"Do You Sleep?", Lisa Loeb & Nine Stories (1995)

Her entire first album is so great, y'all

Peak: #18 on the Hot 100
Streams: 2.2 million

Technically, Lisa Loeb isn’t a one-hit wonder. While it’s true her entire legacy as a pop star has now been boiled down to “Stay (I Missed You)”, she in fact sent two other singles into the top 20. Perhaps you remember “I Do,” the Replacements-adjacent toe-tapper that hit #17 in 1997. That was the lead single …