[2] Showalter has released eight studio albums—Leave Ruin (2009), Pope Killdragon (2010), Dark Shores (2012), Heal (2014), Hard Love (2017), Eraserland (2019), In Heaven (2021) and Miracle Focus (2024).

[2] Showalter spent his nights in hotels and on park benches with a borrowed guitar while working at an orthodox Jewish day school.

[2] Showalter's first album Leave Ruin was released in 2009 on the Pennsylvania label La Société Expéditionnaire[2] while touring and collaborating with Lou Rogai (Lewis & Clarke).

On Christmas Day in 2013, Showalter and his wife Sue were driving back to Philadelphia from Indiana when they hit a patch of ice and crashed into two semi-trucks.

The near-death experience gave Showalter a boldness during mixing sessions while creating Heal with John Congleton, just days after the crash.

Showalter has toured extensively in support of the album and opened for Jason Isbell, Iron and Wine, and Ryan Adams.

[8] On December 1, 2016, Timothy Showalter announced the fifth album from Strand of Oaks called Hard Love, which was released on February 17, 2017.

[11] In Pitchfork, Stephen M. Deusner wrote that the album "never really adds up to a particularly clear or bold statement," ultimately assigning it a score of 6.5 out of 10.

[12] In a more positive review for The Line of Best Fit, Erik Thompson gave Hard Love a 9 out of 10 and praised its optimistic tone.

"[16] To promote the release of Eraserland, Showalter (with Jason Isbell, Amanda Shires, My Morning Jacket members Bo Koster and Tom Blankenship, and Will Johnson) appeared on The Late Show with Stephen Colbert and performed "Ruby".