Kenny Chesney Plays Surprise Show at Nashville Honky-Tonk

The Wailers, Kid Rock Join Him Onstage at Tootsie's Orchid Lounge

“If I can’t sing Wednesday night, this is why.”

Reigning CMA entertainer of the year Kenny Chesney lived up to his title Monday night (Nov. 10) as he played to a jam-packed crowd at Tootsie’s Orchid Lounge in Nashville. Only two days prior to Wednesday’s (Nov. 12) CMA Awards, this year’s seven-time CMA nominee played well into the wee hours of early Tuesday morning.

Beginning just before 10 p.m., Chesney made his way through the tightly-packed crowd and took the stage in his Detroit Pistons ball cap, gray T-shirt and jeans.

“Thank you all for coming,” he said. “We didn’t know we were doing this till 3 this afternoon.”

Those fortunate enough to receive VIP passes to the last-minute show were allowed to enter through the back-alley entrance closest to the stage Chesney was playing. All others were directed to the front of the bar located on Broadway where they squeezed, pushed and/or forced their way to join the others. Finding a spot to stand wasn’t easy, but the minuscule space left near the back door provided some breathing room.

Chesney began with his No. 1 song, “Beer in Mexico,” and followed it with fan favorites “Summertime,” “Young,” “Big Star” and “Never Wanted Nothing More.”

During his set, security guards worked hard to keep the peace between the increasing mass of overly-excited people, even throwing a man out at one point for causing a ruckus. But that wasn’t Chesney’s fault, and the music didn’t miss a beat.

“Several years ago,” Chesney said. “I recorded a song that’s become an anthem for us on the road.” He then introduced singer-songwriter Mac McAnally, who’s nominated for this year’s CMA musician of the year, to join him onstage for “Back Where I Come From,” a song McAnally took to country radio in the early ’90s. The two then performed “Down the Road,” the current single and duet from Chesney’s Lucky Old Sun album.

Adding to the excitement, the Wailers, best known for backing the late reggae icon Bob Marley, joined Chesney for “Everybody Wants to Go to Heaven,” a song featured on Chesney’s latest album. They followed with renditions of several favorites they recorded with Marley, including “No Woman, No Cry,” “I Shot the Sheriff” and “Stir It Up.”

As if Chesney and the Wailers performing together wasn’t surprise enough, Chesney introduced his “friend from Detroit” — Kid Rock — to the mix where they all sang an astounding rendition of “One Love/People Get Ready,” another classic from Marley and the Wailers. Seeming to enjoy his collaboration with Chesney as much as he enjoyed the crowd, Kid Rock lit a cigar and continued to sing along to Lynyrd Skynyrd’s “Gimme Three Steps” and the Eagles’ “Take It Easy.” Out of the blue, the two burst into a Kid Rock medley with Chesney shouting, “Rock that b**** up and down the coast,” lyrics from Kid Rock’s Top 10 rock hit, “Cowboy.”

The night and early morning were successfully filled with a diverse mixture of familiar songs. Fans and musicians alike shared the night singing an array of tunes ranging from Alabama’s “Dixieland Delight” to U2’s “With or Without You” and many, many others.

A tireless Chesney successfully turned a routine Monday night at Tootsie’s into an unforgettable evening as he ended his three-hour jam session.

But for those unable to attend, not to worry. Chesney and the Wailers will return to the stage Wednesday night at Nashville’s Sommet Center as they perform “Everybody Wants to Go to Heaven” and the Wailers’ “Three Little Birds.” The show will be broadcast live on ABC.

Writer/producer/voice over talent for