Listen to A Pretty Girl Milking A Cow online. A Pretty Girl Milking A Cow is an English language song and is sung by Bing Crosby and Judy Garland. A Pretty Girl Milking A Cow, from the album Bing Crosby With Judy Garland And Al Jolson (Digitally Remastered), was released in the year 2011. The duration of the song is 2:57. Download English songs online from JioSaavn.