Ignoring the fact that it was six degrees outside, throngs of country fans stood outside the Orpheum Theatre Saturday night, forming an unsystematically muddled line that spanned the entire block from State down to the corner of Johnson Street. Cleary, Kip Moore was in town.

Rising country star Chris Cavanaugh began the night, playing lively tracks that drew the enthusiastic crowd’s attention. Despite his newcomer status in the country music scene, Cavanaugh appeared a natural-born musician as he freely jammed on his guitar and busted out canorous lyrics. Cavanaugh’s suave performance stems from his passion for music that began when he was 12 years old growing up in his hometown of Springfield, Miss. He had been entranced by the sounds of traditional country music heroes George Strait and Garth Brooks from an early age, and he used them as inspiration to pursue what he loved — singing and songwriting. What makes this young star all the more popular is the way that the lyrics to his music are largely influenced by his ordinary roots, and therefore strike a connection with the easygoing, average Joes that typically constitute the country music fan base. Ergo, Chris Cavanaugh was a hit.

Following Cavanaugh’s performance, the next opening act hit the stage. Drake White and The Big Fire set off on what would be an hour’s worth of a fresh variation of country heavy on the rock influences. White dances the border between country and rock, reminiscent of the cherished outlaw countries — like Waylon Jennings and Johnny Cash — who made headway in late 1960s and 1970s. At times, White’s raw, haggard vocals developed into the sounds you would expect from Southern alt rock band Kings of Leon and the indie blues rock gods The Black Keys. This Nashville startup’s distinctive expression is racking up the accolades, and as of late the group has been on tour with an increasing number of esteemed musicians, including Eric Church and Luke Bryan. White is undoubtedly inching his way up to mainstream stardom.

The well-received opening performances ended as Kip Moore made his entrance around 9:30 p.m., dressed in his signature backwards caps and sleeveless T-shirt. Moore dressed according to the venue, bearing a red cutoff with the word “Wisconsin” on it. The Madison crowd greatly appreciated this. The artist riled the audience with each song and earned the affection of the packed theatre with the drunken anecdotes he rattled off between each track. At one point Moore engaged in a long-winded, hashtag-filled speech about selfies and the wonders of contemporary social media, upon which he apologized saying, “I’m just kinda rambling now … I’ve had a lot of Jack Daniels tonight,” a statement that instantly elicited the applause from the similarly intoxicated spectators.

Love was a repeated theme of the night. At one point, Moore accounted the various stages of a breakup. As he said, “first you’re sad, then you’re pissed off.” He described one of his breakups from when he was 21 years old. He went off alone in a field in his birthplace in Southern Alabama. There he smoked Marlboro Reds and drank Budweisers to the point where he was no longer sad or pissed. And this theme made a glorious segue into the most memorable point of the night when an old friend of Moore proposed to his long-time girlfriend right in front of the stage with Moore serenading the couple, singing “Young Love” and “Hey Pretty Girl,” before closing out with his spirited song “Somethin’ ‘Bout a Truck.” Moore and the band made it back for an encore and performed “Faith When I Fall” and Tom Petty’s “Free Fallin’.” These tunes warmed the room with a measure of nostalgia and made for an affable end to an impressive string of performances.