The son of a Louisiana sharecropper, legendary bluesman and Rock & Roll Hall of Fame inductee George “Buddy” Guy first arrived in Chicago in 1957, penniless and hungry, but he impressed Muddy Waters and started playing in his band. In the 1970s, Buddy kept his ’58 Stratocaster behind the bar at his own club, the Checkerboard Lounge, to challenge any ambitious patrons. Many lean years later, Guy opened his current club in 1989 in a 1910 South Loop building owned by Columbia College, just prior to his breakout 24 Nights tour with Eric Clapton. Legends today features top-notch blues, though Buddy Guy himself only plays in January as part of his annual, month-long tenure. Like Guy’s former club, Legends has kept true to its name by hosting the Rolling Stones, Eric Clapton and Koko Taylor. The crowd consists mainly of tourists, suburbanites and blues aficionados. In January 2007, Buddy Guy announced his club would close due to Columbia College’s plan to build a student center but they relented. As with the Checkerboard before, the club is part of a promise made to the late Muddy Waters to keep the blues alive on Chicago’s South Side. Legends is also a must-visit during the annual Chicago Blues Festival every June… you just might find Buddy Guy himself sitting at the end of the bar, sipping the beloved cognac that he calls “Connie.” For more information, check out the Buddy Guy’s Legends website.