The borders around whatever constitutes country music were awfully loosey-goosey long before hick-hop was a thing. Everyone from the original hillbilly and rockabilly cats of the ‘50s through the Californian hippies of the ‘60s to the outlaws of the ‘70s all stepped back and forth along the genre’s boundaries in their own music. In the ‘90s and beyond, country artists began to reach across the proverbial aisle to their brethren and sistren in the rock and hip-hop worlds. Of course, the crossovers flourished in the other direction as well, with former rock-world types like Kid Rock and Hootie & The Blowfish’s Darius Rucker finding warm homes on the state-fair circuit. Those traditional distinctions have never seemed as blurry as they do today, in an age when even the most seemingly unlikely cross-genre matchups—whether it’s Willie Nelson and Snoop Dogg or Carrie Underwood and Ludacris—hardly raise an eyebrow. The success of Uncle Kracker is a big reason why country got to be such a broad church (and sometimes a weird and wild one, too).Uncle Kracker’s buddy and former employer Kid Rock may have busted the field wide open with his redneck-MC routine on 1998’s “Cowboy,” but Uncle Kracker’s own pair of smashes with “Follow Me” and “Drift Away” in the early 2000s may have been even more influential. Here was a sound that somehow spiked a down-home and eminently country brand of mellow with the brasher edge of hip-hop. Around the same time, a scrappy Timbaland protégé by the name of Bubba Sparxxx was scoring hits with rawer variations on this new hybrid.You might expect that artists in the country world would not take too kindly to these incursions into their traditional terrain. But if anything, it was a cue for them to get bolder, too. The swagger brandished by superstar duo Big & Rich suggested a greater kinship to Jay-Z than with any old-timers at the Grand Ole Opry. Hell, Big & Rich even have their own Wu-Tang-like posse in MuzikMafia, a loose collective that has dominated country music for much of the century thanks to the duo’s own hits and those of friends and sometime collaborators like Gretchen Wilson and hick-hop icon Cowboy Troy. Given that overall spike in badass attitude, the rise of bro-country stars like Jason Aldean and a new wave of proudly redneck MCs like Colt Ford and Upchurch was inevitable.So where this kind of hybridization still seemed like a novelty in 2004 when Nelly and Tim McGraw delivered “Over and Over”—still the quintessential country-rap slow-jam—it’s now a testament to the fact that American popular music might as well be one giant purple state. And Uncle Kracker helped make it all possible, which is why he belongs in this playlist of essential songs and artists that forced open the rusty gates of country music’s corral.