Swift began performing and singing in Quaker churches around the age of fourteen and began writing and recording his material at home not long after. In 2001, Swift moved to Southern California to pursue his solo recording career. He recorded Walking Without Effort but, unhappy with the record, shelved it.
In 2002-03 Swift recorded The Novelist, selling home-made copies at shows in and around Los Angeles. Later in the year he went on to release a small pressing of "properly manufactured" versions via Velvet Blue Music. In 2004, Swift combined The Novelist and Walking Without Effort to create the double-disc The Richard Swift Collection Vol. 1. He signed to indie label Secretly Canadian, who then re-released the Collection in 2005.
After touring in the US and Europe and releasing half a dozen 45s/EPs, UK major label Polydor signed Swift, and yet again the double disc was re-released in hopes of introducing Swift to the UK. In 2007, Polydor/Secretly Canadian issued his proper follow-up "Dressed Up For the Letdown". Fans and critics praised the record as Swift's greatest work to date. Later in the year Swift met Wilco-frontman Jeff Tweedy during a taping of the BBC program "Later...with Jools Holland". Tweedy asked Swift to support Wilco on their Sky Blue Sky US tour. During the tour Tweedy invited Swift to record at their Loft in Chicago, IL. In October 2007, Swift started his 4th LP at the Wilco Loft. The year ended with Richard canceling a string of November shows with friends Cold War Kids due to a wrist injury.
In late February 2008 the Secretly Canadian website announced the future release of a double EP named "Richard Swift As Onasis". This album was released on 04/08/08. In August of 2008, Swift released an EP entitled "Ground Trouble Jaw" as a digital download. In April of 2009, Secretly Canadian released "The Atlantic Ocean" which saw the return of Swift's pop-centric song writing.