Fair played college football at the University of Tennessee, part of the school's heralded 1994 signing class. During his freshman season in 1994, he tallied 41 tackles, an interception, and three passes broken up, and was named to the All-SEC Freshman team. The following season, he recorded 50 tackles, two interceptions, and four passes broken up. During his junior year in 1996, he recorded 33 tackles, four interceptions, and three passes broken up, and returned 29 punts for 400 yards and two touchdowns. During his senior season in 1997, Fair recorded 39 tackles, five interceptions, and nine passes broken up, and returned 19 punts for 272 yards, helping the Vols win the SEC Championship. He was named All-SEC in 1996 and 1997.
NFL
Fair was drafted in the first round by the Detroit Lions in the 1998 NFL Draft. During his rookie year with the Lions, he tallied 39 tackles, including one sack, and led the NFL in kick return average with 28 yards per return. He returned two kickoffs for a touchdown, including a season-long 105-yarder against Tampa Bay on Monday Night Football. He was named to the NFL All-Rookie team by the Sporting News and Pro Football Writers Association. During his second season in 1999, Fair recorded three interceptions, including a 41-yard pick six against Minnesota, and averaged 22.1 yards on 34 kick returns. In 2000, he intercepted two passes, returned six kickoffs for 149 yards, and returned two punts for 15 yards. In 2001, Fair registered 43 tackles and intercepted two passes, including a 26-yard pick six against Cleveland, though he struggled with a foot injury during the latter part of the season. After being released by the Lions in 2002, Fair signed with the Carolina Panthers, but played only three games before a broken ankle ended his season. He was subsequently released by the Panthers, and spent the 2003 season recovering in Phoenix. In 2004, he signed with the Pittsburgh Steelers, but was cut prior to the season. Fair signed with the St. Louis Rams in 2005, but played in only five games due to injuries.
Coaching
After retiring from the NFL, Fair joined the coaching staff at Phoenix College. Four of his players went on to join Division I programs. He also co-hosted The Drive, a sports talk radio show that aired on WNOX in Knoxville. In 2010, he obtained a degree in psychology from the University of Tennessee. In 2013, Fair joined Butch Jones's staff at Tennessee as a defensive quality control assistant. Fair served as the cornerbacks coach on the staff of Mike Bobo at Colorado State from 2015 to 2017. In December 2017, Fair returned to his alma mater, the University of Tennessee, joining the staff of newly hired head coach Jeremy Pruitt. On February 8, 2019 Tennessee parted ways with Fair.
Personal
Fair and his wife, Sherlone, have three children together, Herandre, Delan, and Ariyah.