[2] Hogan was born in Atlanta, Georgia, the daughter of a Vietnam War Army veteran helicopter pilot who went on to become a policeman.

Because both her parents worked, Hogan and her siblings spent most of their time with her grandmother in her apartment in midtown/downtown Atlanta growing up, where they listened to country music station WPLO.

[16] Her debut solo record, The Whistle Only Dogs Can Hear, was released in 1996, and contained covers of songs by Will Oldham and Vic Chesnutt.

The album is a collection of songs either written for her or chosen for her by songwriter friends Andrew Bird, Vic Chesnutt, Jon Langford, Stephin Merritt, M. Ward, and others.

[19] As of 2021, Hogan continues to occasionally perform as singer/bandleader, especially in Chicago, often with accompanying musicians such as Nora O'Connor and Andy Hopkins,[24] and with the Flat Five.

[29] Hogan appears on records by Mavis Staples, The Mekons, Will Oldham, Matt Pond PA,[30] Amy Ray, Giant Sand, Archer Prewitt, Alejandro Escovedo, Drive-By Truckers, Jakob Dylan,[31] and Tortoise, among others.

[22] These recordings include: A select discography:[44] From 1998 to 2008 Hogan worked as a bartender at The Hideout, a music venue in Chicago known for putting on an annual block party in September.

[54] As of 2013, Hogan once again was working as an assistant for her friend, American cartoonist and author, Lynda Barry,[55] helping her arrange her teaching schedule.

[5][56] In one episode of Barry's Ernie Pook's Comeek, children are peering in a window of the Hideout nightclub in Chicago, listening to Hogan's band The Wooden Leg.