By the summer of 1958, Pete had left school when his step-dad died and began working in a show band for Disneyland DateNites, playing bass. After finishing a round of golf one day with Skiles, Bill offered to drive Pete out to Disneyland to pick up some of Pete's paperwork in the entertainment office. Bill started clowning around for the secretaries and Tommy Walker suddenly peered out at them from his office door. Even after two years he still remembered the name - "Is that Skiles and Henderson?" he asked. Then he went on to describe a new stage called the Plaza Gardens that might be right for the duo. They re-auditioned there the next day, were hired and began their long career on June 13, 1958.
Their 20-minute show wasn't all music, although the musical tire pump and the tin can xylophone and the tuned skillets and musical saw and washtub bass were a large part of the act. They starting working new material into their show lampooning the various "lands" comprising the park. Frontierland, Adventureland and Tomorrowland all were grist for the Skiles and Henderson mill. Sound effects became important to their style and remain so today.
At the end of their first summer at the park their workload was reduced to weekends only. They were asked to participate in a new program called Tour Guides but that only lasted a short time for them. By the summer of 1959, they were leading their own DateNite band in Frontierland and still had their day job in the park. But it was time to move on to the real world. In 1972, the duo started touring with The Carpenters, doing the first half of the singers' concerts and Pete singing in the Carpenter's "Oldies Medley" at the end of each concert. At this time, they made a brief return to Disneyland as the hosts of the Mouse Factory episode "Music", where they incorporated pie-in-the-face gags into a few of their comic acts. They also voiced the monkeys in The Jungle Book.