As the weather warms up, many Chicagoans’ minds turn to baseball. Despite injuries, contract negotiations, and other issues, Sox and Cubs fans always have hope this time of year as a new season stretches out before them.

Harry Caray, longtime Sox and Cubs broadcaster, often spread this early season cheer. Whether handing out beer, taking a shower in the stands, trying to pronounce players’ names backwards, or broadcasting from the bleachers, he made watching and listening fun despite the score or the season’s prospects.

While he did call other professional and some college sports, Caray rose to fame as the St. Louis Cardinals’ broadcaster from 1945 to 1969. He arrived on Chicago’s South Side to announce Sox games in 1971. By 1976, famous Sox owner, Bill Veeck, had Caray singing “Take Me Out to the Ball Game” during the seventh inning stretch at Comiskey Park.

With a change in ownership, Caray left the Sox and replaced Chicago baseball legend Jack Brickhouse starting with the Cubs’ 1982 season. Caray’s stardom grew on the North Side. With the Cubbies’ games on WGN-TV’s Superstation, fans across the country heard his renditions of “Take Me Out to the Ball Game” from Wrigley Field. Over the years, he hosted numerous celebrities and notable figures in the Cubs’ broadcast booth, including President Ronald Reagan and then First Lady Hillary Rodham Clinton. After more than five decades of broadcasting, he died in 1998.

See more images from Harry Caray’s storied career, which includes opening Harry Caray’s Bar and Restaurant and launching his Holy Cow Sodas soft drink line.