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Born on 22 May 1983 in Melbourne, Australia to Salvation Army parents, the second of four children, Darlow moved to Hong Kong at five years of age. He spent the next six years there attending Beacon Hill Primary School before returning to Melbourne to begin high school. Two years at Essendon Grammar were then followed by another move to Perth, Western Australia, where he attended Hollywood High School. After this, he moved back to Melbourne where he completed school at Strathmore High School.
Following on from high school, Darlow began a teaching degree at RMIT. During this time, he also worked in bars and pubs, including a two-year stint at Melbourne Hilton on the Park. Upon completion of his university studies, Darlow worked at three high schools and one primary school, teaching music. After two and a half years of full-time teaching, Darlow resigned to focus on writing music, recording and touring.
Darlow started playing the cornet at five years of age. With both of his parents being Salvation Army Officers, his first musical experiences were of watching the brass band at Hawthorn Salvation Army. He is said to have fallen in love with music from that moment on, determined to play in the band just like the men he watched each Sunday. He was given a cornet at five years of age, and started playing in a brass band at age seven. From there, he learned to play Beach Boys and Beatles songs. Darlow continued to play the trumpet throughout high school, along with classical guitar. It was also at this time that he started playing trumpet and saxophone in bands around Melbourne. Darlow is said to be proficient on the trumpet, trombone, saxophone, clarinet, didgeridoo, piano and guitar, as well as being a singer.
At nineteen years of age, he decided to start taking his guitar playing more seriously and began writing songs. After being introduced to and mentored by Melbourne gospel artist Paul Colman, Darlow began recording his first album, entitled Be with You, with indie producer David Carr. It was released under the name of his band at the time, The Darlow Show, in January, 2003. This album included crowd favourite track "Sorry", a song about his Aboriginal heritage which included a vocal part from AFL footballer David Wirrpanda. This was followed in 2005 by a live acoustic album called Underground, also released under The Darlow Show moniker. In 2008, Darlow released a third album called The Whole Earth Sings, this time under his own name. Total combined sales of physical copies of these albums exceeded 23,000.
In January, 2016, Darlow released the first single from his fifth album, "Solid Rock", a cover of the Goanna hit from 1982. Darlow enlisted the help of the song's author and original singer, Shane Howard, on vocals and recorded it as a duet. "Solid Rock" was added to radio stations all over Australia and New Zealand and was the most-played rock song on Australian radio in February, 2016. Similarly, the music video for the single went viral after radio station Triple M shared the video via Facebook, with over 200,000 people viewing it.
Darlow released their second single from the album, "Down Like Flies", in late May, 2016. This second single got solid radio play around Australia, with the supporting music video featuring well known Australian actor Matt Hetherington, his wife, TV personality Melissa Hetherington and TV and radio personality and author, Jane Gazzo.