- Famous for writing the western song, "Back in the Saddle Again." The song came about when Whitley was awakened early one morning by a telephone call from his bosses at RKO Pictures, who wanted him to write a song for a new western he was to be starting that day. Explaining the call to his wife, he said, "Well, I'm back in the saddle again." She said that would be a good title for the song, he agreed, sat down and wrote the song in just a few minutes. He performed it later that day while shooting the movie. Cowboy star Gene Autry later heard the song, thought it would be perfect for him, got together with Whitley and rewrote it slightly, then used it in his next movie, and it became his signature song.
- In 1937 he approached the Gibson Guitar Co. with a design for a custom guitar he wanted made for himself. The company was so taken with the design it became the popular Gibson SJ200. Ray's original guitar is on display in the Country Music Hall of Fame in Nashville, TN.
- Managed the Sons of the Pioneers in 1937 and helped negotiate their contract with Columbia Pictures. However, he refused to sign the contract himself since he believed Columbia was not giving the Pioneers as much as they deserved.
- Held a variety of jobs before he became a singer/cowboy actor, one of which was as a steelworker helping to construct the Empire State Building in New York City.
- Once turned down the opportunity to manage Hank Williams due to other commitments.
- Frontman of The Six Bar Cowboys.
- Was at one time the manager of cowboy actor Jimmy Wakely.
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