Following the release of Living Well Is the Best Revenge (2002), MCA was merged into Geffen Records, and the band was not picked up by the latter label.

The group spent time writing on their next album and following a meeting with Butch Walker, moved to Atlanta, Georgia, to start recording the new material.

The album is classified as an emo and pop punk release; its songs were compared with those of Division of Laura Lee, Recover and Jimmy Eat World.

Music critics gave the album a mixed reception with some complimenting its energy and sound, and others finding it average.

In 1999, Midtown signed to the independent label Drive-Thru Records and released their debut album Save the World, Lose the Girl (2000) through it.

[4] According to drummer Rob Hitt, MCA had a few groups that performed well commercially and Drive-Thru "wanted to put every other band into that same cookie-cutter mold.

[5] They wanted a rawer sound compared to the polished direction of the last two albums, both of which were produced by Mark Trombino.

[11] All the recordings, but "Give it Up", were mixed by Walker and Russ T, and mastered by George Marino at Sterling Sound in New York City.

"Give It Up" was mixed by Jay Baumgardner and mastered by Vlado Meller at Sony Music Studios, also in New York City.

[14] While writing the album, Saporta was "going through a tough time, where everything that I thought I knew was proven to be false and the world just started redefining itself".

acts as an introduction and has gang vocals shouting the phrase "So hard to believe you what you're looking for"[14] before segueing into the post-punk track "To Our Savior", which is similar to the output of the Swedish band Division of Laura Lee.

features a toy piano and is followed by an instrumental interlude titled, "God Is Dead," which is an extrapolation of the vocal melody on the following track, "Whole New World.

[20][16] Between late April and early June 2004, Midtown went on a co-headlining US tour with Armor for Sleep and Your Enemies Friends; they were supported on select dates by Time and Distance, the Working Title, Stars Hide Fire, Vise Versa, Emanuel and Lance's Hero.

[31] The group was initially scheduled to appear on the Warped Tour between mid-June and mid-August[32] but pulled out of all of the shows except the last five.

[35] "Sister Golden Hair", a cover of the America song recorded during the album's sessions, was released in November 2006.

[12] In a review for Blender, journalist Maura Johnston said the album only missteps when the tempo "slows down and [Midtown's] peppy embrace of nihilism and nothingness stops pogoing".

[37] Ox-Fanzine's Kid Dynamite viewed it as "unfortunately only mediocre", noting the "catchy melodies, polyphonic vocals, variety … the whole thing never seems too pop".

"[14] He regarded it as "more fluid and energized" than the group's preceding album but said it is "hardly as bold or invigorating" as their debut release.

[14] AllMusic reviewer Johnny Loftus complimented the group's "leaner, more moody sound" despite them abandoning "sugar-high" hooks for "less direct yet still succinct songcraft".

[13] Loftus said the release is not "a sun-and-sand summertime record" but it set the stage for "kids making the transition from goofy preteen pop-punk to bands like the Alkaline Trio".