Born on Long Island, Bradlee relocated to New York City after studying jazz at the University of Hartford. While playing gigs at restaurants and nightclubs in New York City, Bradlee began experimenting with ragtime and jazz arrangements of pop tunes from the '80s, and he recorded several self-released digital albums of his offbeat versions of well-known melodies, as well as performances that interpolated seemingly dissimilar songs of different eras. Bradlee upped the ante on these experiments in 2012 with an album called A Motown Tribute to Nickelback, but as he began imagining a new platform for his experiments, he thought of YouTube, where he had been posting solo performance videos since 2009. In 2013, Bradlee began posting weekly videos in which he and a rotating cast of musicians and vocalists performed a new song each week, recorded live in a single take in Bradlee's living room. In September 2013, Bradlee posted his '50s-style reimagining of Cyrus' "We Can't Stop," and the clip soon went viral, racking up over four million views in less than two months and topping 14 million two years later.

Bradlee's Postmodern Jukebox channel was soon racking up Internet successes on a regular basis, and Bradlee continued to release both videos and albums based on his playful fun-house covers of popular songs. By 2015, Bradlee had made over 130 Postmodern Jukebox clips available online, and he and his crew were taking the show on the road, touring in North America, Europe, and the United Kingdom. Bradlee was quite prolific in 2016, with the release of several albums including PMJ and Chill and Swing the Vote! ~ Mark Deming