Clifford Fredrick John Ostermeyer

“Cliff Ayres”

September 21,1923 – February 16, 2021

Clifford comes from a community of farmers in northeast Indiana. In the fall of 1923 while traveling through Preble, Indiana in a horse-drawn wagon, Edwin and Janetta Ostermeyer made an unexpected stop at a farmhouse on the side of the road so “Nettie” could give a difficult breach birth to their first child, a son named Clifford.

Cliff and his brother Walter and sister Mary Ann were raised during the depression in Fort Wayne where their parents ran a men’s boarding house in their 3-story home on Creighton Avenue. It was popular with German immigrants because of the name Ostermeyer and because his parents spoke German. In the summer Cliff would live and work on his aunt’s and uncle’s farms, mainly Walter Ellet’s farm.

For fun, Cliff would sometimes get to visit the Fort Wayne fire station No. 3, which is now a museum, where his dad was a city firefighter. The neighborhood kids would play tag on the hook and ladder truck, which was the largest truck in the city at that time.

After graduating from South Side High School, he joined the Army during World War II where he served from 1943 to1946. Although issued a helmet, he preferred to show off his pompadour hairstyle. As an Entertainment Specialist he sang in USO shows with fellow service men, Johnnie Ray and Anthony Bennedetto, later known as Tony Bennett. He stayed an extra year in Europe to entertain the troops who were waiting to get back to the states after the war.

For several years after the war Cliff lived in New York City and pursued a career in entertainment using the stage name Cliff Ayers. He was thrilled to sing onstage with big bands of the day including Sammy Kaye and Jimmy Dorsey at the Rainbow Room and the Waldorf Astoria hotel. Prior to forming his first independent label, Emerald Records, he recorded for Decca, Columbia, and Roulette.

Transitioning back to Fort Wayne in the early 1950s to start a family with his wife Jeanette, he continued to sing in clubs and record. His entrepreneurial spirit was evident throughout the 1960s as he owned or managed several small businesses including a tv repair shop, nightclubs, rental properties, and an entertainment newspaper. He also created and starred in a television show called, “Breakfast in Fort Wayne”, which was one of the first television shows that originated in Fort Wayne. In 1968 he was nominated to run for political office on the Democratic ticket for state representative.

In 1973 he moved to Nashville, Tennessee, and continued to sing and record. He changed the name of his newspaper to the Music City Entertainer, and started a record label where he recorded and produced a wide range of artists. While living in Nashville, he would often commute to Miami for business and occasional singing gigs. In 2003 he became involved with the creation of the Big Band Hall of Fame in West Palm Beach, Florida and was also a member.

Cliff was always happy when he had a boat parked in the driveway ready to go. Some of his favorite pastimes were fishing for bluegill, attending airshows at Baer Field and elsewhere, the Auburn Cord Duesenberg festival and auction, going to the dog races in Florida, watching classic films, going to Hall’s restaurant, seeing relatives at family reunions, and an impromptu performance for anyone who asked.

Semi-retired, by 2005 Cliff settled in Fort Lauderdale with his companion Ursel Blanco. In 2017

he moved to Indianapolis to live with his daughter, Tessa before they both relocated back to Fort

Wayne in 2019.

Clifford died peacefully at home. He was preceded in death by his parents Edwin and Janetta (Elett) Ostermeyer, sister Mary Ann (Wayne) Keefer, son Christopher, and daughter Celeste. He leaves behind his sons Clark Ostermeyer and Curtis (Alice) Ostermeyer, his daughters Tina Ostermeyer and Tessa Ward, all of Fort Wayne, four grandchildren, one great grandson, his brother Walter Ostermeyer of Fort Wayne and several nieces and nephews.

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