[4][a] Following Sample's death, Arie put work on Christmas with Friends on hold for a year,[4][8] after which she decided to contact multiple singers to complete the project.

[6][9] The artists who appear on the album are Kem, Brandy, Michael McDonald, Dave Koz, Tori Kelly, and Trombone Shorty.

[3] Arie said that Sample's chord voicings had a deep impact on her approach for her vocals; she explained: "His piano playing was so nuanced and delicate, it made me want to sing in a way that would complement his aesthetic.

"[11] Charles wrote that "Let It Snow" features "Sample's glib piano work and her feathery croon" and "The Christmas Song" as a "smoke-infused ditty".

[7][10] Her versions of "Let It Snow" and "God Rest You Merry, Gentlemen" incorporate a jazz sound,[12][13] while her take on "Auld Lang Syne" includes an instrumental from American saxophonist Kirk Whalum.

[2] Christmas with Friends was Sample's final album before his death; when talking about her part in his career, Arie said: "It's an honor to be the gatekeeper to what we believe is his last recorded work.

The seven-city production started in Boston on December 13, 2015, with American musician Jonathan McReynolds serving as the opening act for five of its dates.

Praising Arie's performance as "show[ing] a smooth maturity", The Southern Illinoisan's Pablo Gorondi wrote that Sample lent the album a "jazz expertise".

[10] Sean L. Maloney of the Nashville Scene summed up the record as "a great big bundle of warm-and-fuzzies, a cozy cuddle by the fireplace on a cold night, and a holiday tradition in the makin".

[3] While she believed that the album needed more uptempo tracks, Melody Charles responded positively to Arie's vocals and her collaborations with the other artists.

She wrote that the album "gift[ed] music lovers with a treat to the ears, and heart, long before that celebrated day arrives".

[7] Joe Szczechowski of Digital First Media praised Arie's approach to the album's various genres, but he criticized her tendency to rely on "runs and other vocal gymnastics when the song would be best served by simply carrying the tune".

[23] Along with the album, Arie's cover of "Merry Christmas Baby" peaked at number 28 on the Billboard Hot 100 on January 9, 2016, and remained on the chart for one week.