After graduating in 1983, and playing four years at Tennessee State University, Dent was drafted in the eighth round by the Bears, with 203rd overall pick in the 1983 NFL Draft. At 6 ft 5 in, 265 lb (120 kg), Dent was a great pass rusher who beat offensive tackles with his speed. He was part of the core of great players who made the Bears’ defenses of the 1980s legendary. Between 1984 and 1985, Dent recorded 34.5 sacks, while recording a team-record 17.5 sacks in the former season.

When the Bears went on to defeat the New England Patriots in 46-10 landslide in Super Bowl XX, Dent was selected as the game’s MVP. During the game, he shared 1.5 sacks, forced two fumbles, and blocked a pass. Dent made a mere $90,000 in base salary for his efforts in 1985. ($173,000 in 2007 dollars and just over $192,000 in 2012 dollars ). He was a featured soloist of the “Shuffling Crew” in the video, the “Super Bowl Shuffle” in 1985.

Dent would remain with the team until the end of the 1993 season, after the Bears had won just one playoff game since their loss to the San Francisco 49ers in the 1988 NFC Championship Game, and head coach Mike Ditka had been replaced by Dave Wannstedt.

Dent won another Super Bowl ring after spending the 1994 season under contract with the 49ers, though he spent almost the whole year injured. Injuries would continue to hamper Dent after his return to Chicago in 1995. He would spend 1996 and 1997 with the Indianapolis Colts and Philadelphia Eagles, respectively, playing the so-called designated pass rusher for them.

In addition to the Pro Football Hall of Fame, Dent was also inducted into the Georgia Sports Hall of Fame on February 15, 2008.

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. His induction speech was notable for omitting any mention of both Ditka and Chicago defensive coordinator Buddy Ryan. Since his retirement Dent has had a difficult relationship with Ditka because he publicly blamed Ditka for the Bears’ inability to repeat as Super Bowl champions.