Eberly stayed with Jimmy Dorsey and would be a fixture with the orchestra until drafted into the service late in 1943.

In the early 1940s the Jimmy Dorsey Orchestra scored a string of hits featuring Eberly and Helen O'Connell, with Eberly singing a slow, romantic baritone version of songs such as "Amapola" and "Tangerine", followed by a lighter, up-tempo reprise by O'Connell.

In 1953, Eberly and Helen O'Connell headlined a summer replacement program for Perry Como's CBS television show.

[5] Eberly was married to Florine Callahan from January 23, 1940 until his death in 1981; the couple had three children, Robert Jr., Kathy and Rene.

Robert Jr. went on to sing professionally and although he was talented, he never achieved the popularity of his father which was due, in part, to the changing times and the diminishing nightclub scene.