Kid Dakota is the musical moniker of Darren Jackson. He started performing as "Kid Dakota and the Tumbleweeds" in 1998 while living in Providence, Rhode Island. The name was chosen in homage to his home state of South Dakota and also as a parody of Kid Rock. In the summer of 1999, Darren recorded the five songs that would appear on the So Pretty EP with long-time friend and producer, Alex Oana, at City Cabin (formerly Blackberry Way). Darren moved to Minneapolis, Minnesota that winter and self-released the So Pretty EP in the spring of 2000.

The EP caught the attention of Alan Sparhawk, singer and guitarist for the seminal slow-core band, Low and he offered to release the EP on his label, Chairkickers' Union under the condition that it be expanded into a full-length LP. The LP version of So Pretty was released in the spring of 2002 with three additional songs. In 2004 his second album, The West is the Future, was also released by Chairkickers. It was recorded live at Seedy Underbelly in Minneapolis, MN by Alex Oana and featured Zak Sally, the bassist from Low. A Winner's Shadow, was released on March 11, 2008 on Graveface Records, who would release Kid Dakota's next album, Listen to the Crows as They Take Flight, in October 2011.