Telling the story behind many of the songs off his latest release, The Bluegrass Album, Jackson also reflected on his many visits to New York City. "I've played the Beacon Theater, Radio City, Madison Square Garden, CBGBs," he said. "It's amazing for an ol' boy from Georgia who never traveled anywhere 'til I was 25."

As he introduced his eight-piece backing band, which included mandolin, fiddle, upright bass, banjo, acoustic guitar, Dobro, and backing singers, Jackson let the audience know they were in for a treat. "I hope you all like good music and good picking."

While his die-hard fans were present, Jackson didn't stray from the bluegrass theme of the night, despite their continuous screams for past country hits of his such as "It's Five O'Clock Somewhere," "Remember When" and "Someday." He did, however, play the poignant "Where Were You (When the World Stopped Turning)," a 9/11 tribute, which earned him a rousing standing ovation.

The night also included an ode to George Jones. In prefacing "Blue Side of Heaven," Jackson talked of how he got word that the country legend was sick and near his last day. Visiting him in the hospital, while it was evident Jones was fading fast, his personality was still big as life, as was his singing.

"I've always been drawn to the sad songs. They've always come easier," Jackson explained. "Sad songs just fall out. George . . . in the hospital his body was giving out, but he still sang like George. Laying there, he knew he was dying." (Jones passed away this past April 26.)

Jackson sent the song "Blue Side of Heaven" to George's wife, Nancy Jones, after his passing. Accompanied by soaring fiddle, Dobro and slide guitar, Jackson's emotional vocals filled the performance with his own personal sadness and brought the song to life.

Lee Ann Womack lightened the mood next during a surprise appearance, with Jackson singing her praises before she walked onstage for a duet. Calling her "one of my favorite country singers," Jackson added that he's been a fan "since she sang that first note on that first album." The two sang a striking cover of Don Williams' "Lord, I Hope This Day Is Good," which showcased Womack's memorable vocals.

Throughout his two-hour set, Jackson peppered his performance with stories of his family and where he grew up, as well as select cover songs. These included John Anderson's "Wild and Blue," a song he says he's always loved, and set closer "Blue Moon of Kentucky" by bluegrass founder Bill Monroe, both of which appear on his album.

Jackson also brought out nephew Adam Wright, who wrote "Ain't Got Trouble Now" and coproduced The Bluegrass Album, to sing lead vocals as he sat on his stool and let him take the spotlight. This is in fact something he did throughout the evening: Every time a band member had a solo, Jackson would step back and point to the soloist, urging the audience to take notice.