Last night, Lisa Loeb stepped out of a cab in front of Highline Ballroom with an orange guitar case slung across her shoulder, her hair pulled into a low ponytail, and her eyes hidden behind her iconic black-framed glasses. She is petite with a somewhat soft voice, and speaks thoughtfully and intelligently, like the smart, quiet girl in your college literature seminar. In 1994, Loeb was the first artist to have a number one single in the United States while not signed to a recording contract. Almost 20 years later, she is still plugging away and making music, and in January she released a new record, No Fairy Tale. We walked to Chelsea Market before her show at Highline, and caught up over coffee about what it means to be '90s female pop icon, eyewear, children's music, and having to play "Stay (I Missed You)" over and over, and over.