Frank Sinatra and Christmas go together like hot cocoa and marshmallows. During his time in the music industry, Ol' Blue Eyes managed to produce an abundance of holiday tunes. He released two holiday albums in the 40s and 50s (Christmas Songs by Sinatra and A Jolly Christmas From Frank Sinatra) and then once the 90s rolled around, we got lots of Sinatra Christmas compilation albums.

Besides Bing Crosby, the guy is essentially the voice of the season. Looking to put together a Sinatra holiday playlist? Or perhaps you're curious to know what his biggest and best Christmas songs are? Below are the 10 Sinatra holiday songs you don't want to skip out on this December!

1. "Jingle Bells"

We love those J-I-N-G-L-E bells! This Yuletide classic, written by New England songwriter James Pierpont, was exactly 100 years old when Sinatra recorded it as the opening track to his 1957 record A Jolly Christmas From Frank Sinatra. The Ralph Brewster singers really give their all in this, and Sinatra even responds in playful call-and-response with them.

The arrangement in Sinatra's "Jingle Bells" is particularly dynamic. It's mostly a chipper swing number with a mix of Ralph Brewster singer fun and deep Sinatra vocals. But in the instrumental bridge, you also get some plucky string action. We would say this is one of Sinatra's most popular holiday tunes. Oh what fun it is to put this sleigh ride on replay!

2. "Have Yourself A Merry Little Christmas"

This cover of Judy Garland's 1944 song from the MGM musical Meet Me in St. Louis is certainly less somber. It's radiant with those soprano choral sounds, shimmering strings, and the Bing Crosby-esque delivery from Sinatra.

Sinatra first tackled "Have Yourself A Merry Little Christmas" in 1948, but, nine years later, he recorded what’s regarded as his definitive take on the song. "Have Yourself A Merry Little Christmas" is considered an evergreen holiday tune, but Sinatra's rendition of this is hailed as the best there is.

3. "Santa Claus is Comin' to Town"

Our personal favorite Christmas Sinatra tune! Sinatra gave this J Fred Coots and Haven Gillespie number the big band swing it needed. This version of the 1934 tune was arranged by Axel Stordahl and was properly released as a single in 1948.

Want to know something odd about this cover? "Santa Claus is Coming to Town" was actually recorded three days after Christmas, on December 28, 1947. Sinatra updated it ten years later but kept the swing elements on a version performed on his TV special with Bing Crosby.

4. "Mistletoe and Holly"

Oh, by gosh, by golly! This is an original Sinatra holiday tune, and one we feel is slightly overlooked in his catalogue! "Mistletoe and Holly" was released in 1957 and was co-written by Sinatra, Dok Stanford, and Hank Sanicola. It gained some recognition in 1960 for being used as the theme song for the Christmas Seals appeal. There's also a remix of "Mistletoe and Holly" by Kaskade!

Besides Sinatra's standout vocals, this song features opening pizzicato strings, contributions from American composer and pianist Gordon Jenkins, and twinkling background vocals by the Ralph Brewster singers.

5. "White Christmas"

The perfect song to play when it's snowing out. So merry and bright! Frank Sinatra's "White Christmas" was a small commercial success back in its day. Sinatra recorded this Irving Berlin classic with an orchestra and choir (The Bobby Tucker Singers) in 1944. Arranged by Alex Stordahl, it reached #7 in the US pop charts and charted again in 1945 and 1946.

Sinatra also recorded a version of "White Christmas" for Capitol, with Nelson Riddle at the helm. He duetted his version of the song with Bing Crosby on the 1957 US TV special Happy Holidays With Bing And Frank.

6. "Silent Night"

Yes, Sinatra's covered some old carols, too. "Silent Night" – a hymn of Austrian origin – goes back to 1818, when it was composed by Franz Gruber and Joseph Mohr. It landed into the commercial Christmas music sphere in 1935, when Bing Crosby had his rendition land on the Top 10 of the US charts.

Sinatra recorded his version as a Christmas single in 1945, and it later appeared on his album A Jolly Christmas From Frank Sinatra. He manages to get out some powerful notes in his cover while still being soothing enough to keep the baby sleeping in heavenly peace.

7. "I'll Be Home For Christmas (If Only In My Dreams)"

When you first hear "I'll Be Home For Christmas," you may think it's actually "Silent Night" with the melody of that humming. But bell tolls and laid-back vocals from Sinatra eventually signal a twist; your home won't be so quiet this year...he'll be with you for the holidays!

Sinatra’s slow and slightly somber version of this song was written by Kim Gannon and Walter Kent. They wanted to focus public attention on the plight of soldiers serving overseas during the holiday season. “I’ll Be Home For Christmas” was first recorded by Bing Crosby in 1943. Sinatra makes it his own with a sensitive delivery and underlying hopefulness.

8. "The Christmas Waltz"

Sinatra's take on "The Christmas Waltz" is pure whimsy. There's some holly jolly harmonies from The Ralph Brewster Singers, and Sinatra's vocals sound proud and unshakeable over that three-quarter time.

"The Christmas Waltz" was originally penned by Jule Styne and Sammy Cahn. Sinatra’s longtime musical pal Nelson Riddle is the arranger/conductor here, and the song appeared on A Jolly Christmas From Frank Sinatra. Sinatra revisited the tune on 1968’s The Sinatra Family Wish You A Merry Christmas, featuring The Jimmy Joyce Singers And Orchestra.

9. "Let It Snow! Let It Snow! Let It Snow!"

A swingin' rendition of a classic holiday tune with some big action from the horn section! Sinatra's "Let It Snow! Let It Snow! Let It Snow!" is far from frightful and extremely delightful. It was organized by New York-based trumpeter Axel Stordahl, who was Sinatra’s preferred arranger in the late 40s and early 50s.

The original "Let It Snow!" was written by Sammy Cahn-Jule in July 1945 during a heatwave in Los Angeles. Sinatra recorded his cover of it five years later, releasing it as a Christmas single.

10. "The Christmas Song (feat. Nat King Cole)"

While this is actually a duet between Sinatra and Nat King Cole (the original version of this song is by King Cole), it's still poignant enough to include on this list. Co-written by singer Mel Tormé in 1945, “The Christmas Song” was a massive US hit for Nat King Cole in 1946 and has been much covered since. Soft and dreamy, this arrangement of the tune perfectly balances out King Cole's bright notes with Sinatra's deep swagger.

Sinatra’s 1957 recording of this duet is notable because arranger Gordon Jenkins works in a quote from “Jingle Bells,” played by pizzicato strings. Like on many other Sinatra holiday songs, the Ralph Brewster Singers provide soft background vocals.

Check out our selection of free stations streaming Frank Sinatra music at Live365.com

_{Ready to start your own station? Contact one of our Product Consultants or visit our website today. Keep up with the latest news by following us on Facebook (Live365 (Official) and Live365 Broadcasting) and Twitter (@Live365 and @Broadcast365)! You can also shop Live365 swag and branded merchandise at store.live365.com.}

_{Article Image: The cover and vinyl record of Frank Sinatra's album, "Christmas Songs by Sinatra." (Stefano Chiacchiarini '74 via Shutterstock.)}