Madeline began performing her songs in 2000 in Athens, GA, having grown up there. For a brief time in 2001, she fronted the locally popular dance-pop band Sugar Shakers with Tim Schreiber (now known as Timmy Tumble). She self-released her first album, "Kissing and Dancing," in 2002. It was later re-released by Plan-It-X Records. In 2006, she recorded “The Slow Bang” with Matthew Houck of Phosphorescent at his house in Athens for local label Orange Twin Records. On March 10, 2009, her third full-length album "White Flag" was released, having been recorded over a three-year period. Madeline described the recording of "White Flag" to Paste magazine as "totally different" compared to her previous albums:
For my past recordings, I usually sit down with a producer, and I play my song, and then the producer and I accompany them on various instruments. But this time, I recorded it mostly with a full band, so the recording process was completely different.
As of April 1, 2009, she handles the booking of her own shows and bartends on the side.
Madeline's writing has been described as "lyrics to be pored over," her voice as "haunting." Additionally, the weblog, "Moving Pictures and Random Noises," has described her compositional technique and style of folk singing as such:
Her music is brilliant, and it's not because she has complex arrangements or anything like that. It's brilliant because of its simplicity. She can fingerpick some notes and sing a song about grass and make it sound good. Her voice is just so pure. It's hard to place. It has a classic feel, like a singer off an old folk record. It's clear, light, soft, never intruding, just breezing through your ears. Her lyrics are also simple but honest. They're often cute and witty poetry, with a nice serious edge when she needs them to have one.