[6] Madilyn Bailey began her career shortly before graduating from high school[8] by covering popular songs and posting them on YouTube, gathering over 100 million views.

[3] In 2012, Bailey joined Keep Your Soul Records to assist with the production of her material and moved to Los Angeles in 2013.

[3] In 2015, her rendition of the song "Titanium", originally by David Guetta and Sia, gained airplay on Virgin Radio in France.

In October 2015, Bailey released an album of covers in France, entitled Muse Box, supported by the single "Rude" feat.

She was featured on NBC's Today show hosted by Hoda Kotb and Kathie Lee Gifford, broadcast nationally in the United States on April 20, 2018, where Bailey performed a live version of her single "Tetris".

In 2018, her original song "Drunk on a Feeling" was featured on the American action-drama TV series Station 19.

In 2021, Madilyn appeared on the 16th season of America's Got Talent, performing an original song made out of hate comments, which had gained over 20 million views on YouTube.