My Teenage Stride started in 2003 as "the bedroom/hallway/basement recording project of Jedediah Smith," providing a band identity for Smith's multi-instrumental solo recordings. Over the years, the group has consisted of Jedediah Smith and a shifting cast of band members. Smith grew up in the rural Western Massachusetts town of Colrain, learning piano, guitar, bass and drums as a teenager. As Smith described it, "My grandmother was a stride piano player, Jelly Roll Morton-style... She almost went professional, but because she was a woman in the '20s I don't think she felt she'd be able to go all the way with it. My mom started singing jazz after she turned 40, and my dad had an incredible record collection." The first My Teenage Stride album, A Sad Cloud, was released on the Banazan label in 2004, followed the following year by Major Major on Becalmed Records. Smith recruited Michael Hollitscher on bass, Brett Whitmoyer on drums, Tris McCall on synthesizer, and Dakkan Abbe on guitar; this line-up recorded part of the third album, 2007's Ears Like Golden Bats, though much of the album consisted of Smith still playing every instrument. Ears Like Golden Bats was described by eMusic.com as "one of the year's most thrilling surprises, an album that wraps wry gallows humor in glistening guitars and whistling synths." The review continued:
Lyrically, Smith is a gleeful malcontent. The first words on the record are "God bless the criminal," and its remainder is filled with tales of sad sacks and pessimists who never built a bridge they wouldn't burn. "Reversal," a canny re-write of the Chills '"Pink Frost," is one long festival of denial, Smith grimly intoning: "When you feel alright/ reversal!/ when you sail alright/ reversal!"
In 2008, the group self-released an EP called Lesser Demons, and in December 2008, recorded a festive tune for the Christmas compilation 'An Indiecater Christmas' released by Indiecater Records. My Teenage Stride undertook to release a single each month in 2009, with releases on eMusic.com that included some b-sides and two EPs. As of 2010, My Teenage Stride was a trio with Smith, Edd Chitenden, and John Grewell. They released a set of five songs, recorded earlier in 2010 by Smith alone, on WFMU's Free Music Archive. In early 2010, the group solicited funding on Kickstarter for a new album, citing a plan to work with producer/musician Marc Kramer.
