Time Capsule: Harry Connick, Jr., When My Heart Finds Christmas

Every Saturday, Paste will be revisiting albums that came out before the magazine was founded in July 2002 and assessing its current cultural relevance. For the season that's in it, we're listening to modern crooner Harry Connick, Jr.'s first holiday album, When My Heart Finds Christmas.

By Clare Martin | December 14, 2024 | 9:00am

Music Reviews Harry Connick Jr.

Time Capsule: Harry Connick, Jr., When My Heart Finds Christmas

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When Christmastime rolls around in the Martin family household, we break out a whole host of CDs (my parents are singlehandedly keeping the industry alive) to mark the occasion. A Charlie Brown Christmas, Bing Crosby, Burl Ives and Michael Bublé are staples in the rotation, but there’s one album I prefer to all the others: When My Heart Finds Christmas, Harry Connick, Jr.’s first holiday LP. I’m hardly alone in the sentiment; the record went triple Platinum in the United States and is his best-selling album here. While I’ve always loved When My Heart Finds Christmas—in particular the boisterous original number “(It Must’ve Been Ol’) Santa Claus”—as a kid I didn’t appreciate just how singularly masterful a musician Connick is.

The New Orleans-raised artist was mentored by legendary jazz and blues keyboardist James Booker (allegedly as part of a deal with Connick’s district attorney father in order to reduce Booker’s sentence) and signed to Columbia Records while still a teenager. He was only 21 when he was tapped for the When Harry Met Sally… soundtrack, which earned him a Grammy Award for Best Jazz Male Vocal Performance. He established himself as a modern crooner well before Bublé came on the scene, carrying the torch of greats like Frank Sinatra and Dean Martin. Besides his musical accolades, Connick has enjoyed a decent acting career as well, with credits including the World War II movie Memphis Belle, The Iron Giant, Will & Grace, Independence Day and P.S. I Love You, to name a few. He even had his own daytime talk show, the succinctly titled Harry, from 2016 to 2018. And who can forget when he changed a bar to get a studio audience clapping on the two and four instead of the one and three. In short, we need to put more respect on Connick’s name.

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Connick was only 25 when he recorded When My Heart Finds Christmas (1993), but the album possesses an assured maturity that makes sense in the context of his early rise to stardom. The fullness and confidence of his sound here feels like it belongs to a much older artist, such is his prodigious talent.

Of the 14 tracks on the album, Connick composed four originals and included six well-known Christmas carols—half of which are religious, half of which are secular. The other four songs—”Ave Maria,” “Parade of the Wooden Soldiers,” “Christmas Dreaming” and “What Are You Doing New Year’s Eve?”—are slightly unconventional picks, making his album stand out from your run-of-the-mill Christmas record that’s just the same old covers.

The first original song is the title track, which starts with dramatic yet dreamy horns and strings that nod at Connick’s cinematic chops. He sings with an unhurried ease, and the lyrics boast a classic simplicity: “All the days are kind to me / But fall too far behind to see / But when my heart finds Christmas / I hope it finds you too.” “When My Heart Finds Christmas” grows triumphant as it continues, embellished by resplendent horns and an angelic choir. It’s not an overtly religious number—especially compared to two of his other original songs, “The Blessed Dawn Of Christmas Day” and “I Pray on Christmas”—other than a passing reference to “Let the angels sing around us.” My personal favorite, “(It Must’ve Been Ol’) Santa Claus,” follows, kicking off with some big old brass and shifting the vibe immediately from reverent peace to joyous tomfoolery. Connick sings from the perspective of a kid who thinks he’s too old to believe in Santa, only for the fat man himself to take our doubtful narrator on an impromptu sleigh ride. From the rambunctious, jazzy piano to Connick’s call-and-response with enthusiastic male singers, this is just one hell of a good time.

Connick’s Catholic faith shines through on “The Blessed Dawn of Christmas Day” and “I Pray on Christmas,” two of his own compositions that nonetheless feel timeless. Swelling, bittersweet strings bring a grandiosity to the former as he sings, “The hearts of sinners reconciled / Amid the ancient morrow mild / Exalt the birth of Mary’s child.” Connick’s velvety voice is so impassioned here that even a heathen like myself can’t help but feel a little awestruck. The gospel number “I Pray on Christmas” invites you to clap along with Connick and his backing singers as easygoing piano traipses through. It’s one of the only original songs on When My Heart Finds Christmas that’s caught on slightly—and I really mean slightly—with The Blind Boys of Alabama and The Oak Ridge Boys recording their own versions.

As for the more traditional Christmas carols, Connick’s takes on “Sleigh Ride” and “Let It Snow! Let It Snow! Let It Snow!” are some of the best thanks to his effortlessly inviting voice and the bombastic use of horns. The soft brush of the drums and lithe strings on “Let It Snow! Let It Snow! Let It Snow!” immediately conjure up images of flurrying flakes. I can’t help but smile every time I hear the blast of brass on that song after he finishes the first line. His rendition of “The Little Drummer Boy” takes advantage of the choir and small army of musicians at his command, but doesn’t necessarily reach the heights of other numbers. “What Child Is This” and “O Holy Night,” though, are sweeping epics. These two tracks tap into one of the most underrated but vital Christmas musical themes: the idea that the holidays can be a little scary, too (think “Carol of the Bells”). The strings sound particularly ominous on both songs, bringing a gravity that makes the Christmas lights twinkle a little brighter in contrast.

Calling the other numbers here off-the-wall choices feels a bit strong, but they’re certainly not top of mind when it comes to Christmas carols. Primarily featuring Connick’s voice and elegant piano playing, his “Ave Maria” is contemplative and somber, reminding all the faithful out there what the true meaning of Christmas is (apparently it’s not eating too much and napping at 2 p.m.). “Parade of the Wooden Soldiers” feels a little kitschy with the evocative toy shop noises at the beginning, but then again, this is Christmas, the season of tinsel and tacky decorations—kitschy is the name of the game. Romantic and gently jazzy, “Christmas Dreaming” and “What Are You Doing New Year’s Eve?” both go down like a well-made cup of cocoa.

The idea of a modern day crooner feels paradoxical, or at the very least like an exercise in nostalgia. Let’s face it—the word cheesy immediately comes to mind. But Christmas may as well be called cheesemas; the two go hand in hand. It’s no wonder, then, that When My Heart Finds Christmas is one of Harry Connick, Jr.’s best albums, a holiday treat that we’re all too happy to revisit each year.

Clare Martin is a cemetery enthusiast and Paste’s associate music editor.