Both the album and their performance at that year's South by Southwest Music Conference were hailed by prominent artists and critics, including Rolling Stone's David Fricke and Steve Earle. Earle asked Marah to record for his label, E-Squared, and the results, Kids in Philly, was co-released by E-Squared and Artemis Records in 2000. Two years later, Marah released their third album, Float Away with the Friday Night Gods, which featured the Boss himself, Bruce Springsteen, on backing vocals on one track. By the time of 2004's 20,000 Streets Under the Sky, the group had moved to Yep Roc and picked up Superchunk's Jon Wurster on drums.

For the next album, the brothers Bielanko decided to record quickly and loosely, trying to capture the intensity and abandon of their live set. With the help of Kirk Henderson on bass and various keyboards, Mike Brenner on stringed instruments galore, and Wurster and Dave Peterson on drums, If You Didn't Laugh You'd Cry was a rambling, loose, and brilliant record that landed on many critics' best-of-the-year lists and won the group some big-name fans like writers Nick Hornby and Stephen King. The band also released a holiday record, A Christmas Kind of Town, at the same time. For the tour that followed the album's releases, the band solidified with Serge and David leading the way with support from Adam Garbinski on guitar, Peterson on drums, and Henderson on bass and keyboards.