Much of the record—co-produced by Freund and Sejo Navajas (Smoke Season’s Gabrielle Wortman, Vintage Trouble)—is devastatingly raw. The primarily acoustic arrangements are livened up with some spectacular drumming from Matt Johnson (St. Vincent, Jeff Buckley) and Michael Jerome (Toadies, John Cale, Blind Boys of Alabama), pedal and lap steel from Ben Peeler (Dawes, Shelby Lynne, Father John Misty), keys from Rami Jaffe (Foo Fighters, Ryan Adams) and Chris Joyner (Sara Bareilles, Rickie Lee Jones) and violin from Jessy Greene (Wilco, The Jayhawks). But even with all these studio heavyweights on call, Freund is front and center on the record, singing and playing an eclectic mix of instruments including guitar, mandolin, ukulele, synth and his signature upright bass.

Ben Harper, who produced Freund’s 2008 record Collapsible Plans, lends his vocals to “Abandoning the Ship” and supplies steel guitar to ethereal closing track, “Dream On (Believe in Yourself).” Grammy-winning mixer Jim Scott, known for his work with Tom Petty and the Heartbreakers, Wilco, Ron Sexmsith, Alejandro Escovedo, Lucinda Williams and many more, steps in for several sterling moments as well, leaving his sonic stamp on title song “East of Lincoln”, dreamy standout “Homer Simpson’s Clouds (Day of the Locust)” and dusky saloon romper “Poached Eggs.”

In many ways, Freund’s entire life and career have been leading up to this moment. He’s spent much of his time traversing genres, melding whatever sounds have happened to catch his whimsy with his unmistakable, earthbound songwriting. Back in high school, Freund played bass in the jazz ensemble and performed in productions such as Swing. A few years later, he enjoyed a brief stint in the off-Broadway scene and took classes at Columbia University in New York, later transferring to Pitzer College in Claremont, Calif., but when music came knocking again, Freund answered.

His very first album was 1992’s Pleasure and Pain, a duo set with Ben Harper. For the next five years, he also toured and recorded with The Silos before releasing North American Long Weekend, his 1998 solo debut on Mercury Records. Moving ahead into the new millenium, Freund churned out several additional records while also assisting with projects from Mandy Moore, Rachael Yamagata, Graham Parker and other notable artists. From a handful of EPs to his 2007 kids record Hug Trees and 2011’s The Edge of Venice to his appearance playing alongside Parker in 2012 Judd Apatow comedy This is 40, Freund’s career has been a dynamic affair, and that includes plenty of work in film and TV.

His songs have been featured on series such as Better Things, Parenthood and One Tree Hill, and for his latest television project, forthcoming Amazon show Pete The Cat, Freund has co-written, sung and played songs with Elvis Costello, KT Tunstall, Dave Matthews and Diana Krall, and has also co-written the show’s theme song with creator Swampy Marsh (Phineas and Ferb). Costello takes lead vocals on each episode’s opening theme with Freund handling backing vocals and most of the instruments. Freund also co-wrote and sings the show’s end-credits song, “Go Pete Go.” All 14 episodes of the animated series are scheduled for release this September.

East of Lincoln builds on Freund’s legacy while pushing beyond his comfort zone. “Angelus” is a groovy, organ-doused opener, and “Freezer Burn” a vulnerable mid-tempo affair reflecting on personal flaws in the wake of a breakup. “I was running on hope and fumes,” he sings. And where “London Bound Lady” is feathery and sweet, “Broke Down Jubilee” is gutting and mournful, glimmering with tears and silver-lined strings.

Freund’s new record is a potent reminder that life is measured not just bEast of Lincolnhow we choose to grow from our failures.

East of Lincoln is out Sept. 7 on Surf Road Records.