The song was sung by Jack Jones the teenage son of Anne Jones the publican of the Glenrowan Inn (Victoria, Australia) while it was under siege by the Kelly Gang. The siege was broken by the Victorian Police on the morning of Monday June 28, 1880. Jack Jones died of injuries sustained during the police assault on the hotel.
Percy Grainger recorded an English language version on wax cylinder from Joseph Leaning of Lincolnshire in 1906, which has been digitised and can be heard online. In 1907, the Austrian ethnologist Rudolf Trebitsch used the same technology to record an Irish language version in County Kerry. Some time in the early 1900s, the famous uilleann piper Patsy Touhey was recorded playing a version, which is available on the Irish Traditional Music Archive.
It enjoyed a revival when an updated swing version sung by Irish-American singer/actress Judy Garland was featured in the 1940 film Little Nellie Kelly. The updated version is true to the original musical air, and incorporated original lyrics by MGM Musical Director Roger Edens, and featured Garland singing the song to George Murphy using some of the original Gaelic lyrics in the first chorus, which was true to the traditional air, before moving into an up-tempo swing version typical of the era.
The song was released as the B-side of the more popular Garland song It's A Great Day for the Irish by Decca Records in 1940. It became a popular song for Irish-Americans during St Patrick's Day celebrations. It remained a popular number for Garland throughout her career, and most notably she sang it live in its original Irish language version in July 1951 at her Theatre Royal concerts in Dublin, Ireland. A Dublin review stated: "Remember the song she sang in "Nellie Kelly" – "The Pretty Girl Milking Her Cow." Judy is providing herself with the Irish version – "Cailin Deas Cruidte na mBo" while in Ireland". Later in 1951, she included the song in her first record-breaking appearance at New York's Palace Theatre, although this time reverting to the new version that combined both English- and Irish-language lyrics. The song is also featured on Garland at the Grove on Capitol Records, recorded live in 1958 at the Coconut Grove in Hollywood. I always thought the song was written for Judy Garland. It was not, but she made it sound like it was!