Let’s be real for a second. If you walked into a smoky jazz club in 1989, you weren't just hearing a piano; you were witnessing a total cultural shift. Harry Connick Jr. wasn't just another singer. He was a phenomenon. When the When Harry Met Sally soundtrack dropped, it basically revived the Great American Songbook for a generation that was currently busy listening to hair metal and synth-pop. He had the jawline, the New Orleans pedigree, and that Sinatra-esque phrasing that made everyone swoon. Naturally, the industry did what the industry does. They went looking for a Harry Connick Jr copycat.
They wanted someone else who could wear a tuxedo without looking like they were going to senior prom.
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But here’s the thing about the music business: it's obsessed with "types." If one guy sells five million records singing "It Had to Be You," every A&R rep from Sunset Boulevard to Broadway wants their own version. Over the last thirty years, we’ve seen a parade of young men with slicked-back hair and a velvet baritone voice being labeled as the "next Harry." Some of them embraced it. Others fought it like crazy.
The blueprint of a Harry Connick Jr copycat
What does it even mean to be a Harry Connick Jr copycat? It’s not just about hitting the notes. It’s a specific cocktail of traits. You need the big band backing, the slightly cocky stage presence, and, most importantly, the ability to bridge the gap between "grandma’s favorite music" and "actually cool."
Connick wasn't just a singer; he was a virtuoso pianist. That’s where most of the so-called copycats fall short. You can teach a guy to swing a lyric, but you can’t easily replicate the decades of New Orleans stride piano that Harry had baked into his fingers since he was a kid studying under James Booker and Ellis Marsalis.
When people talk about copycats in this space, they usually point to guys like Michael Bublé or Peter Cincotti. But calling them copycats is kinda reductive, isn't it? It’s more like they were all drinking from the same well. Bublé, for instance, took the "crooner" archetype and turned it into a global stadium-filling juggernaut. While Harry was leaning into funk, acting in movies like Independence Day, and writing Broadway musicals, Bublé stayed firmly in the lane of the modern standards-bearer.
Why the "Clone" label sticks
It’s about the aesthetic. If you see a guy under a spotlight with a 17-piece brass section, your brain automatically goes to the big names. For a long time, Harry was the name.
Think back to the mid-90s. The swing revival was starting to brew. Bands like Big Bad Voodoo Daddy and the Brian Setzer Orchestra were hitting the charts. Suddenly, every lounge singer in Vegas was trying to mimic that specific New Orleans drawl that Harry made famous. It wasn't just about the music; it was about the brand. The suit. The smirk. The effortlessly cool vibe of a bygone era.
The Michael Bublé comparison: Rival or successor?
You can't talk about a Harry Connick Jr copycat without mentioning Michael Bublé. For years, fans have debated who did it better. In the early 2000s, when Bublé first broke out, the comparisons were constant. Critics were brutal. They called him a manufactured version of what Harry had done organically a decade earlier.
But honestly? That's not fair to either of them.
Bublé leaned much harder into the pop-production side of things. His records were polished to a mirror shine, aimed squarely at adult contemporary radio. Harry, on the other hand, always felt a bit more raw, a bit more "musician's musician." If you listen to Harry’s Blue Light, Red Light album, you hear a guy who is obsessed with the technicality of the arrangements. Bublé is obsessed with the feeling of the hook.
Is Bublé a copycat? Maybe in terms of the business model. He filled the vacuum that opened up when Harry decided to focus more on acting and specialized jazz projects. The market wanted a crooner. Bublé stepped in.
Other names in the "Next Harry" conversation
- Peter Cincotti: He was the young prodigy who actually had the piano chops to back up the comparison. He was 18 when he hit the scene, and the media immediately branded him the heir apparent. He's incredibly talented, but he eventually moved away from the standards to find his own pop-rock identity.
- Jamie Cullum: This guy is a firecracker. While he shares the jazz-piano-vocalist DNA, his energy is way more manic. He’s more likely to jump on top of his piano than to stand behind a stationary mic stand in a tuxedo.
- Seth MacFarlane: Yeah, the Family Guy creator. He’s arguably the most "traditional" of the bunch now. He records at Capitol Studios with the same gear Sinatra used. Is he a copycat? Or just a guy with a massive budget and a deep love for the 1950s?
The New Orleans factor and authenticity
One thing that makes a true Harry Connick Jr copycat almost impossible to find is the New Orleans connection. You can't fake that. Harry grew up in a city where music is literal oxygen. His father was the District Attorney, but his mentors were jazz legends.
When you hear a "copycat" from London or Los Angeles, something is usually missing. It’s the "dirt." New Orleans jazz has a certain grease to it. It’s not polite. It’s loud, it’s syncopated, and it’s slightly behind the beat. Most people trying to emulate Harry’s success focus on the When Harry Met Sally version of him—the clean-cut, romantic lead. They forget about the guy who can play "Big Chief" until your ears bleed.
The trap of the "Standards" genre
The problem with being labeled a copycat in this genre is that the material is all the same. If you sing "Mack the Knife" or "Summer Wind," you are inevitably going to be compared to Sinatra, Bobby Darin, and Harry Connick Jr.
It’s a trap.
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Artists who want to avoid the copycat label have to find a way to modernize the sound without breaking it. Harry did this by writing his own original big band music. He wasn't just covering the classics; he was adding to the canon. Most "copycats" stay in the safe zone of covers because that's what sells at weddings and on Mother's Day.
How the industry manufactures the "type"
Music labels are notoriously risk-averse. They don't want something new; they want "the new version of the thing that worked last year."
In the late 80s, the "Harry Connick Jr type" became a specific casting call. Agencies looked for:
- Square jawlines and "old Hollywood" looks.
- The ability to play at least a little piano.
- A vocal range that stayed comfortably in the baritone/tenor pocket.
- A lack of interest in contemporary trends like grunge or hip-hop.
It’s a narrow lane. When an artist fits that mold, they get pushed into the tuxedo, told to sing Gershwin, and marketed as the "new Harry." It’s often not even the artist's choice. It’s the machine.
Why the "Harry Connick Jr copycat" search exists
People search for this because they miss a specific feeling. Music today is often hyper-digital. It's quantized, autotuned, and built on loops. Harry represents a time when people actually played instruments together in a room.
When someone searches for a "Harry Connick Jr copycat," they aren't necessarily looking for a thief. They’re looking for a vibe. They want that organic, swinging, sophisticated sound that seems to be disappearing from the mainstream.
The evolution of the crooner in the digital age
Today, you don't see as many direct copycats because the "crooner" has moved to social media. You’ll find guys on TikTok who have millions of followers just by singing 30-second clips of "Fly Me to the Moon."
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They have the look. They have the voice. But do they have the career?
Usually, no. Because being a "copycat" is a short-term strategy. You might get a viral hit or a gig at a high-end corporate event, but you won't have the staying power of a Harry Connick Jr. unless you innovate. Harry stayed relevant by pivoting. He did Will & Grace. He was a judge on American Idol. He hosted a talk show. He did Broadway.
The true "copycats" usually fade away because they become parodies of a parody.
Actionable steps for fans and musicians
If you're a fan of this style and you're tired of the same three albums, or if you're a musician trying to navigate this "copycat" minefield, here is how you actually find the good stuff:
- Look for the "Branch-Offs": Instead of searching for people who sound exactly like Harry, look for artists who share his influences. Listen to James Booker or Professor Longhair. That’s where Harry got his "stink" from.
- Check out the New Orleans scene: There are young musicians in the French Quarter right now—guys like Davell Crawford—who carry that same torch but with their own flavor. They aren't copycats; they are part of the same lineage.
- Evaluate the "Why": If you're listening to a new artist and they feel like a Harry Connick Jr copycat, ask yourself: are they bringing anything new to the table? If they are just doing a karaoke version of Blue Light, Red Light, move on.
- Support original "Standards": The genre only stays alive if artists write new songs in that style. Seek out people like Gregory Porter or Cecile McLorin Salvant. They have that classic feel without being clones.
The reality is that Harry Connick Jr. is a bit of a unicorn. He arrived at the perfect moment with the perfect set of skills. You can copy the suit, and you can copy the song list, but you can't copy the soul of New Orleans. Every "copycat" eventually realizes that they’re just standing in a very long shadow. The ones who survive are the ones who eventually step out of the spotlight and find their own light.
Whether it's Michael Bublé's pop-infused stardom or Peter Cincotti's evolution into a singer-songwriter, the "copycat" label is usually just a starting point, not a destination. If you're looking for that specific magic, your best bet is to go straight to the source or look for the artists who are brave enough to break the mold Harry helped build.
The jazz-pop world is big enough for more than one suit-and-tie singer, but there will only ever be one Harry. And that’s probably for the best.
To dive deeper into this sound, start by exploring the discographies of the "New Orleans Piano Kings." Understanding the roots of stride and boogie-woogie will help you distinguish between a talented musician and a mere stylistic imitator. Check out local New Orleans jazz radio stations online to hear the next generation of players who are currently redefining the sound that Harry Connick Jr. brought to the masses decades ago.