Whiskey was born and raised in the small community of Indulkana in the APY Lands to a family very involved in the arts, and she grew up around the art centre. As she grew older, she said that painting there was "a good way to keep busy and spend time with my family".[2]
She has developed a unique style which includes pop stars in bright colours; her favourite musicians Dolly Parton, Tina Turner, Michael Jackson and Cher (whom she often listens to as she paints) are often featured in her work. Whiskey says:[3]
I like to listen to rock music and Tina Turner, and I paint with really strong colours, I put in lots of the special details, and everyone likes it. I paint strong stories too, paintings about heaven and Jesus, and sometimes Mintabie and paintings about my country Indulkana. Sometimes my paintings tell hard stories, but my paintings are always colourful and painting them makes me happy.
— Kaylene Whiskey
Whiskey refers to these idols as her kungkas, which means "woman", most often "young woman", in the Yankunytjatjara language.[4] She has said:[5]
'It's one of my dreams for Dolly to come and visit me in Indulkana, I love to listen to her music while I paint: "9 to 5", "Coat of many colours", "Jolene", and my number one, "Islands in the stream" with Kenny Rogers. I often think, "If Dolly came to visit, what would she do? What would she say? And what would she be wearing?".
Whiskey was a finalist of the Archibald Prize in 2020 for her self-portrait (in which she is accompanied by Dolly Parton); this work is entitled: "Dolly visits Indulkana".[5]
2022: Iwantja Rock n Roll at the Fort Gansevoort gallery in New York, along with the work of Vincent Namatjira and Tiger Yaltangki. Included in the exhibition is her work Kungkas in Hollywood (2021), in which the artist is portrayed in a fantastical scene with Beyoncé and Dolly Parton.[4]
2022: Whiskey partnered with knitwear bran WAH WAH to produce vibrant knits including 20 motifs from her artworks.[11] These include cockatoos, boomerangs alongside her idols Cher, Dolly Parton and Wonder Woman.[12]
2024: Whiskey is a participant in the 2024 Biennale of Sydney at White Bay Power Station.[13] It features her installation 'Kaylene TV' which is a walk in television set filled with female pop icons, including black Wonder Woman, which appropriates pop culture.[14]