In September of 1999, The Get Up Kids released Something To Write Home About. Their first for punk label Vagrant Records, the album marked a major step into bringing post-emo indie rock to the mainstream.

2001 saw the release of Eudora, a collection of covers and previously unreleased versions of songs.

May 2002 marked the release of the long-awaited third album, On A Wire, which alienated some older fans but attracted many newcomers to The Get Up Kids' music. The evolution of their music continued in March 2004 with the release of their fourth and final album, Guilt Show, produced by Ed Rose.

The Get Up Kids announced on Tuesday, March 8, 2005, via a heartfelt message on their website, that after ten years they were breaking up as a band. After announcing their breakup, The Get Up Kids went on a final fifteen stop tour, ending July 2, 2005 in their hometown, Kansas City, Missouri, at the Uptown Theatre.

After the break up, guitar player and vocalist Matthew Pryor dedicated himself to his side project The New Amsterdams.

A reunion show was officially announced on November 14th, 2008 along with the official confirmation of an album re-release and a 2009 national tour, including the 2009 Bamboozle and Groezrock festival.