Harry for the Holidays: The Christmas Music of Harry Connick, Jr.

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I discovered vocal jazz in the winter of 1996 when I was 24. Now, when I say “vocal jazz”, I’m referring to a lot of things. To make it easy for the uninitiated, I always say “Frank Sinatra and Friends”. What I really mean is singers like Sinatra and Bennett, yes, but also lounge music, easy listening and all purveyors of the Great American Songbook; from Dinah Shore to Jimmy McGriff. Before this big discovery, all I owned of this idiom was one cassette of an old Columbia Records Frank box set, the soundtrack from the Thelonious Monk film Straight No Chaser and Harry Connick’s first true vocal album, 1990’s We Are in Love.

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During Christmas of that year of ’96, I was inspired to seek out Harry’s first Christmas album, 1993’s When My Heart Finds Christmas, the thinking being of course that Harry would put out a proper, swinging, old school-type Christmas record that I would like. I wasn’t wrong.

There’s an intangible with Christmas records by “pop” artists. Some artists can easily convey the true affection they genuinely feel for the season, while others give you the impression that there is a more monetary motive for releasing a “holiday” album. In the case of the singers of old, it feels authentic. Values and morals, of course, were different back then and many performers felt a need to mark each season by recording carols or contemporary Christmas music often coupled with a Christmas-themed television or radio special. Some artists, like Jimmy Durante, Fred Astaire and Burl Ives, lent their talents to children’s animated TV programs.

The thing about the golden era of Christmas music is that it was golden; the majority of the Christmas songs we cherish today and listen to every year came out in the first half of the 20th century. Since then people who have attempted to add new songs to the canon have met with varying degrees of success. In 1990, one of the greatest purveyors of Christmas music the world has ever known, Andy Williams, recorded a song he predicted would become a standard, “Christmas Needs Love to Be Christmas”. Ever heard of it? Didn’t think so. On the other hand, in 1994, Mariah Carey released “All I Want for Christmas is You”, a song she co-wrote with her producer, Walter Afanasieff. This song has been called “one of the few worthy modern additions to the holiday canon” and sold 16 million copies, making it the 12th best-selling single of all-time. It’s the biggest-selling Christmas song by a female and has earned $60 million in royalties.

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But back to Harry. Many people initially thought of Connick as a throw-back to a previous time. He broke out at the age of 22 with his music for the film When Harry Met Sally…, a soundtrack comprised of standards (including a great instrumental “Winter Wonderland”). It didn’t take long for him to make his first Christmas album and he has gone on to release four Christmas albums, an animated TV special and a Christmas concert program. Connick’s album releases and film performances have seen him operate across a wide spectrum. He has never allowed himself to be pigeon-holed as a “retro crooning guy” but, as we will see, his work in the field of Christmas media does link him with the singers of the middle of the 20th century.

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When My Heart Finds Christmas (1993) — As I said at the outset, this is where I came in. In many ways. In my early days of exploring the jazz vocal idiom (read about my discovery here), I was listening to Harry Connick and also the Brian Setzer Orchestra, two artists who have applied their swingin’ sound to the Christmas season. Harry’s first Christmas album is one of the finest Christmas records released in the modern era. An infinitely accessible album, this record was the best-selling Christmas record of ’93, is the 12th best-selling Christmas album released since 1991 and is Harry’s best-selling album, reaching #13 Pop its year of release. But more than numbers, Harry gets so many things right with this album.

It is such a gamble trying to sell to the public a new Christmas song. Connick secures his place in the Christmas music pantheon with the original songs on When My Heart Finds Christmas. He wisely positions the mellow title track second, after an energetic opener. “In my eyes are valentines and Easter eggs and new year’s wines. But when my heart finds Christmas my eyes will shine like new”. With this wonderful song, Harry expresses his sincerity and shows off his immense skill as a crafter of song; his full talents as composer, orchestrator and vocalist are on display. Listen for the dramatic piano smears and building orchestra when he takes it up a key for the finale: “My heart told me once before…” This may be the finest, classiest song he has ever written. (How have I never seen this video?!)

Get a musicologist in here and he or she could not accurately describe to you the joyous “(It Must’ve Been Ol’) Santa Claus”. The appeal of this song is intangible and is all feel and groove. Connick applies the sound of his native New Orleans to this track courtesy of legendary drummer Joseph “Zigaboo” Modeliste of the Meters. And if a hallmark of an enduring Christmas song is your ability to song along, then this track is built to last. “Santa Claus, Santa Claus, it must’ve been old Santa Claus…” 

“The Blessed Dawn of Christmas Day” gives you an indication of Harry’s upbringing and where his heart is at. A practicing Roman Catholic, Connick considers Christmas to be a celebration of the birth of Jesus Christ. This original song is reverent and very stylish. Again, his considerable composition and orchestration talents are on full display.

Combining the different moods of the two previous songs is “I Pray on Christmas”. A great gospel workout, this tune features sparkling piano playing by Connick and a spirited group vocal. Seek out an interesting version of this song by venerable gospel singers the Blind Boys of Alabama featuring the great Solomon Burke.

Added to these originals are great big band treatments of some Christmas classics. The “Sleigh Ride” that starts the record stands with any other version of this timeless tune. Same with “Let It Snow! Let It Snow! Let It Snow!”. “Christmas Dreaming” is wonderful and I’d like an orchestrator to listen to Harry’s treatment of the venerable “O Holy Night”. The orchestral sound of this track is sumptuous and is incredibly erudite.

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Harry for the Holidays (2003) — Ten years later came another great Christmas record from Harry, this one decidedly N’Awlins in flavour. Less orchestral and more big band, Harry for the Holidays has a great sound to it and features some of Harry’s best Christmas music.

Originals include “The Happy Elf” and here is where Harry links himself with Christmas entertainers of the past. This is a song about one of Santa’s elves, the excitable Eubie, who loves working in the workshop. “The Happy Elf” became an animated TV special of the same name that was Harry’s nod to the classic Rankin/Bass Christmas specials. Harry narrates as Little Farley and other characters are voiced by Carol Kane, Lewis Black and, in a sublime piece of casting, Mickey Rooney as Santa. Connick’s Christian views are apparent again in the stirring song “I Come With Love” which depicts the life of Jesus Christ; “I come with love to worship and honour my Father above”. Both “The Happy Elf” and “I’m Gonna Be the First One” are indications that this is the first Christmas record Harry Connick released since becoming a father. The latter is a song of the joy a child feels on Christmas morning.

Among his best seasonal recordings stands “Nothin’ New for New Year”. Perhaps surprising from Connick, this is a duet with country music legend, George Jones, a singer Harry referred to as one of his favourites. “Nothin’ New” is a wonderful, emotional song.

Harry flexes his muscle as an arranger on Harry for the Holidays, providing intriguing settings for “Silver Bells” and “I’ll Be Home for Christmas”. But here’s where Harry can lose me; OK, challenge me. His inscrutable chart for “O Little Town of Bethlehem” leaves you scratching your head. The lyrics he’s singing and the song as we generally hear it seem to have little in common with what he has the orchestra doing.

Harry’s versions of “Frosty the Snowman” and “Santa Claus is Coming to Town” are straight-up Bourbon Street parades but the “Silent Night” that closes the record is like nothing you’ve ever heard. Highlighting the stunning work of trumpeter and frequent Connick collaborator Leroy Jones, this 200 year old song gets a heartfelt gospel workout from the boy from New Orleans. Like Harry’s first Christmas record, Harry for the Holidays was the biggest-selling record of the season. It was accompanied by a television Christmas special that featured a live performance from Harry and orchestra that featured appearances by Marc Anthony and Nathan Lane. The DVD has great interviews and outtakes of charismatic Harry cutting up with his band. In the interviews he talks about the songs on the record, how some of them feature the great fictional characters of Christmas while other songs, Harry says, are “about Jesus Christ. Which is what Christmas is about”. He also discusses how his wife told him he was doing Donny Hathaway’s “This Christmas” on the record. When Harry waffled, his wife said “Let me make myself clear; you’re DOING ‘This Christmas’ on the record”.

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What a Night! A Christmas Album (2008) — Perhaps the least successful of Harry Connick, Jr.’s vocal Christmas albums, What a Night! still contains some good tunes – and one stunning performance that ranks among the best songs he has recorded. Where this record falls short of the others is in the originals; which is not surprising. After all, how many great Christmas songs can a modern artist add to the canon? By this point, Harry had already delivered quite a few.

The title track is certainly clever but I wonder if it’s not one of those arrangements of Harry’s that is obviously inventive but perhaps not as accessible as it could be. The lyrics many of us can relate to; “better hurry, grandma starts to worry. She thinks ev’ry flurry turns into a storm”. “Christmas Day” is earnest and heartfelt and I give points for that. It is a pleasant but uninspiring song. Harry duets with a frequent collaborator at this time, Kim Burrell on the original closer “Song for the Hopeful”. There’s a strong sentiment here in this song of faith and hope but Kim’s vocal gymnastics don’t add anything to a rather laborious number.

Harry does well on the classic “Please Come Home for Christmas” and “It’s Beginning to Look a Lot like Christmas” is about as straight forward as Harry gets on this album. When I first heard Harry’s “O Come All Ye Faithful”, however, it felt like walking in shoes that were on the wrong feet. This is the song I cite when making the claim that Harry’s arrangements, while definitely ornate, can be very hard to relate to. This tune in Harry’s capable hands is stunning but the familiar melody of this carol is virtually unrecognizable. Even in the bridge when the strings state a familiar theme, there are piano fills draped over top as camouflage almost. Which brings me to “We Three Kings”. One half Professor Longhair and one half James Bond, Harry’s version of this carol is an energetic aural feast. His piano playing is full-bodied and exciting and the horn arrangement is absolutely stunning. This recording is glorious. In all seriousness, I am sometimes brought to tears by beautiful music but never by an uptempo song like Harry’s “We Three Kings” but I have wept listening to this. It is overwhelming in its magnificence.

Added to these three albums are two sets of mostly instrumental music from Harry’s animated Christmas show The Happy Elf (2011). Here’s where Connick cements his credentials alongside other greats; having a Rankin/Bass-inspired program on his CV certainly increases his Christmas rep. The Happy Elf is narrated by Connick and features some pretty good music. The show is charming and the two albums are Music from “The Happy Elf”: Connick on Piano, Volume 4 and the free soundtrack disc that accompanied some of the DVD releases. Now, I’m no music critic and I’m certainly not a jazz music critic but Harry Connick, Jr.’s reputation as a jazz artist is formidable. However, I’ve always conjectured that he does not get the love he deserves in the jazz community due to the fact that he is not jazz through-and-though and purists don’t like that. The music from The Happy Elf is fine; it’s just not very Christmasey. It’s nigh on impossible, says I, to conjure up a Christmas feeling with instrumental jazz originals. This brings to mind my main man Ramsey Lewis and his trio’s second album of Christmas music featuring great originals that aren’t exactly imbued with the spirit of the season just because Ramsey gives them names like “Egg Nog” and “Plum Puddin'”.

The important thing about The Happy Elf, though, is the fact that it exists. It illustrates the importance Harry puts on the season and it speaks to the many things he has to say about Christmas. And you can’t deny the fact that The Happy Elf – Bing Crosby and Rankin/Bass are thanked in the credits of the TV program – link Harry with the Fred’s and the Burl’s of old.


It seems to me then that Harry Connick’s three main Christmas albums land in three separate sub genres that Connick is well-versed in. When My Heart Finds Christmas is a crowd-pleasing big band/vocal album, Harry for the Holidays deals in the New Orleans sound with some pop music leanings and What a Night! is steeped in jazz. The 45 songs on these three albums comprise all of what we expect from Christmas music and give a listener everything, really. There are finger-popping arrangements of classic holiday songs, reverent carols with magnificent orchestral backgrounds, a plethora of original songs, all sincere and well-intentioned and most of them excellent and plenty of tunes for children. This all adds up to an impressive canon and a wonderful Christmas gift from Harry Connick, Jr. to all of us.

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