Historical Misappropriation (Album) — Scott Bradlee & Postmodern Jukebox, 2014

Here’s an album that will definitely help you bridge the musical generation gap. Not just another cover album, it’s an amazing collection of current pop, hip-hop and rock hits completely reimagined. These arrangements — which could be mistaken for jazz and swing gems from decades ago for those unfamiliar with them — are the brainchildren of 33-year-old Scott Bradlee and his Postmodern Jukebox (a band of rotating singers and jazz musicians). The first track, “Rude,” transforms a reggae rock hit by Magic into a doo-wop tune with the heartthrob crooning of Von Smith and backup vocals reminiscent of the Shangri-las. Then there is the reimagined Britney Spear’s tune “Womanizer” that transports you to a smoky speakeasy where a singer in the vein of Shirley Bassey serenades your ears. Perhaps the best reimagining on this album was of this summer’s biggest hit from pop sensation Meghan Trainor, “All About That Bass,” now slowed to a sultry tempo with the buttery-toned jazz singer Kate Davis providing lead vocals and playing standup bass. Gorgeous stuff.

Pure Imagination (Single) — Fiona Apple, 2013

Chipotle (yes, the restaurant chain) has been working with musicians to create compelling reimagined songs for its brand awareness campaign, hoping to provide a stark comparison between them and other fast food restaurants. Many of these videos have gone viral and become musical hits of their own. Fiona Apple was one of those artists who lent her talents to Chipotle’s cause and performs a dark rendition of “Pure Imagination” from the 1971 classic film Willy Wonka and the Chocolate Factory. Unlike the original film score’s happier tone, Fiona’s version has a brooding and dystopian soul to it, albeit with a message of hope and change in the lyrics. Without imagination, no new ideas or changes would ever be free to see the light of day, and this song exhorts us to use our imagination more and often. To experience the full impact, watch the video on YouTube.

With Imagination (I’ll Get There) (Single) — Harry Connick Jr., Blue Light, Red Light, 1991

This Dixieland jazz/gospel-inspired track treats your ears to the New Orleans jazz style that Harry Connick Jr. helped revive in the early 1990s