According to jazz musician Greg Gordon Smith, the album came into being after he first heard Guarini singing in a club. Impressed by Guarini's vocal skills, he approached Guarini to collaborate on music, eventually becoming the arranger/pianist on the album. Smith also wrote the album's title track. In an interview for the blog site Essential Justin Smith made this comment about Guarini, "What we're all really hoping for as artists is to know that someone heard us and really felt something. Justin had that effect on me when I first heard him sing. "Stranger Things" was my attempt to put that phenomenon into music and relate it to his experiences lyrically". He also said of Guarini, "Anyone else as gifted as Justin would be arrogant, especially in this business. He is never anything but a pleasure to work with and be around".
Other talented jazz musicians became involved, resulting in a quartet made up of a pianist (Smith), drummer (Jamey Tate), bassist (Ian Martin), and saxophonist/flutist (Katisse Buckingham). Eventually the quartet recorded tracks with Guarini at Firehouse Studio, a recording studio in Los Angeles, California. In an informal conversation, the album's drummer described Guarini as "nails in the studio" and someone who "sings from the heart". Flutist Buckingham told his story of initially being reluctant when first approached because of the American Idol connection (although he admittedly had never watched the show and was unfamiliar with Guarini), but quickly changed his mind after hearing Guarini sing a portion of "My Funny Valentine" in 5/4 time.
The album of reinvented jazz classics was described by AllMusic as "a successful reinvention... where his natural skills shine", and that Guarini's "charisma when contrasted with his band's jazz chops has a nice, relaxed appeal".The Philadelphia Inquirer likened Guarini to "an earthier Al Jarreau" saying of the album, "Guarini displays an agile, attractive voice with good phrasing, supported by a sophisticated and funky backing ensemble".