It is inevitable that every account of Billie Holiday's life focuses on the prolonged addiction to drink and drugs that culminated in her premature death at the age of 44 on the 17th July, 1959. This compilation, however, is entitled "Happy Holiday" and thus attempts to concentrate on the upbeat side of her career.
Having said that, although many of the songs included here are upbeat musically, lyrically or both, Billie's voice is so plaintive and her phrasing and melodic invention so unique that even seemingly 'happy' songs often sound wistful and melancholic. Several songs whose lyrical content would seem to qualify them as 'happy' have been omitted simply because of Billie's delivery. Nevertheless, Billie handles the bitter-sweet comedy of numbers such as "A Fine Romance", "Let's Call The Whole Thing Off" and "My Sweet Hunk O' Trash" (in a duet with Louis Armstrong) with great style and humour, justifying record producer and talent scout John Hammond's description of her: "She was not a blues singer, but she sang popular songs in a manner that made them completely her own. She had an uncanny ear, an excellent memory for lyrics, and she sang with an exquisite sense of phrasing. She always loved Armstrong's sound and it is not too much to say that she sang the way he played horn. Further, she was absolutely beautiful, with a look and a bearing that were, indeed, Lady-like and never deserted her, even in the degraded final years."