The band was formed by guitarist John Nolan and bassist Shaun Cooper, after both of them left Taking Back Sunday in early 2003.

Straylight Run tracked it at Apple Head Studios in Woodstock, New York, between March and June 2004, with producers Michael Birnbaum and Chris Bittner.

The band embarked on several accompanying tours across the United States with the likes of Hot Rod Circuit, Something Corporate, and Firescape, as well as delivering performances for The Bamboozle festival and on Last Call with Carson Daly.

The music on Straylight Run moved away from the emo sound of Taking Back Sunday, transitioning into piano-centred indie rock material, drawing comparisons to the Anniversary and Bright Eyes.

Taking Back Sunday released their debut studio album Tell All Your Friends in 2002; the band found themselves at the forefront of the emo music scene.

[2][3] In May 2003, John Nolan and Cooper formed a new band; the pair tracked demos with the aid of Taking Back Sunday drummer Mark O'Connell.

When they felt ready to debut the band to the wider public, they settled on the name Straylight Run, after a large amount of discussion and debating.

[4] In August 2003, Nolan and Cooper featured on a radio showcase, where they promoted the band; shortly after the appearance, fan-recorded versions of the songs were posted on the internet.

[9] Around this time, Straylight Run were attracting offers from major labels as well as interest from music producers and managers who wished to work with them.

[4][10][11][12] Straylight Run spent most of December 2003 working on new material and making plans to record their debut studio album, before supporting Brand New on their tour of the United Kingdom in January 2004.

[14] In March 2004, the band travelled to Woodstock, New York, to record the album at Apple Head Studios, away from John Nolan and Cooper's hometown of Amityville on Long Island.

[23][24] Straylight Run's opening track, "The Perfect Ending", contains only John Nolan's vocals over pianos, alongside accompanying bells by Noon.

"[27] "Tool Sheds and Hot Tubs" features up-tempo electronic instrumentation, which includes synths, earning it a comparison to work of I Am the World Trade Center.

[34] On January 7, 2005, Straylight Run won a fan-voted contest on Launch.com, which earned them the spot to deliver a live-in-the-studio performance of "Existentialism on Prom Night".

[39][40] AllMusic reviewer Johnny Loftus said that the while Straylight Run includes some elements of emo, the "songwriting is more varied than many in that genre offer in the mid-2000s."

"[21] In a brief review, the staff of Spin compared Nolan leaving Taking Back Sunday to form Straylight Run with "trading the football team for the choral society.

"[42] Sputnikmusic's Adam Downer found the album to be "an amazing, beautiful piece of work" with "some truly sensational anthem-ballads" and "solid tracks in the middle."

Music reviewer Rob O'Connor noted that the "emphasis here is more on texture than catharsis," save for the "epic sense of drama of an '80s power ballad" in two of the tracks.

He said that Michelle Nolan's vocal appearance serves as "an extra change-up," with the rest of the band "turn[ing] 'twee' for a moment of heavenly shuffle" on "Tool Sheds and Hot Tubs".

[25] Kaj Roth of Melodic wrote that Straylight Run "takes you on a trip over the clouds in the atmosphere" with the "dreamlike and emotional vocals perfectly packaged.

"[43] LAS Magazine's Natalie B. David considered the tracks with Nolan on lead vocals to be the weakest on the album, while also saying that a number of the songs "would be severely lacking without her.