Most notably, Maxwell is the former lead singer of the swing revival band Squirrel Nut Zippers.

[2] During his time in What Peggy Wants, Maxwell befriended Metal Flake Mother drummer Jimbo Mathus.

In 1992, until Metal Flake Mother disbanded, Mathus became lead guitarist and Maxwell briefly joined as the band's drummer.

[3] In 1993, Mathus formed the neo-swing, pre-war jazz revival group Squirrel Nut Zippers with Katharine Whalen, Ken Mosher, Don Raleigh, and Chris Phillips, They played a couple of local shows and recorded a three-track EP on Merge Records.

In October 1995, the Sqirrel Nut Zippers went to New Orleans to record its Hot album at Kingsway Studios with producer Mike Napolitano.

In late December 2015, Maxwell published a piece on Medium explaining why he was not partiipating in the Squirrel Nut Zipper's 2016 tour.

[10] Maxwell was inducted into the North Carolina Music Hall of Fame in 2020 as a member of the Squirrel Nut Zippers.

In 2014, Maxwell and his family moved into Poplar Hill, a historic Greek Revival mansion in Hillsborough, North Carolina.

[12] They rented the former plantation home, which had once belonged to tobacco industrialist and white supremacist Julian Carr, but broke their lease due to what they reported were various hauntings.