3 One-Hit Wonders Who Won Grammy Awards for Their Hit Tracks

When we remember our favorite one-hit wonders—you know, those artists who saw their songs rocket up the charts but who never quite saw that same success again—we often think about memorable but goofy offerings. Songs about things like purple people eaters or letting the dogs out.

Videos by American Songwriter

But there are some one-hit wonder tracks that have gone on to earn some prestige and even take home major awards. That’s just what we wanted to highlight below. Indeed, these are three one-hit wonders that won Grammy Awards for their hit tracks.

“I Try” by Macy Gray from ‘On How Life Is’ (1999)

With a distinct voice and a feeling that she both knows where you’ve been and remains hopeful about where you can go, Macy Gray entered our lives in the late 1990s with the song “I Try” and she’s been here ever since. Gray’s hit single won her the Grammy Award for Best Female Pop Vocal Performance at the 2001 show. It was also nominated for two more—Record of the Year and Song of the Year. The song is about hardship, about how difficult love and living are. And it was Gray’s elastic, yet relatable voice that made the whole thing perfect.

“Don’t Worry, Be Happy” by Bobby McFerrin from ‘Simple Pleasures’ (1988)

You know what’s a funny idea? A song about relaxing and being happy, also being a juggernaut at a cut-throat awards show. But that’s exactly what happened at the 1989 Grammy Awards. Bobby McFerrin took home the trophies for Song of the Year, Record of the Year, and Best Male Pop Vocal Performance. What a night! The simple, yet sublime offering is one of those tunes that anyone from any walk of life can get behind. And they did just that at the end of the 80s.

“Baby Got Back” by Sir Mix-A-Lot from ‘Mack Daddy’ (1992)

A song about butts—how could this track be actually significant? Well, that’s the genius of the Seattle rapper Sir Mix-A-Lot. He brought listeners in with booty cheeks but then also helped to subvert the beauty standards of the day. Indeed, that was his intention. He was tired of seeing what he thought were overly slender people on magazine covers. It was time to put some curves in the forefront. So, he wrote a song about it. And it not only earned Mix a Grammy, but it went No. 1 on the Hot 100!

Photo by Lorne Thomson/Redferns