Christmas with Sinatra and Friends works because Sinatra sounds his best when he's around other people.
It seems odd in 2009, more than ten years after Frank Sinatra's death, to be finding new Christmas compilations featuring old recordings, somehow rearranged to represent a take on a Sinatra Christmas different than the ones that have come before it. Stranger still is that the recordings from the "friends" who appear on the album don't have any obvious connection to Sinatra other than that they are of Christmas songs in a similar style to the ones Sinatra himself recorded. And yet Christmas with Sinatra and Friends works for many of the same reasons that the previously released Christmas with the Rat Pack works. Most importantly, Sinatra sounds his best when he's around other people.
Sinatra's immediately identifiable baritone, for all of its signature character and charm, is not what one would call a versatile instrument -- at least, not in this context. His songs are sung with a sort of reverential majesty, a technique that works brilliantly on something like "The Little Drummer Boy", but less so with the context of frivolity, as on "Santa Claus is Coming to Town". Having other artists show up every two or three tracks breaks up what could turn to monotony, and despite the incongruity of some of the guest recordings being from the '90s while Sinatra's are largely from the '50s and '60s, hearing Mel Tormé sing his own "The Christmas Song" and Rosemary Clooney on "White Christmas" breaks up the proceedings nicely. It's not by any means a defining collection of works, but as a simple collection of songs for Christmas, one could certainly find worse than Christmas with Sinatra and Friends.