Settling in Nashville, Tennessee, Trask was signed to Dot Records in 1968 where her cover of "Hold What You've Got" made the US country chart.

Trask's music continued making the US country charts and she toured alongside performer Roy Clark in several Las Vegas engagements.

She reached her peak commercial success in the middle seventies with four top 20 country songs: "Say When", "It's a Man's World", "When I Get My Hands on You" and "Lean It All on Me".

[11] She started received vocal lessons from Melbourne instructor Jack White,[12] who helped her audition for the local Channel Seven television competition called Swallow's Parade.

She often performed on a program called In Melbourne Tonight (IMT) but ended after it was rumored that Trask's father would sponsor the show through his furniture business.

She then obtained her own radio program on the ABC network called Diana Trask Sings, which was heard by American promoter Lee Gordon.

Trask recalled Miller reprimanding her when her vocal style "got too swingy" and on occasion telling her to leave the session until "you feel like doing it my way".

[28] Among her early Columbia singles was the 1961 pop ballad "Long Ago Last Summer", which Billboard called "highly spinnable".

[34] Columbia then issued Trask's first full-length eponymous album in March 1961 featuring arrangements by Glenn Osser and 12 covers of American pop standards.

[35] A second full-length LP was released in November 1961 titled Diana Trask on TV featuring Miller's "Sing Along Chorus" in the background.

[42] After an Australian entertainment friend suggested she return to her home country to restart her career, Trask and her husband moved back in 1963.

[52] Despite never hearing of the Grand Ole Opry radio show,[53] Trask was invited to attend and was instantly drawn to the music.

Despite her initial reluctance about recording the song (it had only been six years since Cline was killed in a plane crash),[64] it rose into the top 40 of the US and Canadian country charts in 1969.

[69] Her first Davis-produced LP was 1972's Diana Trask Sings About Loving[70] which featured the US top 40 country singles "We've Got to Work It Out Between Us" and "It Meant Nothing to Me".

[71] Halsey booked her to tour alongside Roy Clark and the pair worked together for several years,[72] beginning with a sold-out, four week stint at The Frontier hotel in Las Vegas.

[62] Trask then paired up with producer Jim Foglesong, who found her a song he believed would be her biggest hit called "Oh Boy".

[65] Trask claimed that "Oh Boy" was not a bigger because it did not receive enough promotion due to a record label "changeover", calling it one of her "biggest professional disappointments".

[83] Trask signed with the Kari label in 1980[84] and the company issued her final singles to make the US country chart: "This Must Be My Ship" and "Stirrin' Up Feelings".

[56] During this period, Trask embarked on a three-month tour in Australia[85] and recorded a new studio album with the Hammard label titled One Day at a Time.

[30] In the US, Trask spent time focusing on songwriting, receiving assistance from Nashville composition team Jerry Foster and Bill Rice.

[87] According to Trask, she never received proper credit for the song's composition and after the Foster-Rice team sold their company to a larger songwriting conglomerate, her career was "left to drift".

[98] According to her official website, the album was derived from original audio tapes of The Di Trask Show and were digitally remastered.

[100] In her memoir, Trask discussed her feelings toward Frank Sinatra: "There was no doubt I was heavily attracted to him and times were sweet between us but we both knew we were going nowhere together.

[107] As newlyweds, the couple lived in the California coastal cities of Huntington Beach (and later San Diego) and Ewen worked for the Anheuser-Busch beer company.

[4][117][113] Trask was inspired in her early career by traditional pop and jazz singers such as Rosemary Clooney and Doris Day.

[118] When she transitioned into country music, Trask listened to the records of singers like George Jones, Waylon Jennings, Willie Nelson, Dolly Parton and Patsy Cline.

Trask stated that Cline and Parton were her favorite female country artists because they sang with a less "nasal" delivery than their contemporaries.

[21] Greg Adams of the website AllMusic described Trask's 1974 Lean It All on Me album as being similar in sound to that of a "young Barbara Mandrell".

[121] In describing her vocal delivery, writers Mary A. Bufwack and Robert K. Oermann called Trask a "power-voiced" singer who could "stun listeners with her fiery technique".

[123][124] Fellow Australian singer, Helen Reddy, credited Trask as an early influence in her book The Woman I Am, writing, "When I had seen her perform in person, I thought she had not only had a lovely voice, but also a good choice of material, great stage presence, and she carried herself like a star.