her from her cameo in the final episode of Gossip Girl. But safe to say, you know Lisa Loeb. Get to know her better in this 2006 interview, written as she was embarking on a journey into reality TV with her series #1 Single.

Mik Moore, President, Heeb Media

Mik Moore, President, Heeb Media

Lisa Loeb, Re-Branded

From 2006

Lisa Loeb, Re-Branded

By Arye Dworken · Photography by PHOTOGRAPH BY: Ilona Lieberman · October 21, 2026

Originally published in This article was originally published in HEEB #10, Spring 2006.

I'm here to interview Lisa Loeb, but nearly an hour after I've arrived, I've met her stylist, stylist's husband and child, hairdresser and make-up artist, publicist and publicist's assistant, but not Lisa Loeb. In her Chelsea apartment in Manhattan, I'm witnessing the cogs and the gears of reinvention in motion, turning and cranking. Hair spray is being sprayed, sexy dresses are being presented and, for the most part, rejected ("too slutty"), sticks of lip gloss are drawn from back pockets and applied with the swiftness of a cosmetic paramedic. Right now, I am sitting in the midst of Hurricane Lisa, and the forecast only suggests a slight chance of interviewing.

When I'm finally introduced to the folk singer, I make a sympathetic remark about how hard it seems to be back in the saddle again.

Loeb looks at me sharply behind her signature geek glasses and responds, "Back? I never stopped."

And, in truth, she hasn't. When her label sent me her new greatest hits compilation The Very Best of Lisa Loeb, I was surprised to discover that the majority of the songs on the album had been recorded subsequent to the 1994 release of Reality Bites. Long after "Stay (I Missed You)," her first hit single, surprised the nation by being number one on the pop charts (without even the support of a label), Loeb continued touring, recording and hair spraying all the while. Who knew?

But we're not just here to discuss her music. We're here to discuss her scripted/reality show #1 Single. The show's premise: Loeb is single for the first time in twelve years (she's had two consecutive six-year relationships, the latter with Dweezil Zappa) and her biological clock is ticking. Loudly. Like a good Jewish girl, she's looking to settle down and have children. In fact, during the first episode, when her mom speaks about grandchildren, Loeb gets unrepentantly teary. It's a moving moment, and in retrospect, you almost feel guilty for having never set her up with that decent-looking doctor you know from the gym (and he's a dermatologist, so that means he wouldn't have crazy hours).

"So, what kind of guy are you looking for?" I ask.

"Seriously?" she replies.

" I know a lot of people," I say. "You never know."

"A good guy. A funny guy."

"An Ethan Hawke or a Ben Stiller?"

"Um...right now? A Ben Stiller."

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