The first awards show was held in 1977 with singer Pilita Corrales winning the Entertainer of the Year Award followed by Rico Puno and Celeste Legaspi in 1978 and 1979, respectively. In 2007, the Award was given to Regine Velasquez, who also received it in 2009. In the 2011 Aliw Awards, 19-year old International Singing Sensation Charice was the recipient, making her the youngest artist to be conferred such recognition.
Sarah Geronimo is the only female artist in the history to win all of the major awards from "Entertainer of The Year" in 2010, "Best Female in Major Concert" in 2012 and 2010, "Best in Collaboration" in 2011 and "Most Promising Female Entertainer" in 2003.
Aliw is the root word meaning "to entertain" in Tagalog.