Gothic and poignant, grotesque and sublime, Tom Waits envisages characters and stories through song like a seasoned author does in literature. Before an audience nearing 3,000 on Tuesday night at the Moran Theatre in Jacksonville, Florida – his first-ever appearance in the city – the iconic artist rendered his distinctive creations with a masterful, 27-song performance.

His five-piece band discreetly arced around him, Waits took to a riser at center stage, stomping plumes of dust in the air as he began with “Lucinda,” which segued into “Ain’t Going Down To The Well.” Following a rambunctious “Way Down In The Hole” (propelled by his oldest son, Casey, on drums), he delved into “Falling Down,” his cavernous voice booming at full force.

He tinkers with the setlist from night to night, yet Waits isn’t one to take requests from the crowd, despite persistent (and vociferous) calls to do so. “We’ll play all your favorites,” he quipped like a vaudevillian master of ceremonies in a futile attempt to calm the maelstrom.

In fact, part of the kick of seeing Waits in concert is experiencing his humor and wit first-hand. He halted “Chocolate Jesus” after the first verse, saying, “If you’re going to clap, please elect an official.” Before continuing the song (which he sang through a red megaphone), he remarked in mock admonishment, “Keep the tempo.”

The inclusion of Omar Torrez on guitars and Vincent Henry on woodwinds instilled the music with jazz and Latin inflections, giving songs like “Hoist That Rag” (with Waits shaking a pair of maracas), “16 Shells From A Thirty-Ought Six,” and “Get Behind The Mule” a loose, buoyant feel. And on a particularly swinging version of “Black Market Baby,” if you let your focus drift a bit, you almost expected to hear, “Hello, Dolly. Dis is Louis, Dolly.”

Accompanied by Seth Ford Young on upright bass, Waits sat at his baby grand for a triad of ‘70s gems, beginning with the back-to-back tour debuts of “On The Nickel” and “I Can’t Wait To Get Off Work.” Much to the crowd’s amusement, he also took the opportunity to dig into his voluminous supply of indiscriminate facts. “There are more insects in one square mile of earth than there are people on the entire earth,” he said. “Imagine if they could vote.”

He also traded barbs with good-natured hecklers. “I want to have your baby!” one man shouted from the back of the hall. “Nowadays that’s possible!” Waits retorted in a snap. “Talk to my manager… But my sperm, it’s expensive. I’m like a fuckin’ racehorse.” Returning to playing “actual songs,” he then capped off the segment with a strikingly earnest rendition of “Invitation To The Blues.”

For a man notorious for his gruff voice and peculiar, scrapyard-sound arrangements, Waits delivered an assortment of ballads that ultimately proved among the finest performances of the night. On songs like “Anywhere I Lay My Head,” “Cold Cold Ground” (featuring keyboardist Patrick Warren on accordion), and “House Where Nobody Lives” (with his youngest son, Sullivan, on “assistant clarinet”), Waits exhibited cinematic breadth and magnificence. In doing so, he captivated the audience not just with the brilliant idiosyncrasies of his music, but also with the craft with which he invests it.