Denny left the band for college in Omaha in September of 1964. He continued to play bass with an Omaha band, but eventually concentrated on his studies and sold his bass and amp.

In Omaha, Denny met Dean Short, through a referral from Stew Scott, who had appeared in 1962 at the Pocahontas County Fair. In August of 1962, Scott introduced Denny to Ken Spencer, noted Minneapolis vaudeville ventriloquist and ventriloquist figure maker. When they met at the Spencer home, Ken had a dummy he had carved for another ventriloquist, who couldn't come up with the $115 price tag when the figure was completed and ready for delivery. Denny bought the dummy on the spot. Back at the Minneapolis hotel, Stew trimmed a woman's wig to give Benny his Beatle haircut, which Benny still wears today.

Dean Short, a puppeteer, operated a music studio out of his home in Omaha, where he taught 60 students a week. As a booking agent, Dean managed acts who performed for school show tours. Denny visited Dean's studio with Benny several times during the fall of 1964 for some technique pointers. Dean taught Denny a few standard ventriloquist jokes, a couple songs and comical bits.

Serving as Denny and Benny's first booking agent, Dean booked the act with other local acts in shows around the Omaha area. Between 1964 and 1971, when Denny graduated from law school, Denny and Benny performed throughout Nebraska, Iowa, South Dakota, Kansas, Missouri and Minnesota, working for several booking agents in the Omaha area, including Dean Short, Sammy Stevens Trio, Subby Ansaldo, Jimmy Clark and Don Romeo Entertainment Agency. In addition, they worked shows booked by the Ralph Zarnoff, Des Moines band leader, and Fred Fenchel Entertainment.

Throughout the 1960's, Denny performed each year in competition in the Iowa State Fair Talent Contest, winning the event over 1,000 other acts in 1966. During those years, Bill Riley, announcer and manager of the Iowa State Fair Talent Contest, booked regularly Denny and Benny to perform as filler during the judging of talent contests around the state of Iowa that he wasn't competing in. During holiday times and whenever needed, Zarnoff and Riley booked Denny and Benny in Des Moines for corporate parties and shows and local events.

Usually performing as an opening or filler act, Denny and Benny appeared with such notables as Trisha Nixon and the nationally known clown, Emmet Kelly, Jr.

From 1964 through 1971, Don Romeo and Fred Fenchel kept Denny and Benny busy, traveling with Grand Ole Opry stars, such as Mel Tillis, Loretta Lynn, The Cates Sisters, The Cantrells and Lynn Anderson. His summers included tours with Lawrence Welk Show regulars, Larry Hooper, The Lennen Sisters, Joe Feeney and Joanne Castle. They appeared at bigger fairs and rodeo events with TV cowboys, Rex Allen, Poncho Gonzales, Pat Buttram, also famous for the TV show, Green Acres,with Homer the Pig and a tour with Rudd Weatherwax and America's most famous dog, Lassie.

While school was in session during those years, Denny and Benny averaged 30 Cub Scout Blue & Gold banquets per year, worked numerous corporate parties and trade shows, did a series of TV commercials for Omaha's Brodkey Jewelers, often chartered an airplane in order to entertain audiences in Western Nebraska, Northern Iowa, Kansas and Omaha during the Christmas season. They even appeared with the Omaha Symphony at a Pella College Prom in 1969.

While in law school, Denny played folk guitar as Denny McDonald, on a radio show he co-hosted with Jim Higgins, whose name on the show was Allen Blake, also the show's name. The show ran in a small Omaha market for about a year. In 1970, Denny again took up the bass guitar to form The Joint Concern, working supper clubs and banquet events with pianist, Tony Dalton. Benny always performed as well.

While practicing law in Dubuque, Iowa, Denny regularly appeared with Benny at conventions, corporate meetings and banquets, Christmas parties, fairs, grand openings and private parties. These days, they are popular with Chamber of Commerce organizations, Pork Producers, Cattlemen's Associations, Dairy Producers and every kind of cooperative and corporate meeting imaginable . They have appeared in more than a dozen states, from Hollywood to Boston, and in two countries in Europe.

Playing his Little Lady harmonica, Benny has become an accomplished musician, but his application to join the musicians union has been rejected numerous times. Working with Benny hasn't helped Denny's reputation as a lawyer, even though he honestly admits being the only attorney in America who admits talking out of both sides of his mouth. More than one judge has accused Denny of making witnesses talk in court, and one judge has requested him to do so.