“People writing songs about AI is much better than AI writing songs about people.”

Paul Dempsey (Credit: Ashley Ludkin)

Ramona Was A Waitress, one of the most-loved solo songs recorded by Paul Dempsey, has officially gone Gold.
The song was released in 2009 and features on Dempsey’s debut solo record, Everything Is True, which was recorded between the two Something For Kate albums, Desert Lights (2006) and Leave Your Soul To Science (2012).
Upon its release, Dempsey commented that the song was about a conversation between a man and a robot waitress – the eponymous Ramona.
“Ramona Was A Waitress… It’s an unusual song,” he said. “It’s about a guy arguing with an artificial-intelligence robot waitress about mortality. Sort of an unusual subject for a pop song, but that’s just what I was thinking about as I scrawled the lyrics. Artificial intelligence and conscious robots arguing about the meaning of life.”
A mainstay of Dempsey’s solo sets – including his Shotgun Karaoke shows – and played at Fanning Dempsey National Park shows (his team-up with Bernard Fanning), we’re not surprised to see Ramona Was A Waitress go Gold. It’s one of the great modern Australian songs, after all.
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Reacting to the song going Gold, Dempsey shared a photo of himself holding the physical Gold record and wrote: “Back in 2008, I wrote a song about Artificial intelligence & look what turned up on my doorstep this week! Ramona Was a Gold Record!”
He continued, “Endless thanks to the dream team at Winterman & Goldstein & @emimusicau & @raykurzweil for the inspiration.
“People writing songs about AI is much better than AI writing songs about people.”
Dempsey returned with Shotgun Karaoke Vol. II in October, twelve years after the release of the original, classic Shotgun Karaoke.
Featuring covers of songs by Cher, R.E.M., Max Q, Don Henley, and many others, Dempsey challenged himself to sing each track in their original key and just perform songs he loves. He then took the album on the road for huge shows across the country.
The most recent Something For Kate album, The Modern Medieval, was released in 2020.