Wynn had his first #1 song "Have You Forgotten" with Darryl Worley in 2003. The song was nominated for SONG OF THE YEAR by the CMA. In 2008, Waitin' on a Woman, which Wynn co-wrote with Don Sampson was nominated by the CMA for SONG OF THE YEAR. His most recent #1, I'm a Little More Country recorded by Easton Corbin, was also nominated by the ACM for SONG OF THE YEAR.
Wynn’s songs have been cut by a range of great artists, including Easton Corbin, Garth Brooks, Lee Ann Womack, Brad Paisley, Darryl Worley, Kellie Pickler, Montgomery Gentry, Jason Sellers, Gary Allan, Trace Adkins, Clint Daniels, Kevin Denney, Tracy Byrd, The Kinleys, Chris LeDoux, Danni Leigh, Mark Chesnutt and Sammy Kershaw.