HerbJeffries
The song is "Space Cowboy" by Steve Miller Band. "You know you know where it's at."
Hank Snow, lyrics here: http://www.lyricstime.com/hank-snow-hawaiian-cowboy-lyrics.html
Roy Rogers
Selena Gomez?
I believe it was the Andrew sisters
Im not sure but it sounds like Johnny Tillotson
The song was performed by Harry Nilsson.
Cowboy
Chris LeDoux I'm pretty sure it was Porter Wagoner, but I am after the same answer.
Oklahoma country singer, Becky Hobbs.
I don't think he sang with any group. In the 20's he played a singing cowboy but his real voice wasn't used, it was dubbed over. If I remember correctly, he hated playing this singing cowboy.
The black hat that Merle Haggard famously wore is often referred to as a "cowboy hat" or specifically a "stetson" hat, which is a brand synonymous with cowboy hats in American culture. It became a signature part of his image, representing his connection to country music and the working-class roots he often sang about. The hat symbolized both his rugged persona and the themes of his music.