Songfacts®:

• Originally titled "The Biggest Fool Of All," this country-pop ballad finds Brenda Lee struggling with the news that her boyfriend is a serial cheater and wondering how many other girls he's fooled. The single did well for Lee, peaking at #3 on the Hot 100, but more importantly it gave an up-and-coming country singer her big break.
  
  The song was written by Kathryn R. Fulton for Sure-Fire Music, a publishing company owned by the country duo The Wilburn Brothers. They also ran a talent agency, and one of their latest finds was a Kentucky-born singer they met at the Grand Ole Opry: Loretta Lynn. Hoping to land her a record deal, they brought a demo of her singing "The Biggest Fool Of All" to Owen Bradley, the vice president of Decca Records' Nashville division. Bradley was also Lee's producer and he insisted she sing the tune instead. The Wilburn Brothers agreed - in exchange for Lynn getting a contract. Two years later, Lynn released her debut album on Decca, Loretta Lynn Sings, with Bradley as her producer.
• This was released as the second single from Lee's seventh studio album, Brenda, That's All, following "You Can Depend On Me," which was originally recorded by Louis Armstrong.
• This was also a Top 40 hit in the UK. Lee became popular there after appearing on the British teenage music program Oh Boy! in 1959 and taking the #3 spot on the pop chart with "Sweet Nothin's" in 1960.
• Loretta Lynn did end up recording this after all. Her version was included on her sophomore album, Before I'm Over You (1964), produced by Owen Bradley. It was also covered by Johnny Tillotson, Connie Smith, and Marie Osmond.