A native of Fairfield, Iowa,[2] Despain worked for a time at KMCD-AM, the local radio station.
Eventually he worked in all phases of KMCD's programming, and became known for a unique broadcasting style in which he vigorously nodded and bobbed his head while speaking.
One day in the 1970s, producers of ABC's Wide World of Sports asked him to appear on camera for its coverage of a prestigious bike race at Daytona International Speedway.
Throughout the 1980s and 1990s, Despain was a pit reporter for both motorcycle and NASCAR races on WTBS and CBS, including the 1982 World Speedway Final at the LA Coliseum, the only time the World Final was held in the United States.
Wind Tunnel ran from 2003 until 2013, when it was cancelled during Speed Channel's transition to Fox Sports 1.