"The Wayward Wind" is a country song written by Stanley Lebowsky (music) and Herb Newman (lyrics), and first recorded by American singer Gogi Grant in 1955, and released in 1956. Grant's version reached No. 1 on both the Cash Box charts, where it remained at No. 1 for five weeks, and the Billboard charts, remaining at No. 1 for six weeks, ending Elvis Presley's seven-week run at No. 1 with "Heartbreak Hotel". It remained in the top 10 for fifteen weeks, and was ranked as the No. 5 song for 1956 according to Billboard. It became a Gold record. Members of the Western Writers of America chose the song as one of the Top 100 Western songs of all time.

Myrtle Audrey Arinsberg, known professionally as Gogi Grant, was an American pop singer. She is best known for her No. 1 hit in 1956, "The Wayward Wind".