Bryant's only win on the PGA Tour came at the age of forty at the 1995 Walt Disney World/Oldsmobile Classic, which took 20 years and 475 starts to achieve, one of the longest waits for a PGA Tour win. After reaching the age of 50, Bryant began play on the Champions Tour, where he won for the first time at the 2006 Toshiba Classic and followed up later the same year by winning the Regions Charity Classic. He lost to Jay Haas in a playoff for the 2006 Senior PGA Championship. His best year in professional golf was 2007, when he finished third on the Champions Tour money list and fourth in the Charles Schwab Cup race; that year was highlighted by his victory at the U.S. Senior Open.[3][4]
Bryant's younger brother Bart also won on the PGA Tour.[3][4]