While vocalist India.Arie and keyboardist Joe Sample worked on new songs that, in Arie's words, "weren't coming together as quickly as I wanted," Arie had the idea to shift direction and record a Christmas album — something her mother had been wanting her to do. Sample's own family members had been asking the same from him, so he was happy to go along. In September 2014, while Christmas with Friends was being completed, Sample — whose importance to jazz and R&B is difficult to overstate — died of mesothelioma. He plays piano on four of the ten songs: the opening "Let It Snow," "Silent Night" (featuring Brandy), "Have Yourself a Merry Little Christmas" (featuring Kem), and "The Christmas Song." It's unfortunate that Sample isn't heard more frequently, but the whole album is loose and lively, supported by drop-ins from contemporary gospel, jazz, pop, R&B, and rock artists, including Michael McDonald and Trombone Shorty. The backing musicians, such producer Aaron Lindsey, Jeff "Tain" Watts, and Nathan East, are top-notch as well, and Arie ties it all together, switching between the spiritual and playful material with natural ease.