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Early life and career
Hollingsworth was born in Maryland on March 2, 1968. He attended Towson State University where he majored in music, with a focus on jazz piano. While attending college, Kyle played in the Baltimore-based psychedelic rock band, Black Friday.
After moving to Boulder, Colorado, he eventually joined The String Cheese Incident, an American jamband from Boulder. He has written a number of songs for the band, by himself and with collaborators such as Robert Hunter.
When not on tour with String Cheese Incident, Kyle tours with his band, the Kyle Hollingsworth Band. He has also toured under the names Kyle Hollingsworth & Friends and 3 Foot Icon, the latter featuring Kyle, Speech (of Arrested Development), and Chief Xcel (Blackalicious).
Kyle released his first solo album, Never Odd or Even, in 2004. The album features saxophonist Joshua Redman and pedal steel player Robert Randolph. He toured in support of Never Odd or Even under the name Remarkable Elba Kramer.
In the spring of 2008, Hollingsworth toured briefly with the Fiery Furnaces as the band's second keyboard player.
His second album, Then There's Now, was released on September 15, 2009. The album features Dave Watts (of the Motet) on drums, Ryan Jalbert on Guitar, Garrett Sayers on bass, and Damien Hines and DJ Logic on turntables. It also features Liza Oxnard (of Zuba) and Alex Botwin (of Pnuma Trio).
In 2014, Kyle released his third album, Speed of Life.
In 2018, Kyle released his fourth album, 50.