Hit-Boy Ft. Kid Cudi – Old School Caddy 0 By Brandon Butch on July 30, 2012 Music After teasing us with it a while back, Hit-Boy finally releases his new single Old School Caddy, featuring Kid Cudi. This one sounds much better than his last effort, Jay-Z Interview. Share. Twitter Facebook Google+ Pinterest LinkedIn Tumblr Email Want More? Since it's almost impossible to keep up with everything in hip-hop, we drop new emails weekly to ensure you're always in the loop with news, release dates, new music and much more. Make sure to sign up today! 100% Privacy. We don't spam.