He played in Major League Baseball (MLB) from 1975 to 1985 as an infielder for the Cincinnati Reds, New York Mets, Texas Rangers, Montreal Expos and the Detroit Tigers.

He attended Bryan Station High School, where he starred in baseball, basketball and football, playing quarterback on a 12–1 team.

[2] Despite having played shortstop predominantly in the minors, Flynn went into Spring training 1975 battling Darrell Chaney, Dan Driessen and John Vukovich for the open third base job.

[3] Starting the following night, Flynn scored his first major league run after reaching on a force play on the fourth inning.

With Reds third basemen batting a combined .162, Anderson shifted perennial All-Star and former National League MVP Pete Rose to third, with George Foster taking over in left.

He hit his first major league home run on May 21 against the New York Mets, a game in which Tom Seaver was the losing pitcher.

He ended up appearing in 93 games for the "Big Red Machine", as they became affectionately called, and batted .283 with one home run and twenty RBIs.

[9] On Wednesday, June 15, 1977, Grant traded Seaver to the Cincinnati Reds for Steve Henderson, Dan Norman, Pat Zachry and Flynn.

[10] Flynn's playing time increased substantially upon his arrival in New York City, even though he batted just .191 with no home runs and fourteen RBIs.

Just as pitchers and catchers were reporting to Spring training, the Mets sold the contract of second baseman Félix Millán to the Taiyo Whales of Nippon Professional Baseball[11] with the intention of using Flynn at second.

Flynn's first home run as a Met was a three-run shot off future Hall of Famer Gaylord Perry on May 1, 1979.

With top prospect Wally Backman ready to make the jump to the majors, the Mets traded Flynn to the Texas Rangers with Dan Boitano for Jim Kern at the end of the season.

The Montreal Expos had used seven different players at second base, and were desperate need of an upgrade at that position when they purchased Flynn's contract from Texas on August 2.

[23] Flynn's father, Bobby, was a second baseman in the Brooklyn Dodgers' organization in 1948, and later played semi-pro ball with the Lexington Hustlers.

While his son was coming up through the Reds' minor league system, Bobby was also climbing politically, serving as Kentucky state senator.

[26] In 1981, Flynn began singing country songs at Cody's, a club at Sixth Avenue and 16th Street in Manhattan on Monday, Tuesday and Wednesday nights.

He still loves to sing and pairs up with former Reds teammate Johnny Bench at their successful golf tournament every year on cabaret night.