Frank Sinatra, the iconic “Chairman of the Board,” left behind a rich legacy of music, including a notable collection of Christmas albums. However, for fans seeking to collect his holiday tunes, the sheer volume of reissues and compilations can be overwhelming. This guide aims to demystify Frank Sinatra’s Christmas releases, helping enthusiasts acquire his festive music efficiently and avoid unnecessary purchases of repackaged content.
Understanding Sinatra’s Official Christmas Albums
Frank Sinatra released four primary albums dedicated to Christmas music across different record labels:
Christmas Songs by Sinatra (Columbia, 1948)
This foundational album originally featured eight songs. Over the years, Columbia has reissued this work multiple times, often adding previously unreleased tracks recorded for troops during World War II (V-Discs). While numerous “versions” exist, a CD reissue that includes these bonus tracks is a comprehensive choice for collectors. Budget releases also emerged to compete with Sinatra’s later Capitol recordings.

A Jolly Christmas from Frank Sinatra (Capitol, 1957)
Considered by many to be a classic, this album comprises most of Sinatra’s Capitol Christmas recordings. It originally contained twelve songs. While many versions are available, some feature updated cover art that might appear less “old-fashioned” but does not alter the core musical content. Owning any version of this album provides a solid foundation for a Sinatra Christmas collection.

12 Songs of Christmas (Reprise, 1964)
Recorded with Bing Crosby and Fred Waring and the Pennsylvanians, this Reprise release is often overlooked. It features five songs with Sinatra’s prominent involvement. Notably, this album has primarily been available on vinyl and has not seen a CD release. However, the Sinatra tracks from this collection have been included in various later compilations.

The Sinatra Family Wish You a Merry Christmas (Reprise, 1969)
This album is a heartwarming collection, featuring a particularly poignant song by Nancy Sinatra. While it was released on CD in 1999, copies can be rare and expensive. Fortunately, the songs featuring Frank Sinatra from this album are also available on compilation albums, and the album itself can be found on digital platforms like iTunes.
Cover of "The Sinatra Family Wish You a Merry Christmas"
Navigating Compilations and Reissues
The record industry’s practice of re-releasing and repackaging music can lead to confusion. Record companies frequently mine existing recordings, altering artwork and tracklists to create the illusion of new material. When considering compilations, it’s essential to understand what content they offer and compare it to the original albums.
Key Sinatra Christmas Compilations:
The Sinatra Christmas Album (2003): This CD effectively gathers all of Sinatra’s Reprise-era Christmas music, including tracks from 12 Songs of Christmas and The Sinatra Family Wish You a Merry Christmas, along with a 1975 single.
Cover of "The Sinatra Christmas Album" (2003)Frank Sinatra Christmas Collection (2004): This compilation features songs from 12 Songs of Christmas and Sinatra Family, alongside “I’ve Got My Love to Keep Me Warm” from Ring-a-Ding-Ding! and other recordings, including a rare “Silent Night.”
Ultimate Christmas (2017): A more extensive compilation, it includes Capitol single versions, several tracks from A Jolly Christmas, all of Sinatra’s songs from 12 Songs of Christmas and Sinatra Family, the 1975 single, and “Silent Night.”
Cover of "Ultimate Christmas" (2017)
Compilations to Approach with Caution:
Christmas: This compilation, often noted for its confusing mix of Capitol-era recordings and gospel songs with the Charioteers, is generally considered redundant and unnecessary for serious collectors.
The Classic Christmas Album: The title is a misnomer, as this collection primarily consists of Columbia Christmas recordings mixed with earlier gospel tracks, offering little unique value for Sinatra’s Christmas music.
Covers of potentially redundant compilations
Conclusion: Play Ball Wisely
For dedicated fans, the allure of a new compilation, even with just a few unreleased tracks, can be strong. However, record companies profit from this desire by continually repackaging Sinatra’s Christmas music. By understanding the original albums and the content of various compilations, collectors can make informed decisions. Owning the four core albums provides the essential foundation, and careful selection of compilations can fill any remaining gaps without unnecessary duplication.
Embark on your journey to collect Frank Sinatra’s festive music with clarity and discernment. Happy hunting!
Share this:
- Share on X (Opens in new window) X
- Share on Facebook (Opens in new window) Facebook
Like Loading…

Cover of "The Sinatra Christmas Album" (2003)
Cover of "Ultimate Christmas" (2017)
Covers of potentially redundant compilations