Fryman was born in Lexington, Kentucky, to Bill Fryman, a basketball coach and tire store manager. The family moved to Pensacola, Florida, when Fryman was three years old, and variously lived in Pensacola and Orlando. Fryman attended a Baptist church every Sunday as a child. He led Gonzalez Tate High School to a Florida high-school championship over Lake Mary High School at Rollins College in 1986.

The Detroit Tigers drafted Fryman in the first round of the 1987 Major League Baseball draft out of Tate High School in Pensacola. He debuted with the Tigers at Tiger Stadium on July 7, 1990, in a 4–0 loss to the Kansas City Royals, playing shortstop, but ended up seeing more time at third over the course of his first season in the majors.

Fryman split time between short and third in 1991 before an injury to Alan Trammell allowed him to inherit the starting shortstop job in 1992. He hit 20 home runs and drove in 96 runs to earn his first All-Star selection, and win the American League Silver Slugger Award at his position.

Fryman batted .287 with 28 home runs and 96 RBIs his first season in Cleveland to help lead his team to the American League Central division crown. Fryman batted only .167 with no RBIs and committed one error in the field in his first post-season as the Indians were ousted in the 1998 American League Championship Series by the New York Yankees.

Injuries hampered Fryman in 1999. He rebounded to have his best season in 2000. He established career highs in batting average (.321), slugging percentage (.516), on-base percentage (.392), hits (184), doubles, and RBIs (106). Additionally, he also only made eight errors in the field and had a 60-game errorless streak, on his way to winning a Gold Glove Award. His teammates rewarded his efforts with the Gordon Cobbledick Golden Tomahawk Award, and the Cleveland Baseball Writers’ Association named him their Man of the Year.

Injuries once again limited Fryman in 2001, as he did not make his first appearance until June 2. In 2002, he had the lowest range factor of all major league third basemen (2.31), as well as the lowest zone rating (.680).

Fryman became the manager of the Mahoning Valley Scrappers, the short-season A affiliate of the Indians in the New York–Penn League, in 2008. It was his managerial debut after having worked as an infield instructor with the Indians during spring training that year. Fryman has been mentioned as a possible manager for the Cleveland Indians. David Wallace became the Scrappers’ manager in 2011.