Jesse Winchester's final album coming Sept. 16 on Appleseed Recordings

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When the Southern singer-songwriter Jesse Winchester passed away on April 11, 2014, a few weeks shy of his 70th birthday, he left behind a legacy of distinctively insightful, gentle, frequently humorous songs about everyday people and their lives that became hits for other performers while he painstakingly crafted new classics to share.

Appleseed Recordings is honored to announce the September 16, 2014, release of Winchester’s final studio album, A Reasonable Amount of Trouble, written and recorded while he was in remission from the cancer that eventually returned and claimed him.

Although never a household name, Jesse was versatile enough to write pop, country and R&B hits for the likes ofNicolette Larson (“Rhumba Girl”), the Weather Girls(“Well-a-Wiggy”), Michael Martin Murphey (“I’m Gonna Miss You Girl), and even had his own Top 40 hit with “Say What” in 1981. His songs were also covered by Tom Rush, Jerry Jeff Walker, George Strait, Gary Allan, Patti Page, Elvis Costello, Jimmy Buffett, Joan Baez, Anne Murray, Reba McEntire, The Everly Brothers, Wynonna Judd, New Grass Revival, Fairport Convention, Tim Hardin, Emmylou Harris, Ronnie Hawkins, Ted Hawkins, Iain Matthews, Brewer & Shipley, Raffi, Wilson Pickett, and many more.

He recorded ten studio albums and several live releases, and was nominated for Best Country Male Vocalistat the Juno Awards of 1990. He also earned the Lifetime Achievement Award from the American Society of Composers, Authors and Publishers (ASCAP) in 2007. This fall he will be posthumously inducted into the Memphis Music Hall of Fame.

The new CD was produced by Mac McAnally, who also plays lead guitar (and has performed both functions for Jimmy Buffett, among others, for years), and features nine new Winchester originals and three lovingly chosen cover versions. Jesse plays acoustic guitar and keyboard and sings in his uniquely weightless tenor; there’s an attuned rhythm section, and guest appearances by “newgrass” country Grammy winner Jerry Douglas on lap steel and legendary saxophonist Jim Horn, among others.

Despite, or because of, his initial brush with death, Jesse still managed to write typically moving songs of life’s transient pleasures (“All That We Have Is Now”), tongue-in-cheek rockers (“Never Forget to Boogie”), and his uneasy peace with his — and everyone’s — eventual fate (the heartwrenching “Just So Much,” which closes the CD). Never maudlin, A Reasonable Amount of Trouble is tinged with his awareness of mortality but not a drop of self-pity. There’s Jesse’s humor, insight, tenderness, and even new versions of the sweet oldies he enjoyed so much (“Rhythm of the Rain,” “Devil or Angel,” and “Whispering Bells”).

The new CD, his second release for Appleseed Recordings, follows 2009’s Love Filling Station, which represented a career renaissance for Winchester as a recording artist and performer. The disc was a critical hit, and his performance of the album’s Sham-A-Ling-Dong-Ding,” a tender modern “oldie” about teenage love, on longtime fan Elvis Costello’s Sundance cable series Spectacle, wrung tears from fellow guest Neko Case, the popular country and alt.rock musician. The video of his performance, Neko’s tears, and Elvis’s reaction, “That’s it, Jesse, show’s over. You’ve finished me off!” was shown on the Today Show website and more than a hundred other online sites and became an instant YouTube classic.

Winchester, a self-described “gentleman of leisure” for the preceding decade, undertook an active touring schedule after Love Filling Station’s release, abruptly halted in June 2011 by a diagnosis of cancer of the esophagus. After surgery and related treatments, Jesse was pronounced cancer-free a few months later and, as his strength slowly returned, he started work on new songs for what became A Reasonable Amount of Trouble (the title borrowed from a Sam Spade quote from The Maltese Falcon). During his illness and recovery, another big-name Winchester fan, Jimmy Buffett, organized an all-star tribute CD named Quiet About It (a Winchester song title that summarized his creative modus operandi) featuring Buffett, Costello,James Taylor, Lucinda Williams, Rosanne Cash and other stars.

Shockingly, in February 2014, the dormant cancer was found in his bladder, this time without a cure, and Jesse spent most of his remaining months at home in Charlottesville, Va., before his death on April 11.

Many of his musical colleagues weighed in with their sense of appreciation and loss.

Bob Dylan was already on record as saying, “You can’t talk about the best songwriters and not include him.”Joan Baez wrote, “Thank you, Jesse Winchester. You will be missed.” From Jerry Douglas: “Godspeed to gentle soul and precious friend, Jesse Winchester.” And from Winchester’s Appleseed labelmate, Jonathan Edwards: “I’m so grateful for the opportunity he gave all of us to visit the environment he gently and invitingly created on stage, no matter the size or shape of the venue; to come into his world of genteel Southern charm and dry, incisive wit and stay for a while. The world is a better place having seen the precious colors he painted it with and the soulful intellect he brought to its presentation.” In his liner notes to A Reasonable Amount of TroubleJimmy Buffett writes, “In my way of thinking, Jesse may no longer reside in the world of matter, but his energy sure as hell does. It is timeless and eternal and will be with us always from Montreal to Memphis, to those red skies off toward New Orleans” (referring to a line from one of Jesse’s earliest and best-known songs, “Biloxi”).

A particular surprise was a retweet by Jerry Seinfeld to his 2.3 million Twitter followers of an April 11 tweet from Albert Brooks, the witheringly funny actor, writer, and director, which read “R.I.P Jesse Winchester. If you watch this and you’re not moved you’re dead” and provided a link to Jesse’s show-stopping Spectacleperformance.

Appleseed president Jim Musselman posted, “Jesse was a beautiful human being and one of the most wonderful artists that I have had the honor to work with. We had just finished recording a new CD with him called A Reasonable Amount of Trouble and he was very excited about the songs on the album. Jesse recorded a new song about life called “All That We Have Is Now” about living life fully, and also a beautiful song about facing death titled “Just So Much” that I cannot listen to without getting tears in my eyes. He showed such courage facing death and was strong throughout. We all can learn a lot from him in many ways . . . I am heartbroken over the loss of this remarkable musician.”

Perhaps Elvis Costello said it best: “The word that comes to mind is ‘grace.’”