The Upsides is a part of a trilogy (along with Suburbia I've Given You All and Now I'm Nothing [2011] and The Greatest Generation [2013]) that dealt with vocalist Dan Campbell's struggles of being scared, loneliness and feeling lost.

[2] As vocalist and lyricist Dan "Soupy" Campbell explained on the album's vinyl release, The Upsides is about fighting back.

Although it seemed the members of the band had been beaten into misery in their early 20s, Campbell, after riding past a fountain at "Logan Circle" and seeing it had been switched on, realized it wasn't right for him to feel defeated at 23.

The lyrics also venture into different themes in each song, from the loneliness of tour life ("Everything I Own Fits in this Backpack"), to social awkwardness ("This Party Sucks") and persevering through bad times ("Washington Square Park").

[4] Allmusic's review said The Upsides has a concept album-like feel and is filled with "post-college angst, busted hearts, big questions, hope, anger, humor, and life", adding that the songs fit together like an intricate puzzle, flowing like it was an entire diary's worth of observations, feelings and events.

[6] On November 11, 2009, The Upsides was announced for release in two months' time; alongside this, the track listing was posted online.

The first of the reworked songs was a take on "Dynamite Shovel"; "Recorded live in one room with a bunch of mics everywhere, this finds us stomping and clapping and yelling and laughing".

This time it features new artwork and all the bonus tracks made available with the previous deluxe edition of the album, in addition to "Leavenhouse.

Reviewer Tim Sendra complimented the dueling riffs of guitarists Matt Brasch and Casey Cavaliere, Mike Kennedy's drum work and how Nick Steinborn adds the occasional unobtrusive keyboard part: "They simply take the best of each element of their conglomerated sound (the hookiness of pop, the heart-spilling fever of emo, the rambling energy of punk) and let it rip.