The three-month recording process for Leaving Through the Window took place in studios across California and Florida, with Jim Wirt acting as producer.
They co-headlined a three-month US tour with the Juliana Theory, which coincided with the release of a music video for "Punk Rock Princess".
[2] Before vocalist/pianist Andrew McMahon's final year of high school,[3] guitarists Josh Partington and Reuben Hernandez left for college.
[4] After finalizing their line-up, the group began performing at local venues, eventually gaining support slots for bands like Better Than Ezra and Sugar Ray.
[14] In November and December, the group toured across the US with the likes of Reel Big Fish, Sugarcult and River City High.
Smith provided background vocals on "Punk Rock Princess", "I Woke Up in a Car", "The Astronaut", "Hurricane", "Straw Dog", "Drunk Girl" and "Not What It Seems".
[20] "Punk Rock Princess" and "Hurricane", both of which featured on the Audioboxer EP, were re-recorded for the album as the group wanted to be "happier with their execution", according to McMahon.
[20] McMahon found it easier coming up with arrangements on the piano, rather than a guitar, as it seemed a better instrument to expand song structures.
"[21] "Punk Rock Princess", "Cavanaugh Park", "Straw Dog" and "Globes & Maps" feature string arrangements written by Paul Buckmaster who conducted the 26-piece orchestra that performed them.
[22][23] Partington described the album as a "conglomeration of songs that were anywhere from three months to three years old ... like a greatest hits of our early stuff.
[28][29] It has been compared to works by bands like Jimmy Eat World, Cheap Trick,[26] Lit,[28] and New Found Glory.
[30][31] Austin Saalman of Under the Radar wrote that the album was a "a warm concoction of guitar-heavy pop-punk and emotive piano rock, charmingly complemented by [...] McMahon’s naive boy-next-door lyrical sensitivity".
A day or two after it ended, McMahon sat in his parents' garage, where his piano was situated and wrote the song around his memories of the tour.
The song references a show the band played in Poughkeepsie, New York at The Chance venue,[25] as well as to Rockford, Illinois.
[53] Following this, the group toured across Europe supporting New Found Glory in August and September, before headlining two shows in the UK and four in Japan.
[60] On January 17, a music video was released for "Punk Rock Princess";[57] it was filmed the previous December in Toronto, Canada.
AllMusic reviewer Alex Henderson wrote the group's style was "punky yet vulnerable and introspective", with McMahon "anchoring" many of the songs around his piano.
"[26] CMJ Music Monthly writer Michelle Kleinsak said McMahon's musicianship on the piano disconnects the group from their emo/punk peers, and helps make their album "such an elegant and confident debut.
"[68] Melodic reviewer Kaj Roth wrote that the "real nice" record was filled with "loads of catchy tunes" that are "perfect for the radio this hot summer.
"[28] Richard Abowitz of Rolling Stone noted the band crafted "suburban ennui and high school angst into slick, hummable punk.
"[67] Sputnikmusic emeritus Andrew H. viewed the album as "pretty average", though he found the lyrics/vocals "really personal", adding that some listeners would dislike McMahon's voice.
[22] The staff at Modern Fix noted that the keyboard would struggle to compete with the loudness of the guitars and McMahon's vocals, while praising their "excellent grasp on constructing songs that have defined parts and movements, flows and sways".
[31] In spite of this, he said the group seemed "pretty proficient at writing a good pop song" and praised McMahon's vocals.
He criticized the album's length, wishing the band had left "at least a minute from each song on the studio’s floor, where they belong.
"[71] Drowned in Sound's Peter White dismissed the album as an "XFM playlist without the edge" that "makes a mockery of all things beautiful about the joy of discovery and the fun of breathing.
[83] In his retrospective piece, Saalman wrote that the album, "remains a significant act within its genre’s canon, its songs forming a collective portrait of late-’90s and early-’00s American youth culture".