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Wilson released his album Gentle Spirit on Bella Union on August 8, 2011 in the UK & Europe and on September 13, 2011 in the US. The album debuted at number 15 on the UK Indie Chart and was awarded the #4 spot on Mojo's 2011 Best Albums of the Year list.[1] Gentle Spirit features many special guests including Barry Goldberg, Chris Robinson, Gary Louris, Andy Cabic, Otto Hauser, Josh Grange, Gary Mallaber, Z Berg, Adam McDougall, Johnathan Rice, among others. Jonathan was named Uncut Magazine's 2011 "New Artist of the Year".[2]

In April 2012, Wilson released "Pity Trials and Tomorrow's Child", a limited edition vinyl EP on Bella Union for Record Store Day 2012. American Songwriter Magazine named it, "Five Things To Look For On Record Store Day".[3] One of the album's three tracks, a cover of George Harrison's "Isn't It A Pity", includes guest vocals by Graham Nash.

Wilson also completed a solo album titled Frankie Ray in 2007. The record was never officially released.

In August 2012, Jonathan was featured as a guest of Move Me Brightly, a tribute to Jerry Garcia in honor of his 70th birthday. The event was held at Bob Weir's TRI Studios in Marin County, California and featured other guests and musicians including Bob Weir, Phil Lesh, Donna Jean Godchaux, Jeff Chimenti, and many others. In June 2012, Jonathan and his band were invited by Tom Petty & The Heartbreakers to support them on their 2012 European tour, which included 2 sold out nights at Royal Albert Hall.

In the fall of 2011, Wilson was invited by Roy Harper as a special guest at Royal Festival Hall as part of Harper's sold out 70th birthday celebration. Wilson also toured with Wilco in the fall of 2011 for 15 shows across the UK & Europe. In July 2011 Wilson performed and collaborated with Jackson Browne and Dawes on a mini tour throughout Spain. Wilson performed at the 2011 benefit concert for Musicians United for Safe Energy at Shoreline Amphitheater joining Crosby, Stills & Nash, Jackson Browne, Bonnie Raitt, John Hall,The Doobie Brothers, Jason Mraz, Tom Morello, Kitaro, Sweet Honey In The Rock and others. Wilson was joined onstage by Jackson Browne and Graham Nash to perform his song "Gentle Spirit". Wilson also joined Crosby, Stills & Nash, Jackson Browne, Bonnie Raitt and others for the concert's finale, "Teach Your Children".

In 2010 and 2011, Wilson collaborated with Erykah Badu in the studio on several songs, only one of which was officially released. Wilson also appeared as a special guest with Erykah Badu at her 2011 Coachella performance.

In October 2013, Wilson released his second album, Fanfare, on Downtown Records and Bella Union. The album debuted at #8 on the UK Indie Chart, #50 on the UK Overall Chart, #18 in the Norway Overall Chart and #49 in the Netherlands in its first week. Uncut Magazine and Rolling Stone Germany named Fanfare its Album of the Month the month of its release. The album features contributions from David Crosby, Graham Nash, Jackson Browne, Mike Campbell, Benmont Tench, Father John Misty, Taylor Goldsmith (Dawes) and Patrick Sansone (Wilco). The album also features Wilson's band, including Jason Borger, Omar Velasco, Richard Gowen and Dan Horne. British folk legend Roy Harper wrote the lyrics to the song "New Mexico".