Like executives at many companies, Robert J. Coury, executive chairman of generic drug maker Mylan Inc., is allowed personal use of his employer's corporate jets.

Unlike most executives, Mr. Coury also has a side business: a record label that promotes the fledgling music career of his son, Tino Coury, a young pop singer with a Top 40 hit in 2010 and a new album released online last month.

In a mingling of these two parts of the Mylan chief's life, federal flight records show that one of Mylan's two jets has frequently flown to the same cities in which the younger Mr. Coury was playing a concert. On some occasions, the jet—a Bombardier Global Express the size of a regional airliner—flew directly from one of Tino Coury's concert locations to the next.

On July 3, 2010, for example, Tino Coury performed a late-night gig at a Cincinnati nightclub. At 3:18 a.m., the Mylan jet left Cincinnati for West Palm Beach, Fla., arriving there around 5 a.m. Later that day, Tino Coury performed at a July 4th concert in West Palm Beach.

The following week, Tino Coury performed near Hartford, Conn. Shortly afterward, the Mylan jet traveled from Hartford to Las Vegas, where he had his next performance. Based on the aircraft's estimated hourly operating cost, the tab for the one-way flight was about $22,000.