Crayton attended DeSoto High School, where he played as a wide receiver, quarterback, running back and return specialist.
He accepted a scholarship from Northwestern Oklahoma State University, where he was a wide receiver in his first three seasons, before switching to quarterback as a senior.
While leading the Rangers to the 2003 NAIA National Championship game his senior year, Crayton passed for 1,837 yards and a school-record 19 touchdowns.
He became the first player in NAIA history to score a touchdown passing, receiving, rushing and on kickoff and punt returns in a single season.
However, he sustained a broken ankle on October 16 against the New York Giants, and was unable to return to full form until December 24.
The 2006 season brought Crayton back to renewed prominence, especially when the Cowboys switched quarterbacks mid-season to Tony Romo.
In the Wildcard playoff game against the Seattle Seahawks, Crayton had a diving touchdown reception in a losing effort.
In the divisional round, where Dallas lost to the eventual Super Bowl XLII Champions, New York Giants, he dropped a pass that would have resulted in a critical first down if not a touchdown.
[5] In 2010, he dislocated his left wrist in the second quarter of the tenth game of the season against the Denver Broncos, after making 3 receptions for 105 yards and one touchdown.