He started his broadcast career in 1927 as a staff announcer for WOR in Newark, New Jersey. He was the announcer for DuMont Television Network's talent show Doorway to Fame in 1947, but he left DuMont for WPIX on May 15, 1948 to be a news announcer and weatherman.
On January 17, 1955, he appeared as "Officer Joe" and hosted The Clubhouse Gang, which featured the Little Rascals and the theme song "The Whistler and his Dog". WPIX lost the rights to The Little Rascals, and in September 1958, he switched to hosting The Three Stooges Funhouse, a showcase of The Three Stooges shorts which aired on WPIX weekdays until May 7, 1970, mostly weekdays at 5:30 pm. At one time, he was host of WPIX's The Dick Tracy Show as "Police Chief Joe".
Bolton also had cameos in two Three Stooges films: Stop! Look! and Laugh (1960), as a customer in a cafe; and in The Outlaws Is Coming (1965), the last feature film by The Three Stooges, which featured him and eight other local children television show hosts, all cast as villains.