Montgomery collaborated with George Jones on 1963's "We Must Have Been Out of Our Minds", which reached number three on the Billboard Hot Country Songs chart.

She also collaborated with Gene Pitney during the sixties on the top 20 single "Baby Ain't That Fine" (1965).

Both United Artists and Musicor issued several solo studio albums and singles by Montgomery during the sixties also.

In 1970, Montgomery teamed up with Charlie Louvin to record the top 20 country single "Something to Brag About".

Her second self-titled studio LP spawned a cover of "Angel of the Morning", which reached number 22 on the Billboard country chart.