The three musicians came together to form the Lawrence Arms in 1999, taking their name from the apartment complex in which Kelly and McCaughan had lived before being evicted in the middle of the night.

Their most ambitious album to date, it demonstrated the band members' continued growth as musicians and songwriters and included extensive footnotes to the lyrics detailing their many references to history, literature, and pop culture.

Calcutta!, included a hidden track entitled "Warped Summer Extravaganza (Major Excellent)" referencing their attitude towards the tour.

[1] In December 2004 Kelly and Hennessy joined with fellow Chicago natives Dan Andriano of the Alkaline Trio (who had played with Kelly in Slapstick) and Todd Mohney, formerly of Rise Against, to form another band called the Falcon, and released an EP on Red Scare Industries.

The album was noted as faster and more energetic than the band's prior releases, with Kelly and McCaughan sharing lead vocals on every track.

[5] In March 2007, McCaughan released the debut album Four One Five Two from his acoustic side-project Sundowner, featuring two Lawrence Arms covers, one of which, "Boatless Booze Cruise" was originally sung by Kelly.

[6] The Lawrence Arms toured again in the fall of 2007, with their side projects the Falcon and Sundowner as openers along with the recently reunited American Steel.

[10] Titled Buttsweat and Tears, it was released on October 27 of that year through Fat Wreck Chords both as a 7-inch EP and as a digital download with an extra song.

[11][12] They then went on a tenth anniversary performance in October at the Metro Chicago, followed by a seven-date headlining tour of Arizona and California in November with Teenage Bottlerocket and Cobra Skulls as support.

[13][14] The band’s 10th-anniversary performance at The Metro in their hometown of Chicago was recorded and slated for a release on DVD by Crankstrap Productions.

However, complications that might have included logistics at Crankstrap, and/or might have included the band’s being audited by the IRS, meant that the DVD was consigned to purgatory until 2012, when Fat Wreck Chords announced that the video, titled An Evening of Extraordinary Circumstance, would finally be released on June 5[15] by them in collaboration with Crankstrap, a partnership previously announced in April 2011.

[16] The Lawrence Arms signed with Epitaph Records and released their sixth studio album, Metropole, on January 28, 2014, along with the News From Yalta 7-inch.