The Sinatra tributes are becoming an annual tradition for Eldredge, who grew up singing pop standards popularized by the likes of Ol’ Blue Eyes. In the video above, he gestures with a half-full highball glass while ripping into “Come Rain or Come Shine,” the mid-Forties Broadway tune that made a memorable appearance on Sinatra & Strings in 1962. A small horn section contributes blasts of brass behind him, while bartenders at the Skull’s Rainbow Room — an alleyway bar that opened its doors in 1948, just two years after “Come Rain or Come Shine” was first published — serve up the sort of fussed-over drinks the Rat Pack might’ve once ordered.
Midway through the show that night, Eldredge announced an interest in turning the yearly event into a holiday-time charity performance. Although official details have yet to be announced, the singer’s tour schedule currently ends with a November 19th performance at the Barclays Center in Brooklyn, leaving him just enough time to head back to Nashville and rehearse with a big band before the annual Sinatra gig.