Frye graduated from Willard High School in Willard, Ohio, and was a football standout at quarterback under coach Chris Hawkins. He broke 17 of the school's all-time football records. In his senior season, Frye led the Crimson Flashes to a 10-2 record, earning the Northwest District Player of the Year award and First-Team All-Ohio Division III team honors. Frye excelled in basketball; during his senior season he earned First-Team All-Northwest District and Honorable Mention All-Ohio Honors and helped lead the Crimson Flashes to a 22-3 record, a Northern Ohio League Championship and a Sweet 16 berth.
Frye broke 54 football records during his college career at the University of Akron. After red-shirting in freshman year, Frye was named starting quarterback in just the second game of his freshman season. Frye won the MVP award at the 2005 Senior Bowl in Mobile, Alabama.
Source:Numbers in Bold are Akron school records
Frye was selected in the third round (67th overall) of the 2005 NFL Draft by the Browns. His first NFL start came against the Jacksonville Jaguars in week 13. He passed for 226 yards with two touchdowns, both to fellow rookie Braylon Edwards, and set a Browns rookie record for a single game with a 136.7 passer rating. Frye started the final five games of the 2005 season for the Browns, compiling a record of 2-3.
Frye was named starting quarterback for the 2006 NFL season.
After a battle in the preseason with Derek Anderson and rookie Brady Quinn, Frye won the starting quarterback job for the 2007 season. In the first game against the Pittsburgh Steelers, Frye struggled during the first few minutes. Anderson replaced him for the remainder of the game. Anderson remained the starter for the rest of the year and made the Pro Bowl.
On September 11, Frye was traded to the Seattle Seahawks for a sixth-round draft pick. He was the Seahawks' third-string quarterback behind Matt Hasselbeck and Seneca Wallace. Frye made his first start of the 2008 season against the Green Bay Packers.
An unrestricted free agent following the 2008 season, Frye signed with the Oakland Raiders on June 8, 2009.
On December 16, 2009, Raiders Head Coach Tom Cable named Frye the starting quarterback of the Oakland Raiders after Bruce Gradkowski was injured with two torn MCL's. Frye surpassed former starter and number one overall draft pick JaMarcus Russell after Russell was sacked six times in relief of Gradkowski the previous week in a game against the Washington Redskins.
On December 20, 2009, Frye made his first start against the Denver Broncos, but was injured early in the fourth quarter and JaMarcus Russell came in to win the game.
Frye came back from his injury to play the next two weeks against the Cleveland Browns and Baltimore Ravens. Frye threw 3 interceptions but came back against the Ravens to throw a touchdown and no interceptions. Frye finished the season with 581 yards passing, 1 TD, and 4 INT with a 65.3 passer rating.
Frye signed a 1-year and $1.2 million contract with a third round tender on March 15, 2010. During training camp later that year, Frye injured his wrist and had to undergo surgery. Oakland placed him on injured reserve on August 19, 2010.
After injuries and surgeries ended his career early, Frye turned to coaching. Former teammate Kenard Lang, who was by then the head football coach at Jones High School in Orlando, hired Frye as offensive coordinator.
Before the 2013 season, Lang and Frye were hired for the same positions at Wekiva High School in Orlando.
In honor of his #5 jersey and last name, Akron Mayor Don Plusquellic declared Friday, November 5, 2007 "Frye-day".