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Leaving Through the Window is the second studio album and major label debut by American rock band Something Corporate. Following the success of the Drive Thru Records released Audioboxer (2001) EP, the band signed to their label distributor MCA Records in late 2001 after the EP caught their attention. The three month recording process for Leaving Through the Window took place in studios across California and Florida, with Jim Wirt acting as producer. A few songs from previous releases were re recorded for inclusion on the album; the material was anywhere from three months to three years old. A music video was made for "If You C Jordan" in early 2002; the group then embarked on a three month long US tour. After the tour, Leaving Through the Window was released jointly by Drive Thru and MCA Records on May 21. The band performed on the Warped Tour in 2002 and supported New Found Glory once on a European trek and again on a US tour through to the end of the year. A DVD single that featured music videos for "I Woke Up in a Car" and "If You C Jordan" was released during the US leg. 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". It was released as a UK single in early March and was promoted with a tour there; at the end of the month, "If You C Jordan" was released as a single. Leaving Through the Window sold 12,000 copies in its first week, charting at number 101 on the Billboard 200 chart in the process. It appeared on another Billboard chart, Heatseekers Albums, where it reached number one. "Punk Rock Princess" and "If You C Jordan" had some success: "If You C Jordan" charted at number 29 on Billboard Alternative Songs chart and number 68 in the UK; "Punk Rock Princess" charted only in the UK at number 33. As of mid 2005, the album's sales stood at 291,000 copies. The record received a mixed reception from critics, with negative comments on its length and frontman Andrew McMahon's vocals, and positive comments about his musicianship.

Something Corporate's debut album Ready Break was released through a local concert venue in November 2000. Before vocalist/pianist Andrew McMahon's final year of high school, guitarists Josh Partington and Reuben Hernandez left for college. Eventually, the two flew back to play gigs. Shortly afterwards, a number of record labels showed an interest in signing the group. Representatives from the label, The following month, the band signed to Drive Thru Records, leading to the release of Audioboxer in October. KROQ came across the EP and began playing the track "If You C Jordan" later that month. which had a distribution deal with Drive Thru that allowed MCA to upstream bands from them. In November and December, the group toured across the US with the likes of Reel Big Fish, Sugarcult and River City High.

Pre production began for Leaving Through the Window on Boxing Day 2001 and wrapped up in early January 2002. Main recording took place between January Three tracks—"Cavanaugh Park", "Straw Dog" and "Drunk Girl"—from Ready Break were also re recorded for the album. On two separate occasions, the piano was tracked in half time to give it a different sound. "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. 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." Discussing the album's title, McMahon said they wanted a name that was connected to some of the tracks, namely, to two lines in "I Want to Save You". He added that they lines "kind of reference the kind of getting in and out without being detected so that's how we came out with that". Musically, the album has been classified as alternative rock, It has been compared to works by bands like Jimmy Eat World, Cheap Trick, "I Want to Save You" is a character sketch of a girl who was mistreated by her partner. Discussing "Punk Rock Princess", McMahon said he was interested in a girl who liked punk rock music while he was in high school. The song served as a metaphor for what was a frequent discrepancy between the pair, which McMahon described: "She was cooler than I was and she liked punk and I was this, like, squirrely kid in, like, a piano band." The song had initially began as a ballad. They almost named it "I Woke Up in a Van", but felt that it did not fit as well as car did. The song references a show the band played in Poughkeepsie, New York at The Chance venue, It is about being bullied and using words to fight back. The track was not initially planned for release on the album and was meant to appear solely on the Audioboxer EP. "If You C Jordan" and "If I Were a Terrorist, I'd Bomb the Graduation" were written during the same period in 6/8 time. The band wanted both tracks to on the EP as an introduction to their music. However, "Terrorist" was left off the release because of the September 11 attacks; the group thought it would be in bad taste to use it. It lyrics reference space travel, which would continue to be an occasional theme in McMahon's songwriting. When Partington played the track for the band at practice, McMahon was enthusiastic about it. Sean Richardson of The Boston Phoenix said Partington's lyrical form was "more introspective and harder hitting than McMahon’s". it was named after a recreational area in Lake Forest, California. The park serves as a benchmark for incidents while growing up, like hanging out with friends and getting into trouble. The pop punk track "Fall" is followed by two indie pop songs, "Straw Dog" and "Good News"; the latter two, plus closer "Globes & Maps", showcased a sound that McMahon would later explore with his solo project Jack's Mannequin a few years later. In early February 2002, a music video was filmed for the track at El Segundo High School. It was directed by Richard Reines, who co founded Drive Thru Records and filmed over two 14 hour days. It opens with Chris Owen, who acts as Jordan the bully showing up to high school in a Porsche. The band takes musical equipment from the choir room and starts performing in the hallway. It concludes with them hanging out with Summer Altice. On February 25, the group performed the track on The Late Late Show with Craig Ferguson. On March 15, the album's title Leaving Through the Window was announced; later that day, the group worked on images for the album Following this, the group filmed a music video for "I Woke Up in a Car" in Toronto, Canada during an off day in between tours. Leaving Through the Window was released on May 21, 2002 as a joint release by Drive Thru and MCA Records. The UK edition, which was released on September 9,

Between late June and mid August, the group went on the Warped Tour (2002). 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. In October and November, the band toured across the US alongside New Found Glory, Finch and Further Seems Forever. A DVD single was released on November 5, featuring music videos for "I Woke Up in a Car" and "If You C Jordan". Following two European shows, the band went on a co headlining tour of the US with the Juliana Theory between January and March 2003, supported by Vendetta Red, Red West and Fiction Plane. On January 17, a music video was released for "Punk Rock Princess"; The latter track was initially planned for inclusion on the album, but was let off as the band thought it did not fit with album's flow. In March, the group went on a UK tour with Home Grown and Steel Train. On March 31, "If You C Jordan" was released as a single.