"You'll Lose a Good Thing," Freddy Fender (1976)

A Mexican-American's country-esque take on an R&B waltz

Peak: #1 on the country chart (#32 on the Hot 100)
Streams: 768,000

Freddy Fender holds a distinct place in both pop and country music history. Born Baldemar Huerta, he was a Mexican-American singer who got his start singing Spanish-language versions of Elvis Presley and Harry Belafonte songs, briefly served in the Marine Corps, and eventually transitioned to singing rock songs in English. That’s around the time he legally changed his name to Freddy Fender. Soon after, he got sent to jail for marijuana possession, spent three years behind Louisiana bars, got pardoned by the Louisiana governor, and then moved to Texas, where he worked as a mechanic and played music on the weekends.