“He’s the closest to Louis Armstrong that I’ve ever heard,” Doc Cheatham used to say of Nicholas Payton, and anyone who’s experienced Payton’s wondrously expressive trumpeting—equally explosive in a modern mode or in early New Orleans style—has to appreciate the truth in that statement.

And so it’s more than fitting that the 27-year-old Payton, the greatest New Orleans trumpeter of his generation, would release Dear Louis in this, the centennial of Armstrong’s birth. The record is a prodigious musical love letter to the greatest trumpeter/performer in jazz history and the immortal spiritual Buddha of New Orleans music. And Payton applies plenty of postage in his attempt to get this bulky letter to its far-flung destination: musical paradise, where we know Louis Armstrong (a.k.a. “Satchmo” or “Pops”) currently resides.

As usual, Payton set the bar extremely high for himself. “What I’m trying to do is not only depict what Louis Armstrong did, but all that has come over the last hundred years as a direct result of his influence. He’s just as significant today as he was 50 years ago,” he said in a recent interview.

Tackling Armstrong’s legacy is a lot like tackling all of jazz history, an overwhelming task to say the least. To accomplish this feat, Payton enlists a stellar 11-piece big band (as well as organist Melvin Rhyne and guest vocalists Dr. John and Dianne Reeves on a few tracks), opening up a vast array of textural and dynamic possibilities. Compositionally, he reinvents a wide spectrum of Armstrong material with expansive modern arrangements, an approach similar to that employed on his breakthrough 1996 recording, Gumbo Nouveau (which reinvented classic New Orleans material), but on a much larger scale.

These innovative departures will ruffle purists’ feathers in some cases, and in others come as welcome relief. Take “Hello Dolly,” for example. When he announced this number (long considered the cheesiest of the commercial show tunes from Armstrong’s latter period) at the North Sea Jazz Fest, Payton says he was greeted with boos and whistles. But he and his large ensemble proceeded to transform the song into a panoramic instrumental masterpiece, with soaring horn charts and diverse percussion effects, evoking the renowned Gil Evans/Miles Davis collaborations and just a touch of mellow bossa-nova and ’70s soul, climaxing, after sharp solos from Tim Warfield on soprano sax and Payton on flugelhorn, with a spicy Kenyatta Simon conga solo.

“Hello Dolly” with a conga solo? It seems almost inconceivable, but Payton makes it work. (Needless to say, the boos gave way to thunderous applause.)

The scope of the other big band arrangements is equally stunning; it’s like a painter extrapolating a massive historical wall mural from a small portrait. Armstrong’s early classic “Potato Head Blues” becomes a snappy swinger with lush orchestration evoking Duke Ellington’s best work. The quirky “Tight Like This” starts dreamily in close proximity to the original, but then segues into an uptempo Latin section punctuated by a scorching Sonny Rollins-esque tenor solo by Warfield, the whole thing suggesting something by Dizzy Gillespie or Eddie Palmieri. Payton plays the famous intro to “West End Blues” with typical head-clearing brilliance, but then the song becomes a grooving shuffle featuring Melvin Rhyne’s organ, the whole band riffing off an exuberant Ray Charles feel.

Particularly refreshing is the pervasive use of tuba (played by Bob Stewart), and not only on the numbers with a pronounced second-line feel, like “I’ll Be Glad When You’re Dead, You Rascal You” and “Tiger Rag,” which Payton imbues with sassy street funk á la the Dirty Dozen. As Payton and anyone who has followed a New Orleans brass band knows, tuba adds a hot bubbling cushion to the “bottom end.”

Ironically, the most poignant big band song is the least complex: “Dear Louis,” the title track and the CD’s only Payton original, a fairly straightforward ballad with glowing harmonies that allows Payton to stretch out in a gorgeous, tender solo.

It’s a little disappointing when the program shrinks down to small band format for the vocal features. Dianne Reeves’ normally gripping voice sounds forced on the awkwardly reharmonized “On the Sunny Side of the Street.” Dr. John fares slightly better on “Mack the Knife.” He’s got one of the world’s most distinctive growls, just as Armstrong had, and his persona would seem perfect to convey the shady-but-lovable gangster character in the song, although Doc seems lackluster compared to Armstrong’s joyous, irresistible charm.

Fortunately, Doc and Reeves manage to make some sparks fly on “Blues in the Night,” a duet in the spirit of the famous Armstrong/Ella Fitzgerald collaborations. But the rapport here seems a little stiff by comparison, missing the infectious flirtation radiating from those old gems.

It’s somewhat surprising when Payton debuts his own vocals on “You Rascal You” and “I’ll Never Be the Same,” a softly swaying Brazilian arrangement. No, he hasn’t been hiding an Aaron Neville or John Boutté-like skill. He’s got a long way to go before his singing equals his trumpet playing, but his voice does convey an endearing sincerity and enthusiasm. In the context of a live show (as when he performed this music live on April 1st at the Mahalia Jackson Theater), his singing seems natural and fun, even exciting, but on a sterile studio recording it appears flat and underdeveloped. Frankly, he needs to “shed” more on this aspect of his musical arsenal.

As for song selection, Payton does an exceptional job spanning the many phases of Armstrong’s career within the limited space (in this case, 13 tracks) allowed by a single CD. Still, it’s unfortunate he couldn’t squeeze in his uptempo big band arrangement of “St. James Infirmary,” one of the highlights of the April 1st performance. With playful stops and starts and explosive drum/horn solos, this arrangement wonderfully evokes the “rejoice when you die” mentality of New Orleans. (Note: Payton says the Japanese Dear Louis includes this track; the domestic release only has a short solo-bass interlude from another version of “St. James Infirmary.”)

In the final analysis, Payton’s masterful playing and big band arrangements provide an extremely rewarding experience, despite the somewhat awkward and distracting forays into undeveloped vocal material. One thing the April 1st show made abundantly clear: in a live setting this material comes to life with great vibrancy. Do not miss the opportunity to hear this extraordinary big band on April 28th at the Fair Grounds!