Checker's releases cover a wide range of genres including blues (Little Walter, Sonny Boy Williamson II), rhythm and blues (Sax Mallard, Jimmy McCracklin), doo-wop (The Flamingos, The Moonglows), gospel (Aretha Franklin, Five Blind Boys of Mississippi), rock and roll (Bo Diddley, Dale Hawkins), and soul (Gene Chandler).

[3] The label's most popular artist, in the label's early years, was Little Walter, who had ten songs released by Checker that made the Top Ten of Billboard magazine's Top Rhythm & Blues Records charts.

[5] On March 2, 1955, the Chess brothers recorded their first rock and roll artist, Bo Diddley.

From this session came Bo's self-titled debut single on Checker,[7] which topped the R&B charts[5] and was inducted into the Grammy Hall of Fame in 1998.

[6] In 1957, Checker cracked into the rockabilly market with Dale Hawkins, who had a crossover hit with "Susie Q", although he could not repeat the single's success.