After playing four years at Tennessee State University and graduating in 1983, Dent was selected in the eighth round by the Bears, with the 203rd overall pick in the 1983 NFL draft.

[1] When the Bears went on to defeat the New England Patriots in a 46–10 landslide in Super Bowl XX,[2] Dent was selected as the game's MVP.

Dent won another Super Bowl ring after spending the 1994 season under contract with the 49ers, though he spent almost the whole year injured.

[5] Dent was nominated numerous times for the Pro Football Hall of Fame and in 2005–2009 he was among the top 15 finalists in the selection process.

After several years of unsuccessful nominations, he was finally selected for enshrinement in the Pro Football Hall of Fame in Canton, Ohio on February 5, 2011.

In a 2012 interview on WSCR, Dent argued that the Bears would have won at least three Super Bowls if they had been able to find any consistency at quarterback.