The Essential Frank Sinatra Christmas LP Guide: A Festive Deep Dive

Frank Sinatra, the undisputed Chairman of the Board, conjures images of swinging rhythms and ring-a-ding-ding energy. So, when the holiday season rolls around, many naturally anticipate a similarly high-octane festive soundtrack from Ol’ Blue Eyes. However, diving into the Frank Sinatra Christmas Lp collection reveals a different, often more nuanced, side of the legendary vocalist’s holiday spirit. While moments of jauntiness exist, Sinatra’s primary Christmas output leans towards reverence, nostalgia, and warmth, offering a sophisticated alternative to purely upbeat seasonal fare.

Sinatra recorded Christmas music across his three major label affiliations: Columbia, Capitol, and Reprise. His journey into holiday recordings began relatively early in his career.

Early Christmas Cheer: Columbia Records Era

Sinatra’s first foray into Christmas music dates back to November 14, 1944, with his recording of “White Christmas” during his time at Columbia Records. This track, recorded during only his sixth session for the label, marked the beginning of a series of Christmas singles released over the subsequent years. Eventually, Columbia gathered these festive offerings into his first dedicated holiday album.

Album cover for 'Christmas Songs by Sinatra' (1948 Columbia Records release), an early Frank Sinatra Christmas LP.

Christmas Songs by Sinatra (1948)

Released initially as a set of 78 RPM records and later as a 10″ LP, Christmas Songs by Sinatra was only his third album release. By this time, Bing Crosby had already established the tradition of popular artists releasing Christmas records, with his own Merry Christmas LP becoming a perennial bestseller. Sinatra and Columbia followed suit with this eight-track collection. It features a mix of contemporary holiday songs and traditional carols. Notably, Sinatra tackles “Jingle Bells” and “Santa Claus is Comin’ to Town.” While performed with Sinatra’s characteristic vocal charm, these versions possess a certain formality compared to Crosby’s contemporary, high-energy recordings of the same songs with the Andrews Sisters, which brimmed with infectious swing.

A 1994 CD reissue expanded the collection, adding tracks like “Christmas Dreaming (a Little Early This Year)” and “Let It Snow! Let It Snow! Let It Snow!” recorded around the same period. Curiously, this reissue presented alternate takes for five of the original eight tracks instead of the master versions. Bonus content included rehearsal excerpts and V Disc recordings made for troops overseas during WWII, featuring carols and a pleasant “Winter Wonderland,” alongside more solemn renditions like “The Lord’s Prayer” and “Ave Maria.” Acquiring Christmas Songs by Sinatra is essential for a complete overview of his holiday work, offering a pleasant, if not groundbreaking, listen from his early career. Potential buyers should be aware that these Columbia-era tracks have appeared on numerous compilations with varying artwork over the years.

The Capitol Years: A Sumptuous, Solemn Holiday

Sinatra’s move to Capitol Records marked a creative peak, yielding iconic concept albums. His primary Christmas statement from this era reflects a more mature, orchestral approach.

Album cover for 'A Jolly Christmas from Frank Sinatra' (1957 Capitol Records), a key Frank Sinatra Christmas LP featuring arrangements by Gordon Jenkins.

A Jolly Christmas from Frank Sinatra (1957)

This Frank Sinatra Christmas Lp, arranged and conducted by the masterful Gordon Jenkins, is a lush, sophisticated recording. Jenkins, known for his sweeping string arrangements capable of conveying both soaring joy and profound melancholy, provides a backdrop far removed from the brassy swing of Nelson Riddle or the bold orchestrations of Billy May, collaborators Sinatra worked with on other seminal Capitol albums. The partnership with Jenkins signals that this album, despite its title, prioritizes warmth and reverence over high-energy revelry.

Alternate artwork associated with Frank Sinatra's Christmas music from the Capitol era, featuring a portrait of Sinatra.

The album opens with a delightful mid-tempo version of “Jingle Bells,” featuring Jenkins’ choir adding playful vocal flourishes. Following this, the first side focuses on popular contemporary Christmas songs. Among these are “Mistletoe and Holly,” a charming tune co-written by Sinatra himself, and “The Christmas Waltz.” Penned specifically for Frank by Sammy Cahn and Jule Styne, “The Christmas Waltz” has become a holiday standard, introduced by Sinatra and subsequently covered by countless artists. Sinatra’s warm “Merry Christmas” at the song’s end adds a personal touch.

Side two transitions to traditional carols, where Sinatra, backed by Jenkins’ orchestra and the Ralph Brewster Singers, delivers deeply felt interpretations. His pitch-perfect renditions of classics like “O Little Town of Bethlehem,” “Hark! The Herald Angels Sing,” and “Silent Night” tap into the profound emotions associated with the season. Whether rooted in religious faith or secular appreciation, these performances resonate with spiritual depth. They evoke a sense of peace and reflection, ideal for quiet moments by the fireplace. This album showcases Sinatra’s ability to convey the solemnity and heartfelt sentiment of Christmas, offering pure class and emotional depth. Some earlier, truncated releases omitted the more upbeat tracks, further emphasizing the album’s generally reflective mood.

Reprise Records: Collaborations and Family Festivities

After establishing his own label, Reprise Records, Sinatra continued to release Christmas music, though not another full solo LP. Instead, his Reprise-era holiday output features collaborations and a unique family project.

Album cover for '12 Songs of Christmas' (1964 Reprise Records), a collaborative Frank Sinatra Christmas LP with Bing Crosby and Fred Waring.

12 Songs of Christmas (1964)

This album saw Sinatra team up with fellow icon Bing Crosby and the renowned choral group Fred Waring and The Pennsylvanians. While perhaps less cohesive than his solo efforts, the record contains significant highlights. Frank shines on “An Old-Fashioned Christmas,” a poignant Cahn/Van Heusen composition exploring themes of nostalgia and longing for simpler times. The lyrics paint a picture of someone successful in the modern world (“steel and chrome”) yearning for the warmth and tradition of Christmases past, beautifully capturing a universal sentiment. Sinatra also joins Crosby for spirited duets on “Go Tell It on the Mountain” and the joyful “We Wish You the Merriest.”

Promotional photo for 'The Sinatra Family Wish You a Merry Christmas' (1968 Reprise Records), showing Frank with Tina, Nancy, and Frank Jr.

The Sinatra Family Wish You a Merry Christmas (1968)

Four years later, Frank gathered his children – Nancy, Frank Jr., and Tina – for a family Christmas album. Cahn and Van Heusen contributed the lighthearted opener, “I Wouldn’t Trade Christmas.” A standout track is Nancy Sinatra’s evocative performance of “It’s Such a Lonely Time of Year,” written by Chip Taylor (known for “Wild Thing” and brother of actor Jon Voight). It’s a melancholic yet beautifully crafted song. Frank introduces another holiday gem, Jimmy Webb’s “Whatever Happened to Christmas?”, revisits “The Christmas Waltz,” and the entire family joins in for a unique rendition of “The Twelve Days of Christmas.” While uneven due to the shared vocal duties, the album offers a charming and personal glimpse into the Sinatra family’s holiday spirit.

Frank Sinatra and his children (Nancy, Frank Jr., Tina) in the recording studio for their 1968 family Christmas LP.

Later Releases and Legacy

For those seeking a compilation of Sinatra’s Reprise-era Christmas work, the 1994 CD The Sinatra Christmas Album is a valuable collection. It gathers Frank’s tracks from the 12 Songs of Christmas and The Sinatra Family albums, along with two later singles. “A Baby Just Like You” (written by John Denver) and particularly “Christmas Memories,” both released in 1975, are gentle, heartfelt additions to his Christmas discography, continuing the reflective tone.

Frank Sinatra smiling warmly, seated beside a decorated Christmas tree, embodying the classic holiday spirit associated with his festive LPs.

Ultimately, the Frank Sinatra Christmas LP collection offers a rich tapestry of holiday moods, weighted towards elegance, warmth, and introspection. While not the non-stop swinging party some might expect, Sinatra chose to emphasize the nostalgic, reverent, and often poignant aspects of the season. His recordings capture the feeling of quiet reflection, the warmth of family, and the enduring power of traditional carols. These albums provide a sophisticated and deeply felt soundtrack, perfect for savoring the fleeting, cherished moments of peace and togetherness that define the Christmas spirit. They stand as timeless additions to any holiday music library, showcasing a different, yet equally compelling, side of the legendary performer.