Listen to When You're Smiling online. When You're Smiling is an English language song and is sung by Bing Crosby and Judy Garland. When You're Smiling, 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 2:42. Download English songs online from JioSaavn.