Jackson was born in Gainesville, Florida in 1971. He attended P. K. Yonge High School in Gainesville, where he was standout high school football player for the P. K. Yonge Blue Wave. He played as a quarterback, running back, wingback and defensive back. He received All-state honors as a senior, rushing for 427 yards and making 27 receptions.
College career
Jackson accepted a football scholarship to attend the University of Florida in Gainesville, where he played for coach Steve Spurrier's Florida Gators football team from 1990 to 1993. After being redshirted, he appeared in 5 games as a freshman but did not record a reception. As a sophomore, he posted 51 receptions for 725 yards and 10 touchdowns. Against Auburn University he had career-highs of 12 receptions and 157 yards. Against the University of Georgia, he became the fifth player in school history to make 3 touchdown receptions in one game. In the 1992 Sugar Bowl against the University of Notre Dame, he had the second best total yardage in Gators bowl history, with 8 receptions for 148 yards. As a junior, he had one of the best receiving seasons in school history, posting 62 receptions, 772 yards and 8 touchdowns, including a career-high 70-yard touchdown reception in the SEC Championship game against the University of Alabama. As a senior, he started only 9 games and missed the game against the University of Tennessee with a sprained left knee. He finished second on the team with 49 receptions for 675 yards and 6 touchdowns. Jackson led the team in receiving in 1991 and 1992, and was a first-team All-Southeastern Conference selection in 1992, and an honorable mention All-American in 1991, 1992 and 1993. Memorably, he had 148 receiving yards against the Notre Dame Fighting Irish in the 1992 Sugar Bowl and 130 yards against the West Virginia Mountaineers in the 1994 Sugar Bowl. Jackson finished his college career with 162 receptions for 2,172 yards and twenty-four touchdowns—still fifth on the Gators' all-time receiving yardage list. He also walked-on to the Florida Gators men's basketball team in the 1989-90 season, averaging 3 points per game and making 20 steals. He graduated from Florida with a bachelor's degree in telecommunications in 1993, and was inducted into the University of Florida Athletic Hall of Fame as a "Gator Great" in 2008.
Professional career
Jackson was selected by the Dallas Cowboys in the fourth round of the 1994 NFL Draft. After being inactive during all of the season, he asked the team to leave him unprotected in the 1995 NFL Expansion Draft, so he could get an opportunity to play in another place and not be a reserve behind Michael Irvin. In, the NFL's two new expansion teams, the Carolina Panthers and the Jacksonville Jaguars, participated in the 1995 NFL Expansion Draft, an opportunity to pick available players from the rosters of the existing NFL teams. The Jaguars picked Jackson from the Cowboys' unprotected list as the twenty-first overall pick in the expansion draft. In their inaugural season, he led the team in receiving with 53 receptions for 589 yards and 5 touchdowns, while starting in 10 contests. In, he posted 33 receptions for 486 yards and 3 receiving touchdowns. In, his stats diminished, coinciding with the explosion in the production of wide receivers Jimmy Smith and Keenan McCardell. He was waived on August 30,. He compiled 103 catches for 1,281 yards and ten touchdowns during his time with the club. Jackson signed with the Cincinnati Bengals on September 10,. He was declared inactive in 6 games. In, he ranked third on the team with 31 receptions for 369 yards and 2 touchdowns. On April 2,, he signed as a free agent with the New Orleans Saints. He started the last 6 games of the season, he ranked third on the team with 37 receptions for 523 yards and 6 touchdowns. In, he ranked second on the team with eighty-one catches for 1,046 yards and five touchdowns in sixteen starts. On July 12,, he signed with the Atlanta Falcons taking the place of the previously released Jeff Graham. He saw little playing time and was waived on October 28, 2002. On October 31, 2002, he signed with the Washington Redskins, reuniting with his former college coach, Steve Spurrier, then head coach of the team. He appeared in 5 games with one start and was cut on December 12. On March 12,, he signed with the Denver Broncos and was released before the season started on August 17. Jackson finished his eight-season NFL career with 284 receptions for 3,641 yards and twenty-four touchdowns.
Coaching career
In November 2018, Jackson was hired by his former college head coach Steve Spurrier as the wide receivers coach for the Orlando Apollos of the Alliance of American Football. He remained with the team until the league folded.
Personal life
Jackson's younger brother, Terry Jackson, was a tailback for the Gators from 1995 to 1998, and played running back and special teams for the San Francisco 49ers from to. His father, Willie Jackson, Sr., led the Gators in all-purpose yards and kick-off returns in the early 1970s, and was one of the team's first two African-American players at the University of Florida. All three Jacksons wore jersey No. 22 for the Gators.