Midtown released their debut album Save the World, Lose the Girl through independent label Drive-Thru Records on February 15, 2000.

[1] Initial promotion consisted of supporting slots for New Found Glory, All and Reel Big Fish, and an appearance on that year's Warped Tour.

[4] After the conclusion of this trek, the band traveled to California,[5] where they spent three weeks in pre-production working on 20 songs, which had been whittled down from 30.

[10] Living Well Is the Best Revenge continued the pop punk sound of their debut,[14] earning comparisons to Good Charlotte and Fenix TX.

[17] Leading up to New Years Day 2002, the band embarked on a brief east coast tour, in addition to playing some shows with Good Charlotte and Mest.

[27] Rann mentioned that the sole tie that they had with Drive-Thru at this point was the label being contractually obliged to have their logo on the back cover of the album, and he had not "spoken to any of the people there in over a year".

[29] The following day, the band held an interview with AbsolutePunk where they discussed their disintegrating relationship with Drive-Thru and their appraisal of MCA.

[31] When Punknews.org reported on the interview, a firm on behalf of Drive-Thru threatened to sue some of their users for libel if they did not remove specific comments.

Modern Fix called it "too poppy", before clarifying that they've "listened to this album way too many times to justify that as a negative comment.

"[48] Margie Libling of Ink 19 wrote that it was a "perfect blend of melodic yet driven tracks" signalling itself out as "an original and distinct album.

[21] Punknews.org staff member Scott Heisel complimented Trombino's "crystal clear" production, enabling the group to come across "as loud as possible" while still leaving "space for [them] to grow".

[17] Melodic's Johan Wippsson viewed the band as more enjoyable to listen to than their peers, finding the tracks were "on a good level all through[out]".

[46] The "saccharine melodies and vocal harmonies" could make the listener "quite ill," if they were not "accompanied by rarely less than buzzing energy levels and some seriously addictive hooks.

"[46] AllMusic reviewer Heather Phares said it "picks up more or less" where their debut album "left off, delivering plenty of revved-up, melodic punk-pop.

[18] Slant Magazine's Aaron Scott said the despite Saporta's voice having "previously combined snottiness with catchiness", the record displayed "melodies lacking both attitude and pop hooks.

All lyrics written by Gabe Saporta, except "Perfect" and "Find Comfort in Yourself" by Hearth Saraceno, and "One Last Time" by Tyler Rann.