He is best known for his viral videos on YouTube, including his work under the moniker Postmodern Jukebox (PMJ) — an ever-evolving, revolving collective of performers playing popular music in period styles.

Bradlee grew up in the Pattenburg section of Union Township, Hunterdon County, New Jersey where he fell in love with jazz at the age of 12 after hearing George Gershwin's Rhapsody in Blue for the first time.

Bradlee became a successful performer in the New York jazz scene,[6] and served as music director for an interactive, off-Broadway theater experience called Sleep No More.

[7] In 2013, Bradlee began to work more seriously on forming Postmodern Jukebox, a rotating group of musicians producing covers of pop songs in alternate styles, including jazz, ragtime, and swing.

The group burst onto the public radar with their doo-wop cover of Miley Cyrus's "We Can't Stop", featuring Robyn Adele Anderson and guest artists, The Tee-Tones.

Postmodern Jukebox's October 2013 collaboration with Puddles Pity Party on a cover of Lorde's "Royals" generated particularly strong interest; as of June 2020, this video remained among the five most popular on Bradlee's YouTube channel with over 28.6 million hits.

In early February 2016, Bradlee and Postmodern Jukebox covered the late David Bowie’s classic song "Heroes" in honor of World Cancer Day – featuring vocals by Nicole Atkins.