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Jennings had all the work he could handle, and was earning $500 a week from performing alone before the end of WWII. "There was so much work I hired someone to drive and I slept in the car!" he said. "I did my two shows at night and came back to work during the day at the Elliott Company. As long as I got my job done they didn't care what time of day I did it."

He had the resources to drive Cadillacs, buy an airplane and own his dream house. In 1948 he and Ruth bought a big house at 400 Hampton Ave. in Pittsburgh that had two rooms and a bath specifically set aside for jugglers working in town. The list of temporary tenants at what became known simply as "400" was a "Who's Who" of entertainers of the era.

In the years just before he war he began performing as The Bum Juggler, a lackadaisical, scruffy clown who turned out to be a pretty talented juggler. It grew and evolved some through its end in 1955, eventually adding oversized clubs and black lights. The act was designed to work in the "one" spot on a stage, the area in front of the main curtain. The finale always required the whole stage, and while that was being set up behind the curtain Jennings performed 12 minutes in front of the curtain. All major theatres such as his favorite, the Hartman in Columbus, Ohio, kept a supply of dozens of sets that the artistes could use. For Jennings' act, the theatre lowered some tree flats and pulled in a bench to create a park setting.

While Art was entertaining out front, stage hands installed a huge double flight of stairs behind the curtain for the finale, which featured all 24 performers in the show. "They installed a whole new set right behind me in just those 12 minutes and I never heard a sound, even though I did a silent act," said Jennings.

The War changed many things, including the world of entertainment. Even as the good times of the pre-war and war years rolled on, changes in the business began to threaten prosperity for the practicing juggler. Jennings identifies the one-two punch that knocked the old ways out cold as unionization and television.

He speaks somewhat bitterly of unions because he believes they helped kill show business even before television did. It began when the musicians union instituted a requirement that any house hiring three acts had to have five musicians. Prior to that, the majority of variety houses just employed a piano and drummer during the week, though they had a full band for weekend shows. When proprietors were required to hire five musicians any time they had three acts, they cut out acts to avoid the extra expense for musicians.

Shortly after the end of World War II, the American Guild of Variety Artists (AGVA), Screen Artists Guild (SAG) and American Federation of Radio and TV Artists (AFTRA) began setting minimum wages for performers. Jennings explained, "Prior to that, beginning dancers would make $3-$5 a show, and as a top act at a banquet I could make $150-$250. But the AGVA said no act could work for under $25, and you had to have a certain number of acts of your show. To meet the client's budgets, the agents then had to cut the pay of the top acts to accommodate the minimum wage for other performers."

Another change was new laws that banned slot machines from clubs, which reduced the income for club owners and made them disinclined to hire entertainers. In addition, Harry Lind was getting old and no one else was making clubs. It looked like even those who wanted to juggle might not be able to find any props. As the old rules changed, theatres closed and jobs dried up, Jennings began to fear that the art of juggling might be lost completely.