After a stint with the local blues band Killing Floor, Widdowson formed theRainjackets a trio who smart combination of rock and catchy pop captured in 1990 on the self released cassetteInside Out received local radio airplay and led to gigs opening for such name artists as Peter Case, Toad the Wet Sprocket, Deacon Blue, Subdudes and Dave Mason.

After the Rainjackets, Widdowson played solo acoustic gigs eventually hooking up with bassist John Guion and as the acoustic oriented Simon Widdowson Group issued a cassette in 1991 called Grandma Jumping Bull.

Adding drummer Mike Olszewski and keyboardist Pat Weeks the group spent 2 days in a Minneapolis Studio in May 1992 with recording engineer Rob Genadek and recorded 15 songs. The album was released under the nameSpearfish.

In 1993 Widdowson moved to Santa Fe New Mexico and embarked upon a several year period of relentless touring across the US performing 250 - 300 shows a year and on October 8th 1994 he recorded a live acoustic session at Groovy Studios in Santa Fe resulting in the solo album Looking For Delilah.

Widdowson continued to tour and while based in Santa Fe he recorded two more albums; Going Home Undressed as a trio with bassist Justin Bransford and drummer Andy Primm in 1996 and then a solo acoustic album in 1998 titledWeather Vane.

In 1999 Widdowson moved to Portland Oregon and opened the Are You Listening? Recording Studio and Art Space where he began recording and producing albums for other artists including; Decemberists, Pete Krebs, Hindi Guns, Papillon and many more. In 2002 he recorded his 7th album, titled Sweeper, featuring the talents of Ezra Holbrookon drums and Aaron Masonek on bass. Playing occasional live shows around the Northwest and continuing his work as an engineer/producer Widdowson in 2004 joined forces with Jason Bedard (King Black Acid) on drums, Kelly Simmons (Man of the Year) on bass and James Beaton (Everclear) on keyboards and the group recorded the album Frame. The album was completed in 2005 when Widdowson left Portland and returned to New Mexico.

In 2005 Widdowson left the US after almost 20 years and built a recording studio in Cork Ireland where he recorded and produced several Irish acts including Arm The Elderly, The Driven and Box Camera.

In 2007 He relocated to Lyon France and after working on albums for French artists Karimouche and Zen Zila he recorded his 9th album titled Loss of Innocence with Jason Bedard on drums, Pierre Granjean on bass andChristian Fradin on keyboards. In 2011 25 years after he left, Widdowson returned home to England and spent a year playing approximately 75 shows around the North of England before in 2012 deciding to return to France.

Over the last 25 years Widdowson has performed over 1500 concerts in the UK, USA, Ireland and France and recorded and released 9 albums of original music. In October 2013 these albums are finally being made available digitally for the first time, remastered and with never before released bonus tracks.