Harry Connick, Jr. Rankings And Opinions

If you’ve ever tried to describe Harry Connick, Jr. in one sentence, you’ve probably failed. Is he a jazz prodigy from New Orleans? A big-band crooner? A Hallmark-movie heartthrob? A Broadway composer? A Super Bowl hype man? The answer is: yes. All of the above. And that’s exactly what makes ranking Harry Connick, Jr.’s work such a fun (and slightly impossible) project.

Below, we’ll break down Connick’s career into categoriesalbums, songs, movies, and TV momentspulling from fan favorites, critic rankings, and streaming data to build a thoughtful, opinionated look at his legacy. Think of this less as a definitive list and more as a lovingly argued guide for anyone who wants to dive deeper into all things Harry.

Why Harry Connick, Jr. Is So Hard to Rank

Before we get into the rankings, it helps to understand just how broad Connick’s career really is. Born in New Orleans in 1967, he started performing on piano as a child and was recording with local jazz bands by age ten. He studied at the New Orleans Center for Creative Arts and later in New York, where a Columbia Records executive signed him and launched his recording career.

Since then, he has released dozens of albums covering New Orleans jazz, big-band swing, standards, funk, romantic ballads, and Christmas music. He’s won three Grammy Awards, two Emmy Awards, and holds a record number of No. 1 albums on the Billboard jazz charts. Oh, and he’s also starred in hit films like Independence Day, Hope Floats, and The Iron Giant, as well as Broadway productions and his own daytime talk show.

So when we talk about “the best” of Harry Connick, Jr., we’re talking about overlapping careers: recording artist, bandleader, entertainer, actor, and hometown ambassador for New Orleans. With that in mind, let’s rank what most fans and critics consider his standout workstarting with the albums that defined his sound.

Top Harry Connick, Jr. Albums: Ranked

Album rankings blend sales numbers, critical response, fan voting, and cultural impact. Sites that track best albums and jazz discographies often highlight a similar core group of titles, with some variance based on whether you lean jazz purist or pop-friendly listener.

1. When Harry Met Sally… (1989)

This soundtrack is where many fans first met Connick’s voice. His interpretations of Great American Songbook standards“It Had to Be You,” “A Wink and a Smile,” “But Not for Me”helped define the film’s romantic mood and turned him into a mainstream star. Critics praised the album for its lush arrangements and classic big-band feel, while jazz fans appreciated that he brought a young, virtuosic swing sensibility to songs that could easily have felt overfamiliar.

2. We Are in Love (1990)

If the soundtrack proved he could handle standards, We Are in Love showed he could also write new songs that felt timeless. The title track became one of his signature tunes, and the album won him a Grammy for Best Jazz Vocal Performance. It’s often ranked among his top albums because it perfectly balances big-band energy with modern polish.

3. When My Heart Finds Christmas (1993)

Love it or complain that it plays in every department store from November oneither way, you can’t ignore this one. When My Heart Finds Christmas is his best-selling album in the United States and one of the top Christmas albums of the SoundScan era. It blends originals with standards, and his crooner style is tailor-made for holiday nostalgia. In many households, this album basically is December.

4. Only You (2004)

Connick’s highest-charting release, Only You reached the top five in the U.S. and U.K. with its collection of 1950s and 1960s ballads. The arrangements are sleek and romantic, and it’s a go-to recommendation for anyone who likes his voice but isn’t sure where to start. It also cemented his reputation for giving standards a modern, approachable sheen.

5. She (1994)

This is the curveball. She is a New Orleans funk album, and when it came out, some jazz fans were deeply confused. Critics and discography sites still flag it as a key turning point: Connick embraced brass-heavy grooves and a looser, more playful style that echoed his hometown’s club scene. Today, it’s often ranked high by fans who love his willingness to experiment.

6. Alone With My Faith (2021)

Recorded largely during the COVID-19 lockdown, this album finds Connick playing every instrument, arranging every track, and leaning into spiritual themes. It earned a Grammy nomination for Best Roots Gospel Album and gets strong critical respect for its introspective tone and DIY approach. It may not be his most commercial album, but in terms of artistry, it ranks surprisingly high.

Honorable mentions go to Blue Light, Red Light, Come By Me, and Songs I Heard, all of which pop up repeatedly in jazz-focused rankings and fan lists.

Best Harry Connick, Jr. Songs: Fan Favorites and Deep Cuts

Song rankings for Connick can be sorted in a few ways: chart performance, streaming numbers, and fan votes. Sites that track his top tracks or “best songs” lists tend to repeat a familiar core.

1. “It Had to Be You”

This is Connick’s calling cardthe big-band vocal version from When Harry Met Sally… and the trio instrumental both rank near the top on curated song lists and streaming charts. It’s romantic, swingy, and just a little dramatic, which sums up his appeal nicely.

2. “A Wink and a Smile”

Another When Harry Met Sally… favorite, this track shows off his smooth phrasing and light, playful swing. It regularly appears in “best of” lists and has become a first-dance favorite for couples who want something classic but not overplayed.

3. “We Are in Love”

The title song from his Grammy-winning album still gets plenty of respect from critics and fans. It’s a modern standard, with a melody that feels like it could’ve been written in the 1940s but lyrics that land as timeless rather than dated.

4. “Recipe for Love”

Catchy, lighthearted, and endlessly charming, “Recipe for Love” scores highly on fan-driven rankings and chart retrospectives. It captures the playful side of Connick’s personahalf big-band showman, half guy-next-door who just happens to be able to scat.

5. “Autumn in New York”

This standard is one of Connick’s most-streamed tracks and a favorite on jazz playlists. His version is moody and cinematic, leaning into the romance of both the song and his long relationship with New York as a young musician.

6. “I Pray on Christmas” & Other Holiday Hits

Holiday songs like “I Pray on Christmas,” “What Are You Doing New Year’s Eve?” and “The Christmas Waltz” consistently appear among his top-streamed tracks. Love them or try to escape them at the mall, they’re a huge part of why his name is so familiar to casual listeners.

Harry Connick, Jr. on Screen: Movies and TV Moments

Connick’s acting career tends to surprise people who only know him as the guy singing jazz on a stool. But his filmography is long and eclectic, with roles in war movies, thrillers, animated films, and cozy romantic comedies.

Top Movie Performances (Ranked)

1. The Iron Giant (1999) – In fan-driven movie rankings, this animated cult classic almost always lands near the top. Connick voices Dean, the beatnik artist with a heart of gold, and brings a relaxed, wry charm that fits perfectly with the film’s gentle, emotional tone.
2. Hope Floats (1998) – As Justin, the quiet, patient love interest opposite Sandra Bullock, Connick leans fully into the romantic-lead role. This one tends to rank high both with fans of ’90s rom-coms and in curated “best Connick films” lists.
3. Independence Day (1996) – He doesn’t have a huge amount of screen time as hotshot pilot Jimmy Wilder, but he’s memorable enough that fans still bring him up whenever they revisit the movie. It’s one of his most widely seen roles.
4. Copycat (1995) – Here, Connick goes dark as a chilling serial killer in this thriller. Critics and ranking lists often highlight this performance as proof that he’s more than just a charming croonerhe can be genuinely unsettling when he wants to be.
5. Dolphin Tale (2011) & Dolphin Tale 2 (2014) – As Dr. Clay Haskett, Connick anchors these family films with warmth and sincerity. They regularly show up in “best of” lists for his later career.

On television, he’s known for his recurring role on Will & Grace, his stint as a judge on American Idol, and his own daytime talk show Harry, which allowed him to lean into his natural charisma and musical talent in front of a live studio audience. More recently, he’s appeared as a judge on international talent shows and continues to show up in live TV specials.

The New Orleans Factor: Why His Hometown Matters

Any attempt to rank Harry Connick, Jr. that ignores New Orleans is missing the point. His music, stage presence, and even his public persona are steeped in the rhythms and culture of the Crescent City. Official bios and orchestral profiles emphasize how deeply his sound is rooted in New Orleans jazz traditions, gospel influences, and the city’s unique blend of joy and melancholy.

In 2025, he opened the Super Bowl broadcast in his hometown, welcoming viewers with a big New Orleans-themed pre-game performancebrass bands, Mardi Gras flavor, the works. It was the perfect reminder that, no matter how many Hollywood roles or Broadway shows he takes on, he’s still deeply identified with his home city.

Current Legacy: How Fans and Critics See Him Now

So where does Harry Connick, Jr. rank in the broader world of entertainers? Biographical overviews and critic profiles typically describe him as one of the most successful jazz-influenced popular vocalists of his generation, noting his Grammy and Emmy wins, multi-platinum albums, and long-running work across stage and screen.

Yet fan opinions are a bit more personaland more fun. For many listeners, he’s the voice of cozy holiday shopping trips and rom-com movie nights. For jazz fans, he’s a technically gifted pianist who brought traditional swing into the late 20th century mainstream. For movie lovers, he’s either the sweet guy in Hope Floats or the guy who made them weirdly nervous in Copycat. And for New Orleanians, he’s the hometown kid who never stopped representing the city on the world stage.

If you’re building your own “Best of Harry Connick, Jr.” playlist or movie marathon, these rankings are a great starting pointbut the real fun is in discovering which era or style of his work you connect with most.

Personal-Style Experiences and Opinions on Harry Connick, Jr.

To really understand why people care enough to debate Harry Connick, Jr. rankings, it helps to zoom in on the small, human-scale experiences fans tend to have with his work.

1. The “Holiday Soundtrack of My Life” Effect

Ask around and you’ll quickly find people who don’t think of Connick as “a jazz artist” so much as “the guy we put on when we decorate the tree.” His Christmas albums have become a yearly ritual: you pull out the lights, someone plugs in the speakers, and suddenly his voice is woven into your family’s traditions. Even if you aren’t trying to be sentimental, it happens anyway. That emotional association is part of why his holiday tracks rank so highly in streams and playlistsstreaming data is just a fancy way of measuring how often we repeat our favorite feelings.

2. The Gateway to Jazz for Non-Jazz People

Another common experience: Connick becomes someone’s first step into jazz. Maybe they discovered him through a movie soundtrack or a romantic playlist, then realized they actually like swing rhythms and big-band horns. From there, it’s a short hop to classic artists like Frank Sinatra, Ella Fitzgerald, or Louis Armstrong. In that sense, his music serves as an approachable bridge between pop and more traditional jazzsmooth enough for casual listening, but with enough rhythmic and harmonic detail that serious listeners can dig into it too.

Fans also talk about how approachable his live performances feel. He jokes with the audience, riffs on the piano, and is just as likely to crack a self-deprecating line as he is to hit a perfectly placed high note. That “regular guy with ridiculous talent” persona is a big part of why his concerts stand out in people’s memories.

3. Comfort Movies and Quiet Re-Watches

On the film side, people often rank their favorite Connick performances less on strict critical criteria and more on comfort. Maybe they rewatch Hope Floats when life feels messy, or throw on Dolphin Tale with kids because they want something warm and wholesome. Or they rediscover The Iron Giant and realize, “Oh right, that’s Harry Connick, Jr. as Dean.”

These movies aren’t just titles on a listthey become emotional markers. When fans vote on his “best” film roles, they’re often really voting for which version of themselves they remember being when they first saw him on screen: the teenager watching a summer blockbuster, the parent watching a family movie, or the late-night viewer surprised by how intense he is in a thriller.

4. New Orleans Pride and Representation

For people from New Orleans, there’s an extra layer of pride in Connick’s success. They see a hometown musician who didn’t sand off his roots to fit into a generic Hollywood mold. When he opened the Super Bowl broadcast in 2025 with a full New Orleans musical celebration, it felt less like a gig and more like a city-wide shout-out.

That sense of representation matters. It’s one more reason many fans rank his live New Orleans-themed performancesor his big-band concerts that lean heavily on Crescent City rhythmsat the top of their personal lists.

5. A Career That Keeps Evolving

Finally, there’s the simple fact that Connick hasn’t stopped creating. Whether it’s new albums that explore his faith, upcoming compositions for Carnegie Hall, or continued work on stage and screen, he’s clearly not interested in coasting on past hits. For fans, that creates an ongoing, open-ended ranking project: every new release has the potential to shuffle the list.

In the end, Harry Connick, Jr. rankings and opinions tell us as much about the people doing the ranking as they do about the man himself. Some of us will always start with When Harry Met Sally…. Others will swear his funk period is underrated. Some will cling to the Christmas albums like a sonic security blanket. And that’s the fun of it: with a career this varied, there’s room for everyone’s list to be right.

Conclusion

Trying to rank Harry Connick, Jr. is a bit like trying to rank New Orleans dishessure, you can make a list, but you’re really just celebrating the variety. From Grammy-winning jazz albums and endlessly replayed holiday classics to memorable movie roles and hometown-proud live performances, his career offers multiple entry points for fans with different tastes.

Whether you’re here to argue that We Are in Love should outrank Only You, to defend the greatness of Hope Floats, or to admit that your entire relationship with his work is “I just love the Christmas stuff,” there’s no wrong way to build your personal Harry Connick, Jr. ranking. The important part is that you hit play, revisit the highlights, and maybe discover a few deep cuts along the way.