Madilyn Bailey Bio
Madilyn Bailey Wold, professionally known as Madilyn Bailey, is an American singer, songwriter, musician, and YouTube personality from Boyceville, Wisconsin. Born on September 2, 1992, she first gained attention by posting cover songs on YouTube shortly before finishing high school, eventually building a subscriber base of about 9.54 million. She has released original EPs, a full-length cover album, and a catalog of singles promoted through live television appearances in both France and the United States.
Over the course of her career, Bailey has toured internationally, signed recording deals in France, and appeared on mainstream American television, including NBC’s Today and America’s Got Talent. She is known for blending pop vocals with acoustic instruments, drawing on influences such as Michelle Branch and Kina Grannis.
Early Life and Background
Madilyn Bailey Wold was born on September 2, 1992, in Boyceville, Wisconsin, to parents Greg Wold and Heidi Wold. Her father works for an advertising firm, and she grew up in a large household with five siblings. From an early age, music was a central part of her life, and she began to play music and write songs at the age of seven.
Bailey attended Boyceville High School, where she played in the school marching band and graduated in 2011. During her teenage years, she developed her vocal and instrumental skills, eventually learning to perform with vocals, guitar, ukulele, piano, keyboards, bass guitar, and drums. Before stepping into music full-time, she worked briefly as a certified nursing assistant, an experience that shaped her sense of discipline and stage presence.
Path to Music
Madilyn Bailey’s path to music began online. Shortly before graduating from high school, she started posting cover songs on YouTube, where her renditions of popular tracks quickly gathered more than 100 million views. The platform gave her a way to share her voice without industry gatekeepers, and her audience grew steadily as she refined her acoustic-pop style.
In 2012, Bailey joined the independent label Keep Your Soul Records to help produce and release her own material, and her debut original EP, Bad Habit, arrived that same year. A year later, in 2013, she made the move to Los Angeles to pursue music professionally. She soon joined Boyce Avenue on a tour of the United States and Canada, an experience she has described as her first taste of life on the road and an important step toward becoming a full-time touring artist.
Madilyn Bailey Career
Early Career (2008–2014)
Madilyn Bailey’s early career was built on YouTube, where she began uploading cover songs in 2008 while still a teenager. Her covers reached a wide audience, and the platform’s reach helped her connect with listeners well beyond Wisconsin. In 2012, she released her debut original EP, Bad Habit, marking her first official body of original work.
Her growing visibility led to a U.S. and Canada tour with Boyce Avenue in the second half of 2013, followed by her move to Los Angeles earlier that same year. These milestones established her as a working independent artist with an international online audience.
Breakthrough (2015–2019)
The year 2015 marked a major turning point for Madilyn Bailey when her cover of David Guetta and Sia’s “Titanium” received airplay on Virgin Radio in France. The song’s success led to a recording contract with PlayOn, a label under Warner Music Group, and it charted in both France and Belgium. A follow-up cover of Imagine Dragons’ “Radioactive” also charted, and in October 2015, she released the cover album Muse Box in France, supported by the single “Rude” featuring Flula. A fourth single, a cover of Cher’s “Believe”, arrived in early 2016.
Bailey continued to expand her catalog in 2016 with the release of her second original EP, Wiser, a five-track independent project. Her cover of “Titanium” was featured on the Australian television series Wanted that same year. In April 2018, she was selected as Elvis Duran’s Artist of the Month and appeared on NBC’s Today, hosted by Hoda Kotb and Kathie Lee Gifford, performing her original single “Tetris”. She also saw her song “Drunk on a Feeling” placed on the American action-drama series Station 19. In 2018, she held her first headlining show in Paris, and in 2019, she embarked on her first headlining full-band tour in China.
Notable Works and Milestones
Madilyn Bailey’s signature works include the original EP Bad Habit (2012), the cover album Muse Box (2015), the original EP Wiser (2016), and the single “Tetris” (2018). Her career-defining moments include signing with PlayOn in France, performing on NBC’s Today, and reaching millions of subscribers on YouTube, where she has become a defining voice in the online cover-song community.
Madilyn Bailey Personal Life
In 2014, Madilyn Bailey married James Benrud, and the couple has since built a life together in Los Angeles, California. In June 2023, she announced that the pair were expecting their first child, and on November 15, 2023, Bailey gave birth to a daughter.
Outside of music, Bailey has been open about her health, sharing in 2021 that she had been diagnosed with stage 4 endometriosis. She is also dyslexic, a condition she has discussed publicly. Despite these challenges, she has continued to release music, tour, and engage with her online audience.
Madilyn Bailey Family
Madilyn Bailey was raised in Boyceville, Wisconsin, by her parents Greg Wold and Heidi Wold, and she grew up alongside five siblings. Her father works in advertising, and music was a shared part of family life from an early age, with Bailey writing her first songs at seven years old. She later married James Benrud in 2014, and in November 2023, the couple welcomed a daughter, expanding her family further.