Bloodshot Records was born in a late-night Chicago bar, with some simple ideas scrawled out on a cocktail napkin. And ever since their very first album release in 1994, 'For A Life of Sin: A Compilation of Insurgent Chicago Country,' the esteemed label has been a bright and steady beacon in a shifting musical landscape. That first compilation included local Midwestern greatness like The Bottle Rockets, Robbie Fulks, The Handsome Family, Freakwater, and of course Jon Langford (The Mekons), whose commitment in bands like The Waco Brothers and Pine Valley Cosmonauts – not to mention his striking artistic work – is closely connected with the history of Bloodshot, spawning the term “insurgent country” for which the label is renowned for. Predating the Americana wave to come later in the '90s, Bloodshot soon spread out across the nation to become nearly synonymous with rootsy rock ‘n’ roll, country punk, and shining singer-songwriters seemingly unfit to belong anywhere else. Initially dropping releases from the likes of Old 97’s, Neko Case, Waco Brothers, and Ryan Adams ('Heartbreaker' being their biggest seller of all time) laid the foundation for which they’ve carefully built and gradually developed over the years. Newer artists includes Justin Townes Earle, Lydia Loveless, Luke Winslow-King, and Maggie Björklund, as well as legends like Graham Parker, Andre Williams, The Sadies, and Alejandro Escovedo. And even though it has always stayed true to their roots, Bloodshot has never stagnated in one particular shape, save the one for releasing quality music. Going through their massive catalog and choosing highlights is an exciting task of monumental proportions, and also serves as a reminder on how vital, diverse, and fun their output has been. This playlist is by no means a complete collection of their highlights, but serves as a humble introduction hopefully leaving you eager to hear more.